Adam Grossman

WHEN IT COMES to financial decisions, there are, as I’ve argued before, two answers to every question: what the calculator says, and how you feel about it. There’s a fly in the ointment, though: Calculator answers might appear to be based in logic, but they’re still imperfect.
Why?
Ian Wilson, a former executive at General Electric, explained it this way: “No amount of sophistication is going to allay the fact that all knowledge is about the past,

“INVESTING IS SIMPLE,” observed HumbleDollar’s editor Jonathan Clements. “To be sure, you can make it ludicrously complicated.” And, indeed, Wall Street does just that.
According to a recent analysis by Bloomberg, the fund industry rolled out more than 640 new exchange-traded funds (ETFs) in the first half of this year—an average of more than three a day. There are now more ETFs in the U.S. than there are stocks (4,300 vs. 4,200).

NEW RESEARCH CAN help with an age-old question: When constructing a portfolio, how much risk is too much? Especially today, with the market again near all-time highs, this is an important issue.
On the one hand, we could dismiss this concern by noting that all-time highs aren’t as uncommon as they might seem. According to one analysis, the U.S. stock market has been within 5% of an all-time high on 44% of trading days since the 1950s.

ANDREW CARNEGIE USED to say that competitors were welcome to tour his factory, to see his production line up close. Why? Because of Carnegie Steel’s massive scale and complex operations, he was confident no one would ever be able to replicate what he’d built.
Hedge fund manager Seth Klarman is a modern-day Carnegie. Klarman founded the Boston-based Baupost Group in 1982, and while performance numbers aren’t publicly available, the firm’s track record is believed to be among the best in the industry.

ONE OF THE MARKET’S worst-performing stocks over the past year was, not long ago, one of its best. Novo Nordisk is the Danish company that pioneered the hugely popular weight-loss drug Wegovy, also known as Ozempic. After it hit the market in 2021, the company’s stock rallied, tripling over the following three years. Since then, however, things have been far more challenging. Over the past 12 months, the stock has dropped 60%.
This highlights a key challenge for investors: On the one hand,

EARLIER THIS SUMMER, Congress passed the Guiding and Establishing National Innovation for U.S. Stablecoins Act—GENIUS, for short. This sounds obscure, but it’s a story worth following. The GENIUS Act’s purpose is to promote the growth of—and to regulate—a new type of financial instrument known as a stablecoin.
What’s a stablecoin? It’s similar to a cryptocurrency but differs in one important way: Bitcoin and other cryptocurrencies have exhibited wide price swings. That makes them interesting to investors but less-than-useful as currencies for everyday transactions.

IN THE ANCIENT WORLD, before the invention of the printing press, the most common way to retain information was to build what’s known as a memory palace. The idea was to link words to images, because images are easier to remember.
I’ve found that this strategy works well in personal finance, and earlier this year I described some of the images that I rely on most. Below are several more.
1. Back in 2011,

STOCK MARKET Investing requires a near superhuman ability to withstand pain. That’s the conclusion of a recent report by investment researcher Michael Mauboussin.
Mauboussin surveyed all stocks trading on U.S. exchanges over a 40-year period, between 1985 and 2024. He found that the median stock experienced a decline of 85% at one point or another. Worse yet, more than half of these stocks never fully recouped their losses. The median stock recovered to just 90% of its prior high-water mark.

A PLANE’S ALTIMETER measures the airplane’s altitude. It’s a critical instrument—so important, in fact, that planes are typically outfitted with two. That’s for redundancy, in case one fails. In addition, because different altimeters work better in different conditions, the two readings offer pilots multiple points of reference.
I was speaking recently with a retired pilot, who explained this to me and asked how he could apply the notion of redundancy to his finances. It was a good question,

OVER THE JULY FOURTH weekend, a friend asked me what I thought about the new financial instrument known as a “stock token.” Developed by the online broker Robinhood, a stock token is designed for investors to buy stakes in private companies such as OpenAI, creator of ChatGPT. It’s a novel concept because private company investments are typically inaccessible to individual investors.
Despite the appeal, I urged caution. Why? These tokens may not perform as expected because they aren’t the same as actual equity in a company.

ON DEC. 31, 1759, Arthur Guinness signed a lease to take over a defunct brewery in Dublin. What was unusual was the lease’s term: 9,000 years.
It didn’t take long before Guinness and his landlord both realized they’d made a mistake and agreed to end the lease. Guinness needed more space, and the landlord realized he’d neglected to account for inflation. The rent was fixed at £45 annually for the entire 9,000 years.
The Guinness case is notable because it’s so extreme,

IN A RECENT INTERVIEW, Dario Amodei, CEO of Anthropic, a leader in artificial intelligence, grabbed headlines. Amodei argued that the next generation of AI systems could replace half of entry-level jobs and drive up the unemployment rate to 20%. All of this could occur in the next five years, he said.
Recent data seem to support these glum predictions. Mark Zuckerberg said AI will be as capable as a mid-level programmer by the end of this year.

AT THE 2016 SUMMER Olympics in Rio de Janeiro, South Africa’s Chad Le Clos challenged Michael Phelps for the gold medal in the 200-meter butterfly. A famous image emerged from that event: Throughout the semifinal, Le Clos repeatedly looked over at Phelps as he struggled to keep up. Meanwhile, Phelps just kept looking forward. The result: Phelps ultimately won the gold, while Le Clos trailed in fourth place.
I believe there’s a parallel between what we saw in that race and what we see in the investment world.

STATISTICIAN GEORGE E.P. Box once made this observation: “All models are wrong,” he said, “but some are useful.” This certainly applies to finance, where many of the concepts are imperfect but can nonetheless still be useful. Below are four such examples.
Market valuation. Are stocks overpriced? It’s a question without an easy answer. Even academics who have studied the topic can never be entirely sure. Consider the cyclically adjusted price-earnings (CAPE) ratio.

LAST WEEK, I MENTIONED the 17th century Dutch tulip bubble. There’s a lot we can learn from history. Current events, however, can teach us just as much. Below are three valuable lessons I see in today’s market.
Myopia. Open any finance textbook, and you’ll find that most of its ideas are built on the notion of “present value.” This simply means an investment should be worth the sum of its future cash flows.

BITCOIN HIT A NEW high last week, topping $112,000. Over the past 12 months, it’s climbed an impressive 55%.
What’s driving this gain, and what should you make of it? I believe there are three key factors. Two are new. One is not.
The first factor was a policy change last year. The federal government approved the launch of new exchange-traded funds (ETFs) that offer easier and more direct access to bitcoin. Following this rule change,

IF THE NAME LIZ TRUSS sounds vaguely familiar, there’s a reason: Truss was once the prime minister of the U.K.—but for just 45 days.
How did Truss lose public confidence so quickly? The bond market forced her out. Shortly after taking office in the fall of 2022, Truss proposed substantial tax cuts for both corporations and individuals. That would have been a popular move, except that her budget didn’t include any offsetting spending cuts.

WHEN HUMBLEDOLLAR’S editor was The Wall Street Journal’s longtime personal-finance columnist and his children were little, he often joked that he had a special incentive to see them succeed financially.
“It would be a tad embarrassing,” Jonathan wrote, if his children “grew up to be financial ne’er-do-wells.” For that reason, he used his own home as a laboratory of sorts, testing strategies to help set his children on the right financial path.

IT’S BEEN QUITE A YEAR for gold investors. While the stock market has struggled, gold hit a new all-time high, topping $3,500 per ounce just a few weeks ago.  Year-to-date, gold has gained nearly 30%, while the S&P 500 is in negative territory. This has certainly grabbed people’s attention—but does gold make sense for your portfolio?
To answer this question, let’s start by looking at the arguments favoring gold. Supporters typically point to two key attributes,

ABOUT 10 YEARS AGO, Steve Edmundson, manager of the Nevada state pension, became a folk hero in the investment world when The Wall Street Journal profiled him in an article titled, “What Does Nevada’s $35 Billion Fund Manager Do All Day? Nothing.”
It was an exaggeration to say he did “nothing,” but Edmundson definitely did things differently. Since the 1980s, the trend among pension and endowment managers had been to follow in the footsteps of Yale University’s David Swensen.

FRENCH HISTORIAN Alexis de Tocqueville toured the U.S. in the 1830s and chronicled his observations in a book titled Democracy in America. What mainly impressed him was Americans’ focus on trade and commerce.
They have a “purely practical” mindset, he wrote, and concluded that “the position of the American is quite exceptional.” In the years since, others have picked up on this concept of “American exceptionalism.”
Despite recent political and economic crosscurrents,

IT’S BEEN AN UNUSUAL year—to say the least—for investment markets. After rising earlier in the year, U.S. stocks and bonds have dropped in recent weeks. Market leaders like Apple and Nvidia have been among the hardest hit. The U.S. dollar has also dropped, helping boost the value of international shares, and gold has continued to hit new all-time highs, despite inflation cooling.
What can we learn from all this? I see seven lessons.
1.

YOU MAY BE FAMILIAR with Peter Lynch. In the 1970s and ‘80s, he was one of the most visible figures in the investment world. As manager of Fidelity Magellan Fund, he achieved the best track record, by far, among his peers. He shared his wisdom in a series of popular books for individual investors.
Among the ideas for which Lynch is best known is the notion of “diworsification.” As its name suggests, Lynch argued that diversification simply for the sake of diversification isn’t always a good thing.

WHEN STEWART MOTT graduated college in 1961, he received $6 million from his father, an auto industry entrepreneur who was one of the founders of General Motors. On top of the $6 million, a family trust began paying Mott an annual stipend of $850,000.
That allowed Mott to spend his adult life pursuing a variety of eccentric endeavors. He funded research on extrasensory perception. Inside his Manhattan apartment, he built a 10,000-square-foot garden, along with a chicken coop.

OSCAR WILDE ONCE made this observation: “Education is an admirable thing, but it is well to remember from time to time that nothing that is worth knowing can be taught.” In other words, the only way to truly learn something is through experience.
When it comes to investing, this is easier said than done because learning through experience can be expensive. As Warren Buffett once quipped, “It is good to learn from your mistakes.

IN 1774, AMSTERDAM businessman Abraham van Ketwich created a new type of investment. After raising money from a group of individuals, van Ketwich built a portfolio of bonds. He deposited the bonds in a metal box in his office, which three people then secured using three different locks.
Van Ketwich’s fund could be considered the world’s first index fund. How so? For starters, the bonds purchased were broadly diversified across industries and geography. Second,

IN THE ANCIENT WORLD, before the invention of the printing press, a strategy for remembering information was to build a so-called memory palace. The idea was to associate words with images. Even today, this is how participants in memory competitions can achieve feats like reciting a thousand digits of pi.
Similarly, when it comes to personal finance, I’ve found that certain images can help illustrate important concepts. These are the ones I rely on the most:
1.

IN THE 1990s, Mark Cuban started one of the first internet companies, a video streaming service called Broadcast.com, and later sold it to Yahoo for several billion dollars. With some of the proceeds, he bought the Dallas Mavericks NBA franchise and sold that as well, taking home another several billion dollars.
And for 16 seasons, Cuban appeared on the reality TV show Shark Tank, in which entrepreneurs present ideas to a panel of prospective investors.

NINE MONTHS AGO, Jonathan Clements shared with readers that he’d been diagnosed with an incurable form of cancer. It was devastating news, especially for longtime readers, many of whom regard Jonathan not only as a journalist but also a friend. I count myself among them, so I was grateful that Jonathan agreed to sit for an interview to share more about his background, his early years and his current thinking. 
You’ve joked that,

THE U.S. STOCK MARKET has historically delivered similar returns under both Democrat and Republican administrations. For that reason, my view is that investors shouldn’t worry too much about who occupies the White House, and I tend to stay away from investment discussions that involve politics.
But sometimes, the news coming out of Washington dominates the headlines in a way that can’t be ignored. Such is the case today. Moreover, with the stock market faltering recently,

THIS MONTH MARKS the five-year anniversary of the start of the pandemic. That makes this a good time to look back and ask what lessons we might learn.
In early 2020, when COVID-19 was first identified in the U.S., the stock market dropped 34% in the space of just five weeks. But later in the year—after the Federal Reserve stepped in with its bazooka—the market rebounded, ending the year in positive territory. For full-year 2020,

THERE’S A CHANGE coming in the way many of us invest. But for background, it’s important first to look at a related—though seemingly mundane—investment concept known as tax-loss harvesting.
To understand how tax-loss harvesting works, consider a simple example. Suppose you purchased a stock in your taxable account for $10, and it subsequently dropped to $8. That would be unfortunate, but there’d be a silver lining: You could sell the stock to capture the $2 loss for tax purposes and then reinvest the proceeds in another stock.

FIFTY YEARS AGO, when the first index funds were getting started, critics wasted no time attacking the idea. They called it “un-American” and a “sure path to mediocrity.”
But over time, indexing has grown to the point where it now accounts for more than half of all U.S. mutual fund assets. Last year, research firm Morningstar declared that “index funds have officially won.” But this victory seems to have only increased the level of criticism.

MARVIN STEINBERG was a psychologist who founded the Connecticut Council on Problem Gambling. During his career, he made some uncomfortable observations about the behavior of stock market investors. In many cases, he felt, investors’ behavior veered awfully close to gambling.
This is the sort of observation that seems like it could be true, but it also seems difficult to quantify. That’s why a recent study by Morningstar analyst Jeffrey Ptak caught my eye.
Ptak wanted to examine investors’ experience with so-called thematic funds.

IN WASHINGTON, 2025 is beginning to look a lot like 2017. Republicans again control the White House, the Senate and the House of Representatives. But a key difference between then and now is that today the Republican majority in the House is far narrower.
This means more negotiation will be required, and agreement on a new tax bill may take months. In the meantime, here are some key areas that investors will want to keep an eye on.

A QUOTE OFTEN attributed to Mark Twain goes as follows: “It ain’t what you don’t know that gets you into trouble. It’s what you know for sure that just ain’t so.”
This certainly applies to personal finance, and it’s why it can be helpful to take a step back sometimes to revisit widely held notions—including these six.
1. Social Security. You may have heard of Social Security’s “earnings test,” which can reduce the size of monthly checks for those who continue working after claiming benefits.

MICHAEL BURRY IS a hedge fund manager who gained fame betting against the housing market in 2008. When that market collapsed, Burry made a fortune, and that cemented his reputation as a market seer. Burry was later portrayed as the central character in Michael Lewis’s The Big Short.
But in the years since, Burry’s predictions haven’t turned out as well. Five years ago, he spooked index-fund investors when he argued that they might have trouble accessing their funds.

ONE SPRING DAY IN 2022, an elderly woman entered Paris’s Picasso Museum to see a new exhibit. Among the items on display was a decorative blue jacket, which was positioned on a wall next to a portrait of Picasso.
The woman liked the look of the jacket, so she took it down from its hook, put it in her bag and quietly walked out the front door. Only later did the museum discover the theft,

IN THE FINANCIAL world, some topics are serious, others not so much. Since it’s the holiday season, it seems appropriate to look back at some of the past year’s lighter moments.
No joke. In 2019, artist Maurizio Cattelan unveiled a collection he called Comedian. The item that received the most attention: a sculpture that consisted only of a banana duct-taped to a wall. The banana gained fame when it sold at a Miami auction for $120,000.

EARLY LAST WEEK, The Wall Street Journal ran an article with the headline “Why This Frothy Market Has Me Scared.” The author cited a number of indicators that have him worried, including a survey of investor optimism that’s at a 35-year high. Investors, the Journal said, are feeling “euphoric,” and that’s often a bad sign.
So, as we head into year-end, it’s worth taking stock of where things stand. The stock market has returned nearly 25% so far this year.

LOOKING TO CONDUCT a review of your investments? Below is a five-point end-of-year housekeeping checklist.
Suitability. When it comes to the world of investments, the most common types of assets are stocks and bonds—but they aren’t the only ones. There are alternatives like real estate and commodities and, of course, there’s bitcoin, which has more than doubled this year. Which of these is right for you? Since everyone is different, the first litmus test is to assess the suitability of the types of assets you own.

IMAGINE TAKING DOLLAR bills and inserting them into a shredder. This is how you might think about a concept that economists call “deadweight loss.” As its name suggests, a deadweight loss occurs when there’s an irrevocable loss of economic output.
Deadweight losses can occur under a variety of circumstances. Among them: when tariffs are imposed. It’s for that reason that the incoming administration’s tariff plan has raised concerns. But how worried should we be?

MORGAN HOUSEL, author of The Psychology of Money, once made this observation: “Before the 1700s, the richest members of society had among the shortest lives—meaningfully below that of the overall population.”
It was counterintuitive, but Housel cited a hypothesis, developed by historian T.H. Hollingsworth, to make sense of it: “The best explanation is that the rich were the only ones who could afford all the quack medicines and sham doctors who peddled hope but increased your odds of being poisoned.”
Housel then added this thought: “I would bet good money the same happens today with investing advice.” Wealthy folks,

BENJAMIN GRAHAM, the father of investment analysis, made this observation: “The investor’s chief problem—even his worst enemy—is likely to be himself.”
Why? One reason is our intuition can sometimes lead us astray. Things that seem like they make sense, and seem like they ought to be true, often turn out not to be supported by the data.
Perhaps the best-known example is the divergence between growth and value stocks. Intuition suggests that growth stocks—companies like Apple and Amazon—would deliver better performance than their more pedestrian peers on the value side of the market.

THE JUNE 16, 2021, edition of The Washington Post carried this headline: “Cristiano Ronaldo snubbed Coca-Cola. The company’s market value fell $4 billion.”
The incident in question had occurred a few days earlier, at a press conference in Budapest, where the soccer star was set to play in a high-profile championship game. Coca-Cola was a sponsor of the tournament, so when Ronaldo sat down at the microphone, he found two bottles of Coke positioned in front of him.

BEFORE HE DIED LAST year at age 99, a friend asked Charlie Munger if he planned to leave his considerable wealth to his children. Wouldn’t it impact their work ethic, his friend asked?
“Of course, it will,” Munger replied. “But you still have to do it.”
“Why?” his friend asked.
“Because if you don’t give them the money, they’ll hate you.”
Few of us are billionaires. Still, I find Munger’s comment instructive. It illustrates a reality about personal finance: that the notion of a perfectly optimal answer to any financial question is just that—a notion.

AN ANCIENT FINANCIAL concept is gaining newfound popularity.
In his book Politics, Aristotle related a story about a fellow philosopher named Thales, who lived about 2,600 years ago. One winter, Thales made a prediction about the coming olive harvest. He felt that it was going to be a strong year. But because recent harvests had been weak, most people disagreed with him. To Thales, this meant opportunity. He approached the owners of olive presses in his town with a proposition.

THE NEIGHBORING TOWNS of Nogales, Arizona, and Nogales, Mexico, figure prominently in the work of Daron Acemoglu and James Robinson, who—together with a colleague—won this year’s Nobel Prize in economics.
In their book Why Nations Fail, Acemoglu and Robinson explain that these two border towns are identical in almost every way—from demographics to geography to climate. But they differ in one key respect: Nogales on the American side of the border is prosperous, while its southern neighbor is not.

FOR YEARS, THERE’S been growing concern about the top-heavy nature of the U.S. market. Today, just 10 stocks account for 35% of the S&P 500’s total value. And while the largest technology stocks—dubbed the Magnificent Seven—have done exceedingly well in recent years, their extreme outperformance is making people nervous.
Observers are comparing today’s market to past periods when certain groups of stocks appeared similarly flawless. Consider the late 1990s, when companies such as General Electric dominated the market.

BENJAMIN GRAHAM was Warren Buffett’s teacher and mentor. He also ran an investment fund that specialized in uncovering demonstrably undervalued stocks.
One day in 1926, Graham was at his desk, reading through a government report on railroads, when he noticed a potentially important footnote. It referenced assets held by a number of oil pipeline companies. But there wasn’t a lot of detail, so Graham boarded a train to Washington and found his way to the Interstate Commerce Commission (ICC),

IS IT WORTH OWNING international stocks? There’s far from universal agreement. The traditional argument for investing outside the U.S. is straightforward: diversification—since domestic and international stocks don’t move in lockstep, and sometimes diverge significantly.
At the same time, however, international stocks have lagged behind their U.S. counterparts for so many years that it’s been trying the patience of even the most tenacious investors. Domestic stocks have outpaced international stocks in eight of the past 10 years.

A RECENTLY RELEASED book titled How to Retire is a goldmine for those in or near retirement. For the book, Christine Benz—Morningstar’s director of personal finance and retirement planning—conducted interviews with 20 experts, covering every aspect of retirement.
The result is a valuable field guide for those tackling life after work. Below are seven insights I found particularly useful.
1. Social connections. When we think about retirement planning, most of us tend to think first about the numbers.

SOME YEARS AGO, an elderly neighbor came to our door, asking for a favor. She was looking for packing tape because she’d sold her television and needed to ship it. She went on to say that the buyer, who she’d found on eBay, was in Nigeria. It was, of course, an obvious scam. But for whatever reason, she couldn’t see it.
Today, scams like this are better known and easier to recognize. But what makes online fraud such a problem is that the crooks are always developing new tricks.

WHY IS IT THAT GREAT companies don’t always make great investments? This is a conundrum that’s long puzzled investors because it so clearly flies in the face of intuition.
Indeed, today’s market leaders—companies like Apple, Amazon and Microsoft—are impressive businesses, and their stocks have delivered equally impressive performance, so much so that they and their peers have been dubbed the “Magnificent Seven.” The others in this group are Google parent Alphabet, Facebook parent Meta,

ABOUT ONCE A WEEK, someone will say to me, “I don’t understand bonds.” Sometimes, they’ll state it in stronger terms: “I don’t like bonds.”
Fundamentally, bonds are just IOUs. If you buy a $1,000 Treasury bond, you’re simply lending the government $1,000. The Treasury will then pay you interest twice a year and return your $1,000 when the bond matures. That part is straightforward. What’s more of a mystery is why we should own bonds and what we should expect from them.

COULD SOMETHING like the Great Depression happen again? During that unpleasant episode, the stock market dropped 90%, unemployment rose to 25% and gross domestic product fell 30%. In making a financial plan, is this a scenario we should worry about?
While no one can predict the future, it’s worth taking a closer look at one key variable: the Federal Reserve. Today, the Fed has a reputation for helping smooth out economic cycles. But those who worry about Depression-like scenarios point out how powerless the Fed was to prevent the collapse that occurred in the 1920s and 30s.

DIVIDENDS ARE a seemingly mundane topic. But like many areas of personal finance, it’s one that still generates debate. The most common question: All else being equal, if one stock pays a dividend and another doesn’t, shouldn’t an investor prefer the one that pays the dividend? We’ll examine this question, and then broaden the lens to look at dividend strategies more generally.
To better understand how dividends work, let’s look at Procter & Gamble.

MONEY MANAGERS Raj Rajaratnam and Joel Greenblatt share a number of similarities. They’re almost exactly the same age. Both received business degrees from the University of Pennsylvania, and both started well-known hedge funds. But the similarities end there.
During the 10 years that Greenblatt operated his fund, Gotham Capital, it delivered returns averaging 50% a year, versus 10% for the S&P 500. Thanks to his success, Greenblatt retired from full-time work in 1994 at age 37.

MARKET OBSERVERS have been predicting a recession for the past two years. Why? They’ve pointed to what’s known as an inverted yield curve, when short-term interest rates are higher than long-term rates. Historically, this has been a bad omen for the economy. The yield curve has been inverted since 2022—and yet, despite that, the economy has remained strong and stock markets have continued to hit new highs.
That all changed on Aug. 2, when a little-known indicator known as the Sahm rule began flashing red.

BONDS MAY NOT BE the most interesting investment, but they generate their fair share of debate. Especially after 2022’s rout, when total-bond market funds dropped 13%, many investors wonder how best to proceed. An open question: Does it make more sense to buy individual bonds or opt for bond funds?
To answer this question, let’s start with a simple example. Suppose you’d invested in Vanguard Group’s total-bond market fund (symbol: BND) on Jan. 1,

AMONG THE FINANCIAL topics grabbing investors’ attention, inflation for many years was near the bottom of the list. In fact, between 2010 and 2019, inflation averaged just 1.8% a year, and the Federal Reserve was looking to lift that rate. Throughout 2019, the Fed lowered its benchmark interest rate multiple times, citing inflation that was running below its preferred level of 2%.

But just a few years later, in the midst of the pandemic, all that changed.

SUPPOSE YOU WANTED to construct as simple an investment portfolio as possible. What would it look like?
Many argue that, for stock market exposure, you could go with a single fund, one that tracks the S&P 500 index. The S&P index offers broad diversification and tax efficiency, plus it includes the largest and most successful companies, making it a popular choice. But it’s not perfect.
The S&P 500, like many market indexes, holds stocks in proportion to their size,

A NEW TYPE OF MUTUAL fund has captured investors’ attention. Known as buffer funds, they’re so appealing that one industry analyst has referred to them as “candy.” Why? As The Wall Street Journal describes them, buffer funds offer investors “the chance to chase stock returns while also protecting against a potential market slide”—a seemingly ideal combination, especially for those in or near retirement.
But funds like this are complicated—they rely on options strategies.

FROM THE COLOSSEUM in Rome to the palace at Versailles, look around Europe and you’ll find artifacts of once-great empires. What happened to them?
Each faced its own challenges, but there was also a common theme: They had poor financial management and became overburdened by debt. That’s why a recent analysis in The Wall Street Journal—titled “Will Debt Sink the American Empire?”—is worth our attention.
In 2024, the federal government’s budget deficit will come in at $1.9 trillion.

THE YEAR’S MIDPOINT is here, with the stock market on track for its second consecutive year of above-average gains. This has many investors asking about rebalancing. Below are some commonly asked questions.
What is rebalancing? Let’s say that, to get the right mix of risk and return, you’ve settled on an asset allocation of 50% stocks and 50% bonds. Now, suppose the stock market rises 10%. This would lift stocks to some 52% of your total portfolio,

BACK IN 1987, Nassim Nicholas Taleb was a trader on Wall Street. But unlike most of his peers, Taleb wasn’t pinning his hopes on a market rally. Instead, he’d positioned himself to benefit from a market meltdown. On Oct. 19, just such an event occurred. For no apparent reason—in the midst of an otherwise strong market—the S&P 500 dropped 23% in a single day. The result: Taleb made a fortune—enough to retire at age 27.

ARE HEDGE FUNDS a good investment? To answer this question, let’s take a look at three well-known funds. The first is Renaissance Technologies.
Renaissance was founded in 1982 by academic James Simons, who’d been chair of the math department at Stony Brook University and, before that, a code-breaker for the U.S. military. Because he didn’t have a background in finance, Simons instead relied on mathematics, developing the first purely computer-driven trading system.
The result: As his biographer put it,

BRITISH PHILOSOPHER G.K. Chesterton, in his 1929 book The Thing, introduced an idea now known as “Chesterton’s fence.”
Here’s how he explained it: Imagine two people walking along a road when they discover a fence blocking the way for no apparent reason. As Chesterton tells it, the first person looks at the fence and says, “I don’t see the use of this; let us clear it away.” But the second person disagrees: “If you don’t see the use of it,

PEOPLE DEBATE JUST about everything in personal finance. Among these arguments: how best to measure risk. Partisans on this topic tend to fall into one of two camps.
In the first group are those who believe risk can be distilled down to a single number. For these folks, the most common numerical yardstick is portfolio volatility—that is, the degree to which a portfolio’s price bounces around from year to year. Portfolios exhibiting lower volatility are deemed safer.

IN THE INVESTMENT world, there’s no shortage of data. But how useful is all that data? To help get to an answer, let’s consider four questions:
1. When the economy is strong, is that good for stocks? The simple answer is “yes.” According to textbook finance, the value of any company should represent the sum total of its future profits. When the economy is strong and profits are higher, that should be good for stocks.

IN THEIR NEW BOOK The Missing Billionaires, Victor Haghani and James White make an interesting argument. Looking at the number of millionaires in the U.S. in 1900 and doing some math, they estimate that there should be many more billionaires today—thousands more, in fact—than there are. The question Haghani and White ask: Where did they go? Or, more specifically, where did their wealth go?
The authors consider possible explanations, including taxes—especially estate taxes—and the 1929 crash.

MICK JAGGER IS AMONG the most successful entertainers of our time. But despite his wealth, Jagger tells his eight children that they’ll need to make their own way. Similarly, Shaquille O’Neal tells his children that they can earn some of his millions, but it won’t necessarily be given to them. Actor Jeff Goldblum puts it more bluntly: “Row your own boat,” he’s said. Other public figures have echoed a similar theme.
Why do these wealthy folks take such a seemingly uncharitable view?

AMONG THE MORE notable studies published in recent years is a paper by Hendrik Bessembinder titled “Do Stocks Outperform Treasury Bills?” His key finding: Between 1926 and 2016, just 4% of stocks accounted for all of the U.S. market’s net gain. As a group, the other 96% delivered returns that were no better than Treasury bills, which returned just 2% a year over the period.

It was a surprising result. The implication: Diversification is even more important than most investors realized,

“IT’S TOUGH TO MAKE predictions, especially about the future.” That’s one of the more amusing quotes attributed to Yogi Berra, but there’s also a lot of truth to it. When it comes to financial markets, the track record of those making forecasts is not good.
That’s why a rational approach to decision making is to avoid predictions, and instead base choices only on an assessment of where things currently stand. But even that approach can be fraught: Financial trends have a habit of reversing when least expected.

LAST WEEK, I DISCUSSED a key challenge in personal finance: In an endeavor where we’d expect facts and logic to drive decisions, we instead find that misconceptions and misunderstandings often take hold. In my previous article, I outlined five common financial myths. Below are five more:
1. “When a company’s doing well, its stock should go up.” Benjamin Graham, the father of investment analysis, was famous for the way he explained stock market behavior: “In the short run,

YALE UNIVERSITY economist Robert Shiller, in his book Narrative Economics, argues that storytelling has more of an impact on economic events than we might imagine. It might seem like the financial world ought to be driven by facts and data, and yet stories often take on a life of their own.
For instance, financial narratives often play a key role in stock market bubbles and busts. More generally, financial myths and misperceptions are widespread,

GOLD REACHED A NEW high last week, climbing above $2,200 for the first time. Year-to-date, gold is up 8% and, since the end of 2021, it’s gained more than 20%, outpacing the S&P 500. This raises two questions: Can we expect the rally to continue? And does gold deserve a place in your portfolio?
To answer these questions, let’s start by looking at the drivers of the recent rally. The first factor is interest rates.

NICK MAGGIULLI, in his book Just Keep Buying, makes an observation about the world of personal finance: If you Google common questions—such as “how much should I save?”—you’ll receive more than 100,000 results. It’s an overwhelming amount of information. But there’s a bigger issue: Many of the answers contradict each other.
It’s the same with many other personal finance questions. How much should you hold in bonds? Do you need international stocks?

AMONG THE QUOTES wrongly attributed to Mark Twain is this one: “It ain’t what you don’t know that gets you into trouble. It’s what you know for sure that just ain’t so.”
This quip highlights one of the challenges of personal finance: that the data and the conclusions we rely on for decision-making can never be accepted with absolute certainty. That’s for a few reasons.
First, because the world changes and markets change, our approach must change as well.

RETIREMENT CAN—ironically—take work. It requires us to restructure how we think about both our time and our finances. That rethinking extends to tax planning, which tends to move to center stage once we quit the workforce. Already retired or approaching retirement? There are several tax strategies worth considering.
But before we review specific strategies, it’s worth pondering a more fundamental change wrought by retirement. During our working years, the usual goal is to minimize our tax bill each year.

MY FIRST DAY IN the investment industry was—unfortunately—not so great. On the morning of Sept. 15, 2008, the investment bank Lehman Brothers filed for bankruptcy, sending the stock market into a free fall. The rest of 2008 was equally ugly, with the S&P 500 losing 37% for the year. But that experience provided investors with a valuable lesson—about the power of recency bias.
Recency bias is the mind’s tendency to extrapolate. When things are terrible,

IN NEW ORLEANS, a lagniappe refers to a small gift or bonus—like receiving 13 items for the price of 12, or a so-called baker’s dozen. Today, credit card points are a popular form of lagniappe, delivering a modest bonus every time you spend. But many other lagniappes are also readily available:
Banking. If you’ve ever paid a fee to use an ATM, Charles Schwab Bank’s checking account is worth a look. You can use any bank’s ATMs and,

APPLE COMPUTER WAS founded on April 1, 1976, by Steve Jobs and Steve Wozniak. What’s less well known is that originally there was a third co-founder, an engineer named Ronald Wayne. Wayne’s tenure at the company was short, though. Concerned by the risk—and by Jobs’s personality—Wayne sold his stake in the company after just 12 days.
In exchange for his 10% stake, Wayne received $2,300. Today, Apple is worth close to $3 trillion. Wayne’s decision to sell is sometimes cited as one of the worst missteps in financial history.

THE S&P 500 INDEX just hit a new all-time high, topping 5,000 for the first time. Is it now too high? For investors concerned about market risk, this is an important question. But it isn’t an easy one to answer.
For starters, there’s no single definition of “too high.” Consider the price-to-earnings (P/E) ratio, the most common measure of market valuation. By this metric, the market does indeed look pricey. The P/E of the S&P 500 stands just a hair below 20 based on expected 12-month earnings—far above its 40-year average of 15.6.

WHEN I WAS A KID, a popular expression was “same difference.” It meant that two choices were essentially interchangeable. It turns out the idea can be helpful in financial planning.
While some financial decisions are very important—and thus warrant careful analysis—others make far less of a difference. In those cases, additional analysis typically contributes little. According to one study, it can even be counterproductive. Below are several topics where extensive analysis is often less important than it might seem.

RETIRED HEDGE FUND manager Jim Cramer is the host of Mad Money, a staple of financial television. For years, critics have derided his investment recommendations—to the point where there’s now a fund designed specifically to bet against him: the Inverse Cramer Tracker exchange-traded fund (symbol: SJIM).
For investors who see Cramer as the P.T. Barnum of finance, this fund offers the ability to make bets that are precisely the opposite of what Cramer recommends.

WITH 2024’S ELECTION underway, many folks are asking, do politics affect investment markets? On that score, there’s good news: The data say markets in the U.S. have delivered good—and roughly equal—results under both Democrats and Republicans.
But that doesn’t mean politics never has an impact. Look outside the U.S., and you’ll see that a country’s political structure can have enormous implications. To the extent that your portfolio is diversified internationally, it’s important to keep an eye on developments elsewhere.

CHARLIE MUNGER, WHO died recently at age 99, always had a colorful turn of phrase. But entertaining as he was, his comments were also invariably full of wisdom.
In fact, taken together, Munger’s ideas offered investors a masterclass in investing. Here are some highlights:
Choosing an investment strategy. Munger, along with his partner, Warren Buffett, often commented on the limits of his knowledge. But this wasn’t false modesty. What Munger was saying was that the universe of investments is too broad for any individual to fully master.

WHAT SHOULD BE THE first rule of personal finance? My vote: Always look for ways to stay in the center lane—that is, to take a balanced approach. As 2024 gets underway, here are 10 ways you could apply this principle.
1. Housekeeping. Over time, many of us accumulate a grab bag of investments—some good, some not-so-good. Those in the not-so-good category can pose a challenge. Suppose you own an expensive mutual fund.

THIS YEAR SAW THE passing of two giants of the investment world. The first was Harry Markowitz, who in the 1950s developed a concept now known as Modern Portfolio Theory. His key insight was one that today we view as so fundamental that it’s easy to take it for granted: Markowitz was the first to articulate and quantify the importance of diversification. He later won a Nobel Prize for his work.
This year also saw the passing of Charlie Munger.

WITH NO DISRESPECT TO our representatives in Congress, a new rule taking effect in January reminds me of a scene from The Jerk, an old Steve Martin movie. Playing the role of a carnival huckster, Martin shows off a wall of attractive prizes, but then narrows the choices to an impossibly small set of options.
Congress did something similar when it instituted a new rule governing 529 education savings accounts. The rule in question opens up greater flexibility in how surplus 529 funds can be used.

AS WE HEAD INTO year-end, many are cheering the financial markets’ returns. The S&P 500 has gained nearly 25% and now sits just a hair below its all-time high. Bonds are also looking more attractive, with yields at 15-year highs.
As a result, many investors are feeling a whole lot better about their portfolio balances. That’s certainly one way to measure financial progress, and it’s an important one. But as you make plans for 2024,

WITH YEAR-END IN sight, it’s a good time for some investment housekeeping. What’s worth your attention? Last week, I discussed the importance of asset allocation. According to research, this is the most significant portfolio decision you can make. But while asset allocation is important, it isn’t the only decision. Within each of the major asset classes, there’s another set of considerations.
Bonds. Earlier this year, I conducted a survey on X, as Twitter is now known,

THERE’S AN IRONY IN the world of personal finance: The activity that’s the most entertaining—picking stocks—is also, according to the data, one of the most counterproductive. Meanwhile, making asset allocation decisions is more akin to watching paint dry, and yet—according to the data—that’s one of the most important decisions an investor can make.
Asset allocation refers to the split among your investments—how much you hold in stocks, for example, versus bonds or real estate.

WHAT DRIVES THE PRICE of individual company stocks, and why do some soar while others sink? It comes down to five factors, I believe.
The first two factors are a company’s observable strengths and weaknesses. Consider Apple. Its strengths are easily quantifiable. In the U.S., it’s captured more than half the smartphone market. When you take into account the company’s premium prices, it collects a disproportionate share of the industry’s revenue. Last year, Apple’s profits hit nearly $100 billion,

WHEN THOMAS EDISON was a child, he apparently set fire to a barn on the family’s property. After it burned to the ground, his parents were furious.
“Why would you do such a thing?” his father asked.
Young Edison replied, “I wanted to see what would happen.”
The story may be apocryphal, but I was reminded of it recently when I came across a study titled “Not Learning from Others.” A group of economists wanted to understand more about how people learn.

WITH DECEMBER FAST approaching, it’s a good time to think about end-of-the-year financial planning. What steps might you take?
A popular strategy is to make charitable gifts, both to support good causes and reap a tax benefit. But before you start writing checks, take a moment to better understand your tax picture. Because of the complexity of tax forms, that’s often easier said than done. Still, you don’t need to decipher every number. Instead,

STEIN’S LAW STATES that, “If something cannot go on forever, it will stop.” It’s named for Herbert Stein, an economist who was influential in the 1970s and served as chair of the president’s Council of Economic Advisors.
Stein first made this comment when he saw government debt growing to what he felt was an unsustainable level. While half-joking in the way he put it, Stein was making a serious observation: Trends rarely last forever.

A KEY CONUNDRUM FOR investors: On the one hand, the data on tactical trading are clear. Frequent portfolio shifts are a bad idea and can damage returns. On the other hand, we shouldn’t be so wedded to the status quo that we’re unwilling to ever make a change.
With this conundrum in mind, it was notable when investor and author Howard Marks declared a “sea change” in the investment landscape and recommended that investors revamp their portfolios.

DO YOU EXPECT IT TO be warmer this winter in Minneapolis or in Miami? This isn’t meant to be a trick question. We’d probably all agree that it’ll be warmer in Miami. But what if I asked you to predict the precise temperature in either city on Jan. 1. This is a much more difficult question.
In his book Mastering the Market Cycle, investor Howard Marks uses illustrations like this to make an important point.

AN IRONY OF PERSONAL finance is that retirement can take work. More than once I’ve heard a retiree express this sentiment: “Working was easy. Retirement is complicated.”
There is, I think, a lot of truth to this. When retirement appears on the horizon, numerous questions enter the picture. There are, of course, financial concerns: “How much will I need? Do I have enough? How should I invest my savings?” These questions are important, but they aren’t the only ones.

WHAT’S THE FIRST RULE of personal finance? To answer this question, let’s look at the financial lives of two notable individuals, starting with musician MC Hammer.
When Hammer gained fame in the 1980s, he made millions. But unfortunately, his spending quickly outpaced his income. Hammer bought 19 racehorses, employed a personal staff of 200 and built a $30 million house with a 17-car garage. The result, sadly, was bankruptcy.
If MC Hammer represents one extreme of financial management,

AS THE SAYING GOES, a picture is worth a thousand words. Over the years, I’ve found certain images and illustrations to be immensely helpful in discussing investment concepts. These are the ones I’ve relied on the most:
Only in Australia. A key challenge for investors—if not the key challenge—is that none of us has a crystal ball. It’s impossible to know what markets will do next month or next year.

BACK IN THE 1980s, Michael Milken earned notoriety as “the junk bond king.” With his swagger—and his toupee—Milken was an outsized personality in a normally staid industry. But that was four decades ago. It may have been the last time that bonds were truly interesting.
On most days, bonds are about as dull a topic in finance as you can find. But here’s the challenge for investors: While bonds might be boring, they’re important—and they can be tricky.

I OUTLINED 10 REASONS everybody should have an estate plan in a 2018 article—and what was true then remains true today, especially for those whose assets could be subject to estate taxes.
Under today’s rules, the federal estate tax applies to individuals with assets over $12.9 million. That might sound like a high number. But in 2026, the limit is set to be cut in half. In addition, many states impose their own estate tax,

“YOUR CHECKING ACCOUNT balance is low.” It’s an alert none of us wants to receive, especially if we’ve just been paid. But that was the message that a friend—let’s call him Ron—got recently. A hacker had gained control of his account and started bleeding it dry.
Ron, it turns out, was lucky to have received that alert. Another friend—let’s call him Arthur—received no such alert when his account was also taken over by hackers this summer.

THE CENTRAL Intelligence Agency knows a thing or two about gathering information. That’s why a CIA publication titled The Psychology of Intelligence Analysis is, in my opinion, a valuable resource for investors.
Of particular note is a section titled, “Do You Really Need More Information?” It offers this counterintuitive finding: To make sound judgments, some amount of information is necessary. But beyond a certain point, gathering more data doesn’t always lead to better decisions.

SOMEONE ASKED ME this week if he should own pork bellies in his portfolio. While he was kidding, this does get at a real question: Should you own commodities like cattle futures, gold, oil, lumber, soybeans and more?
Those who favor investing in commodities typically cite two benefits. First, commodities are seen as a bulwark against inflation. This is obviously a timely concern. Second, because commodities don’t move in lockstep with stocks or bonds,

NO QUESTION, MANAGING an investment portfolio is tricky. On the one hand, you want stock market exposure to help drive your portfolio’s performance. But on the other, it’s agonizing when the market drops 30% or 50%—or more—as it’s done on several occasions.
How can investors strike the right balance? Like most things in personal finance, there isn’t one right answer. In general, investors can choose one of five approaches when building a portfolio.
1.

IN THE WORLD OF personal finance, there’s no shortage of formulas and frameworks for making financial decisions. But it’s also important, I think, to see these as guidelines rather than as rules. Consider the textbook view of money and happiness.
What the research says is that, all else being equal, we should opt to spend money on experiences rather than things. Let’s say the choice is between spending $1,000 on a new watch or on a weekend away.

LOOK UP THE WORD “nit” in the dictionary and you’ll find a few definitions—none of them particularly positive. Perhaps, then, it’s no surprise that the tax commonly known as NIIT can be a bit of an annoyance.
NIIT is short for net investment income tax. It originated back in 2013 to help pay for the new health care law. The net investment income tax rate is relatively innocuous at 3.8%, and it’s already been on the books for 10 years,

ON FEB. 7, 1910, AN ODD event occurred in the English town of Weymouth. A group of five arrived for a tour of HMS Dreadnought, a battleship that was the pride of Britain’s navy. The five were welcomed with fanfare, their staff having communicated in advance that they were members of the Abyssinian royal family. Their appearance was impressive: flowing robes, great jewels and turbans. Through an interpreter, the Abyssinian emperor offered military honors to the ship’s crew.

MARK ZUCKERBERG and Elon Musk have been trading barbs in recent months, going as far as discussing a “cage match”—a literal fight.
This has followed a volatile few years for their respective companies. In October of last year, Musk took over Twitter and immediately started making changes. He fired 80% of its staff, causing an uptick in technical issues, and has made other spur-of-the-moment changes to the service. This has scared away advertisers, prompting a 50% drop in revenue.

HARRY MARKOWITZ, the Nobel Prize-winning economist who passed away recently, invented a new approach to investing. Known as modern portfolio theory, it offered investors, for the first time, a logical approach to building portfolios. How much should you hold in stocks vs. bonds? Markowitz could tell you precisely.
But Markowitz also knew math wasn’t the only driver of investment decisions. In a frequently cited interview, Markowitz recalled how he decided what to hold in his own retirement plan early in his career.

NEW YORK ATTORNEY Steven Schwartz recently found himself in hot water. Schwartz was representing a passenger injured on board an Avianca Airlines flight. In a filing with the court, Schwartz cited several precedents that appeared to support his case, including Martinez v. Delta Air Lines, Zicherman v. Korean Air Lines and Varghese v. China Southern Airlines. The only problem? These cases are all fictional—made up not by Schwartz, but by ChatGPT, an artificial intelligence (AI) “chatbot.”
The judge was not pleased,

THOSE WHO LIVE VERY long lives sometimes face an unfair irony: The accomplishments of even towering figures can lose their luster over time—not because they’re proven wrong, but because the ideas they developed become so widely accepted that we forget they were once innovations. The investment world lost one such towering figure last week: the economist Harry Markowitz, who was age 95.
Markowitz first came to prominence in the early 1950s, when his PhD thesis,

IN 2014, AN INVESTOR asked Charlie Munger—Warren Buffett’s second-in-command—why he wasn’t investing in Apple. Munger responded that, “No matter what their financial statements showed,” he’d never have a high degree of confidence in the company. “It’s just too hard.”
Buffett agreed. But things changed. Today, Buffett’s Berkshire Hathaway is Apple’s third-largest shareholder, with holdings valued at more than $150 billion.
What should we conclude from Buffett’s about-face? In recent weeks, I’ve referenced studies on market timing and trading.

WHAT DO WALL STREET analysts, magazine editors, economists and academics have in common? They’ve all found it virtually impossible to make accurate market forecasts. That’s why Vanguard Group founder Jack Bogle gave this advice to investors: When markets go haywire, “Don’t do something. Just stand there.”
Warren Buffett has given the same advice. In 2008, here’s how he explained it: “In the 20th century, the United States endured two world wars and other traumatic and expensive military conflicts;

A WHILE BACK, I WAS speaking with a mutual fund manager. In describing one of his fund’s stocks, he noted, “I owned it for a while, then I sold it, but then I bought it back.” It was a surprising comment since frequent trading is, in most cases, unproductive. Indeed, Warren Buffett has often said that his preferred holding period for an investment is “forever,” and many see that long-term mindset as crucial to his success.

TODAY MARKS MY 300th weekly contribution to HumbleDollar. Over time, one key theme has emerged: While personal finance can be complicated, it doesn’t have to be. How can you simplify your financial life? Below are 10 ideas.
1. Tracking donations. In the old days, it wasn’t too difficult to track charitable gifts. You would simply refer back to your checkbook. But today, most people use debit and credit cards,

PERHAPS YOU’VE SEEN charts like the one below, which comes from Dimensional Fund Advisors. The message: Investors who try to time the market in search of better returns often end up damaging their results. To many investors, this seems intuitive, because trading isn’t easy.
But to others, market timing appears to make a lot of sense. For instance, for years, Yale University professor Robert Shiller has been maintaining a measure of market valuation known as the cyclically adjusted price-earnings (CAPE) ratio.

IN THE NETHERLANDS in 1602, the Dutch East India Company conducted the world’s first initial public offering. Then, in 1610, the Netherlands saw the issuance of the first ever stock dividend. And in 1611, when the Amsterdam Exchange opened, the Netherlands became home to the world’s first stock market. Throughout the 1600s, the Netherlands continued to see further financial growth and innovation.
During that period, the Dutch economy was among the world’s largest. But its dominance faded over time,

LOOK AT THE STOCK market, and you’ll see that certain stocks often do better than others. Technology shares have been standout performers over the past 10 years, and health care stocks have done very well.
But research has also found that certain types of stocks have done better than others. Smaller-company stocks, for example, have outpaced those of larger firms. In the academic literature, characteristics like this, which are correlated with outperformance,

SUPPOSE YOU WERE presented with two prospective investments. On the surface, they look similar, except one has outperformed the other in 12 of the past 15 years. Which one would you choose?
This example isn’t hypothetical. The two investments in question are the S&P 500 and the EAFE Index. The S&P 500 is broadly representative of the U.S. stock market, while EAFE stands for Europe, Australasia and Far East. It’s the most commonly referenced index for developed international stock markets.

WHERE DOES THE STOCK market stand? After 2022’s decline, is it now fairly valued—or still overvalued?
When I think about questions like this, I’m reminded of an opinion piece written by Robert Shiller a few years back. By way of background, Shiller is a professor at Yale University and a Nobel Prize recipient. Along with a colleague, he created one of the more well-known and well-regarded measures of market valuation: the cyclically adjusted price-earnings ratio (CAPE).

A FEW YEARS BACK, I related a story about the comedian Joan Rivers. Her daughter, Melissa, likes to joke that her mother was always very consistent. Wherever she was, she would always drive at 40 miles per hour, whether it was on the highway, in a school zone or in the driveway.
This is funny, but it also illustrates a key challenge for investors. On the one hand, it’s important to be consistent. But at the same time,

NETFLIX BEGAN AN experiment in 2003 that seemed crazy to management experts. It instituted a policy of unlimited vacation time for its employees. In the years since, a number of other companies have followed Netflix’s lead, offering employees unlimited paid time off.

The results have run counter to intuition: Employees who are offered unlimited vacation end up taking less time off than those working for companies with traditional vacation policies. Why? A common explanation is that people struggle when they lack clear guidelines.

OPEN A FINANCE textbook, and you’ll find discussions of volatility and beta, value-at-risk, the Sharpe ratio, the Sortino ratio, the Treynor ratio and many other quantitative tools for measuring risk. But what should you make of these metrics? Are they an effective way to control risk in your portfolio?
These tools do have decades of research behind them, and they can be useful. But I believe they’re also incomplete. Worse yet, they can be misleading.

IN THE WEEKS SINCE Silicon Valley Bank (SVB) disintegrated, there’s been a fair amount of post-mortem analysis. In the end, two factors drove the bank’s demise.
First, SVB’s customer base was concentrated among venture capital-backed technology companies. Because of that, nearly 90% of deposits topped the FDIC threshold and were thus uninsured.
Second, owing to 2022’s rise in interest rates, SVB’s bond portfolio took a hit. That sparked concern about the bank’s solvency, prompting depositors to overwhelm the bank with withdrawal requests.

I SPOKE RECENTLY with a fellow who had climbed Mount Everest. The first question I asked: What was it like at the top?
What I expected him to say was that the view was dramatic. Instead, he said, his time at the summit turned out to be less than he’d expected. For starters, it was 4:45 a.m., so there wasn’t a lot of visibility. In addition, it was minus 45 degrees. Because of that,

IN THE WEEK SINCE Silicon Valley Bank (SVB) failed, a debate has raged: Did the government do the right thing when it decided to guarantee all of SVB’s depositors, including those that exceeded FDIC limits?
On one side of this debate are those who view the government’s action as an inappropriate and undeserved bailout. In an article titled “You Should Be Outraged About Silicon Valley Bank,” The Atlantic argued that the bank’s failure was the predictable result of incompetent risk management.

THERE’S SOMETHING ODD going on in the housing market. Mortgage rates are appreciably higher than they were a year ago, but home prices—on average—have yet to fall. As of the most recent reading, prices continue to rise on a year-over-year basis. It reminds me of the cartoon character Wile E. Coyote, who experiences a delayed reaction every time he runs off the edge of a cliff. It’s only after he looks down that he realizes he has a problem.

“HOW MUCH CAN I withdraw from my portfolio each year?” It’s one of the most common questions that retirees ask.
In the past, I’ve talked about the 4% rule, a popular tool for addressing this question. Among the reasons it’s so popular is its simplicity: In the first year of retirement, a retiree withdraws 4% of his or her portfolio, and then that amount increases each year with inflation. If you have a $1 million portfolio,

IN FORT LAUDERDALE, an unusual property sits wedged in among a row of waterfront mansions. It’s a 35-acre patch of wooded wilderness with just a single home, called Bonnet House. It was for many decades the winter residence of a woman named Evelyn Bartlett.
She first began spending winters at Bonnet House in the 1930s, and she continued to live there following her husband’s death in the 1950s. By the 1980s, however, the property’s assessed value had reached $30 million,

I’VE OFTEN COMPARED the stock market to a Rorschach test. Depending on your perspective, what’s happening can look very different. But even in a market full of Rorschach tests, one company’s stock stands out: Tesla. Some people see it as a world-class company that’s changing the world. Others see it as a company led by an erratic genius that one day will inevitably fade—like MySpace or Polaroid.
Recently, a blogger named Alex Voigt wrote that Tesla’s head start in electric vehicles “will soon make Toyota look like what it is—a loser.” He then added for emphasis: “Dead man walking.”
Is Voigt right or wrong?

IN THE WANING DAYS of 2019, Congress passed the SECURE Act, a law that delivered a mixed bag of changes for retirement savers. Well, Congress has been busy again. At the tail end of 2022, a follow-up law—known as SECURE 2.0—was signed into law.
The good news: There’s a whole lot included in this new law. The bad news? There’s a whole lot included in this new law. SECURE 2.0 presents a number of new planning opportunities but,

IT’S HUMAN NATURE to be impressed by things that sound sophisticated or seem complex. In the world of personal finance, this certainly applies to the planning tool known as Monte Carlo analysis.
Its roots go back to the 1940s, when it was developed by Stanislaw Ulam, a physicist working on the Manhattan Project. Today, it’s a popular way to assess the strength of a proposed retirement plan. If you’ve seen presentations indicating that a financial plan has a particular probability of success,

ONE WINTER DAY IN 2016, I jotted down a few comments about the financial markets and emailed them to a group of clients. I received a few responses—some of them positive—so I did the same thing the following week, and I’ve continued that practice every week since.
For better or worse, when it comes to investment markets, there’s always something new to discuss. But it can also be helpful to pause and revisit key investment principles from time to time.

IS THE STOCK MARKET headed for a sea change? That’s the argument money manager and author Howard Marks makes in his most recent memo.
The sea change Marks is referring to: For four decades, the federal funds rate declined steadily—from a peak of 20% in 1980 to 0% in 2020. The result, Marks argues, was a steady tailwind for the stock market.
In January 1980, the S&P 500 index stood at 108. At its peak early last year,

LAST WEEK, I TALKED about Carveth Read, the English philosopher who’s famous for saying, “It is better to be vaguely right than exactly wrong.” This, in my view, is one of the most important ideas in personal finance.
My focus last week was on the “vaguely right” part of Read’s statement. But what about the second part—the importance of not being “exactly wrong”? Below are seven situations in which trying to be exactly right might,

ONE OF THE MOST important ideas in personal finance comes not from a financial expert but from a 20th century English philosopher named Carveth Read. “It is better to be vaguely right,” he wrote, “than exactly wrong.”
Why is this idea important? It gets to the heart of why financial planning can be so tricky. For starters, few people—if any—can claim to be perfectly rational when it comes to money decisions. But more to the point,

I’M NOT BIG ON MAKING New Year’s resolutions. Still, January is a good time to conduct some financial housekeeping. Below are 10 ideas to consider as the calendar turns over.
1. Portfolio cleanup. I sometimes feel like a broken record when I talk about the disadvantages of actively managed mutual funds. Among other issues, they tend to underperform and are tax-inefficient. But here’s the challenge: Even after factoring in 2022’s decline, the S&P 500 has risen more than 600% since 2009’s market bottom.

IN THE INVESTMENT world, every year is unique. This year certainly has been.
But in some ways, every year is also the same. The specific events change, but many of the underlying themes and challenges don’t change a whole lot. As 2022 winds down, it’s a good time to take a closer look at six of those themes, as well as the steps investors might take to navigate them when, invariably, they present themselves again in 2023.

IN BEHAVIORAL FINANCE, there’s an important concept that doesn’t get a lot of attention: It’s called temporal discounting. The idea is that we view our current and future selves, to some degree, as different people—and there’s a tendency to discount the needs of the “other” person. It’s an interesting idea because, even for the most diligent planners and savers, there’s an inherent tension between the financial needs of today and those of tomorrow.

Take the “latte factor,” which argues that a young person could accumulate nearly $1 million in savings simply by forgoing a daily coffee and muffin.

IN A TYPICAL YEAR, the bond market doesn’t attract much interest. That’s by design. The role of bonds in a portfolio is to serve as a bulwark against the unpredictability of stocks. They’re supposed to be boring.

All that changed this year. Thanks to rising interest rates, the most common total bond market index, the Bloomberg Aggregate, has lost about 11%. To put that in perspective, this index has delivered a negative return in only three of the past 25 years.

PERSONAL FINANCE books don’t exactly rank as the most sought-after holiday gifts. Still, if there’s a money nerd in your life—or someone who aspires to be one—below are 10 personal finance book recommendations.
Why Does the Stock Market Go Up? by Brian Feroldi. This book seeks to answer 60 of the most commonly asked questions in personal finance. In so doing, it demystifies many of the concepts, terms and acronyms that we often ​hear but may not fully understand.

WHEN ROSS PEROT RAN for president in 1992, a pillar of his campaign was tax reform. Federal tax rules, he pointed out, had grown to more than 80,000 pages. His proposal: Start over and replace everything with a simple flat tax.

Perot’s campaign for tax reform didn’t make much progress, but many can sympathize with his frustration. Because of the complexity of tax rules, financial planning often ends up feeling like the children’s game Operation—with penalties for even the slightest misstep and confusion around every corner.

A UNIVERSAL TRUTH about market bubbles is that they’re​ masters of disguise. Each new bubble appears different enough, at least on the surface, to reel in unsuspecting investors. While bubbles are almost as old as the market itself, the latest example—centered around the cryptocurrency exchange FTX—is particularly impressive. At this point, no one is 100% sure what happened, but this is what we know so far.
Back in 2017, a 25-year-old MIT graduate named Sam Bankman-Fried started a hedge fund to trade cryptocurrencies.

THERE ARE USUALLY TWO answers to every personal-finance question: There’s what the calculator says—and then there’s how you feel about it. What does that mean in practice? Let’s look at an example.

Suppose you’re considering when to claim Social Security. Many retirees struggle with this question. On the one hand, the government offers a strong incentive to wait: For each year you forgo Social Security—up to age 70—your future benefit will grow by some 8%.

I DON’T ENVY THE FOLKS in Washington. Last year, many accused Federal Reserve policymakers of being asleep at the wheel as they downplayed the risk of rising inflation. This year, of course, it’s been the opposite: The Fed has been in overdrive, raising interest rates aggressively. So far, the Fed has pushed through six increases in a row, totaling 3.75 percentage points. Many are now criticizing the Fed for moving too quickly.
This is in contrast to the challenge the Fed had been dealing with before COVID.

I’VE TALKED IN EARLIER articles about asset-liability matching. It’s ​a concept popular with insurance companies to manage investment risk. It’s a very formal approach and not one I would expect an individual investor to follow too literally. But it’s a notion that, in general, can help individuals make asset allocation decisions.
In his book, The Outsiders, William Thorndike highlights another well-known principle in corporate finance that can also be applied to personal finance: It’s called capital allocation.

WHEN I WAS IN SCHOOL, corporate executives often visited for guest lectures. Two of these presentations still stand out in my mind.
The first was the CEO of a company then called Flextronics—now simply Flex. It’s a contract manufacturer that assembles products for other companies. Apple, for example, doesn’t have factories of its own and instead relies on outsourcers like Flex to build its products, usually in Asia.
You might wonder why a presentation like this would be memorable.

WARREN BUFFETT HAS said that, when he’s in his office, he spends about 80% of his time reading—​as much as 500 pages each week. And for good reason. One of his mottos is that “knowledge compounds.”

Judging by his track record, this approach seems to work. Even in his 90s, Buffett believes there’s always more to learn and that more knowledge will lead to better investment results.

At the same time, investors often invoke expressions that suggest otherwise: No one has a crystal ball.

FOR ELON MUSK, IT HAS—to use his own words—been a “very intense seven days.” Just over a week ago, Tesla demonstrated a new prototype product, a robot called Optimus. A week ago, it announced that it had delivered a record number of new vehicles in the third quarter. And, on Wednesday, a rocket built by SpaceX, one of Musk’s other companies, completed a successful launch from Cape Canaveral, carrying astronauts to the International Space Station.

A FAVORITE QUOTE in the world of personal finance comes from Ernest Hemingway’s 1926 novel The Sun Also Rises.
“How did you go bankrupt?” Bill asked.
“Two ways,” Mike said. “Gradually, then suddenly.”
Money troubles are a common theme throughout literature. Charles Dickens probably summed it up best. In David Copperfield, a fellow named Micawber laments: “Annual income twenty pounds, annual expenditure nineteen six, result happiness. Annual income twenty pounds,

INFLATION THIS YEAR has been running at more than four times the Federal Reserve’s target of 2%, forcing the central bank to raise interest rates multiple times. As a result, both the stock market and the bond market have been struggling. This has investors searching for alternatives.

At the top of the list for many people is gold, which gained a reputation as a bulwark against inflation in the 1970s. During that decade, when inflation was running hot,

INSURANCE COMPANIES are disproportionately represented among the world’s oldest companies. John Hancock was founded in the 1860s. Cigna dates to the 1700s. Some insurers are even older. Why is that?

In my opinion, it’s because they employ a strategy called asset-liability matching. In simple terms, insurers organize their finances so cash is always available when they need it.

Let’s say each winter typically results in $100 million of auto claims for a particular insurer.

JAMES J. CHOI is a finance professor at Yale University. But in a recent paper titled “Popular Personal Financial Advice versus the Professors,” Choi played the role of (somewhat) neutral arbiter. The question he sought to answer: Do popular—that is, non-academic—personal finance books offer advice consistent with the academic literature? And if not, is that a problem?

To conduct his study, Choi looked at 50 personal finance titles including The Millionaire Next Door, 

YOU MAY BE FAMILIAR with the term ESG. This is an investment approach that—in addition to traditional financial metrics—also weighs environmental, social and corporate governance considerations when picking investments.
ESG isn’t new, but it’s stirred up a fair amount of controversy recently. As an investor, it’s worth understanding what the debate is about and how you might navigate it.
ESG has been around for years, but its popularity has recently hit an inflection point.

EXCHANGE-TRADED funds are popular, but their complex structure makes them difficult to understand. A question I hear frequently: Are exchange-traded funds (ETFs) more tax-efficient than traditional mutual funds?
The evidence suggests they are. One recent study found that ETFs distribute capital gains to shareholders much less frequently than traditional mutual funds and, when they do, those gains are smaller. It’s worth understanding why that’s the case.
Let’s first look at the mechanics of a traditional mutual fund.

I GOT AN ANGUISHED call from an investor last week. Let’s call her Emily. Emily’s accountant was finishing up her tax return and was surprised to see a $113,000 capital gain. The explanation turned out to be just as surprising.
The issue stemmed from a well-intentioned move by Vanguard Group. In late 2020, the firm announced it was broadening access to a set of lower-cost mutual fund share classes.
Mutual fund share classes are like fare classes on an airplane.

THE ENGLISH POET Alfred Tennyson wrote that it is “better to have loved and lost than to have never loved at all.” When it comes to matters of the heart, maybe Tennyson was right. But when it comes to personal finance, I’m not sure that’s the case. If you’ve ever seen a gain slip through your fingers, you know the feeling of regret can be powerful.
Two conversations last week prompted me to take a closer look at this topic.

AT THE MUTUAL FUND company where I once worked, the stock and bond teams liked to poke fun at one another. Bond managers viewed the stock-pickers as overpaid storytellers. Meanwhile, the stock-pickers saw the world of bonds as stultifying. “Playing for nickels and dimes” is how one of them put it.
For better or worse, bonds do indeed represent the slow lane. But this year, with bond prices depressed by rising interest rates, investors are wanting to learn more.

THE MEGA MILLIONS drawing on Friday was worth more than $1 billion. Would you be happy if you’d been the lucky winner?
Last week, I talked about the Vanderbilts. Once the wealthiest family in America, they saw their fortune dwindle because of aggressive spending. Back in the 1890s, for example, the family spent $7 million building the Breakers, a summer home in Newport, Rhode Island. That’s the equivalent of $220 million today. When it was completed,

WHEN HE DIED IN 1877, Cornelius “Commodore” Vanderbilt was by far the wealthiest American, with a fortune of $100 million. In the 10 years after his death, his son William succeeded in further doubling those assets. It was an astonishing level of wealth. But that’s precisely when things began to turn.
One of Cornelius’s grandsons built the 125,000-square-foot Breakers mansion in Newport. Another commissioned Biltmore in North Carolina, which is still the largest home in America.

I RECEIVED A CALL last week from a college student who’d started a successful business. His school, he said, didn’t offer any practical courses in personal finance, so he asked my advice on investing.
We walked through nine key questions. I would offer the same advice to investors of any age.
1. Why should I expect stocks to go up? One way to answer this question would be to invoke the oft-quoted phrase that “history doesn’t repeat itself but it often rhymes.” Stocks have delivered roughly 10% returns per year since reliable recordkeeping began in the 1920s.

U.S. STOCKS ARE DOWN almost 19% so far this year. The broad bond market, surprisingly, has also lost money, sliding almost 11%.

At times like this—when the headlines are almost all negative—the standard advice is to avoid panicking and stay focused on the long term. I agree with that, and indeed the data are clear: Investors who attempt to time the market with “tactical” trades often suffer whipsaw. But that doesn’t mean we should bury our heads in the sand.

A FEW WEEKS BACK, I mentioned Robert Shiller’s book Narrative Economics. His contention: Stories—to a surprising degree—often drive markets.
Similarly, the investment world is driven by a good number of sayings and aphorisms. Many of these are entertaining. Some are even useful. But they can also be tricky. Any time advice is delivered in a pithy phrase, it seems to carry extra credibility—as if it were a truth handed down from above.

I ARGUED LAST WEEK that bitcoin wasn’t a great investment. The reality: Only a minority of investors hold cryptocurrencies, which is a good thing, in my opinion. But there are, alas, many other ways to get off track when building a portfolio.

In fact, if I ever wrote an investment book, it might be in the style of Dr. Seuss and titled Oh, the Investments I’ve Seen. Want to build a sensible portfolio and avoid common pitfalls?

SINCE THE START OF the year, the stock market has dropped almost 24%. That’s significant, but it pales next to the losses suffered by cryptocurrency investors, with the shellacking continuing into this weekend.
Dogecoin is down more than 90%, and smaller currencies like terra have lost essentially all their value. Even bitcoin and ethereum, which are much more established, have suffered big losses. Ethereum is down around 75% year-to-date, and bitcoin has fallen some 60%.

ROBERT SHILLER, in his book Narrative Economics, argues that stories can be a powerful force in moving markets—more so even than facts or data. Recently, I gained a better understanding of why that’s the case.

I was speaking with a fellow and, it seemed, we disagreed on nearly every topic. But the way he presented his arguments made them sound surprisingly persuasive. What I realized is that, in the world of finance,

THE INVESTMENT consulting firm Callan publishes its periodic table of investment returns each year. It shows the results of key asset classes on a year-by-year basis. Each asset class is color-coded and ranked from best to worst. This makes it easy to see not just annual performance, but also relative results.

The periodic table is valuable because it illustrates that there’s rarely a consistent pattern to relative returns from one year to the next.

A FEW WEEKS BACK, I discussed the notion of “the four horsemen of the investor apocalypse.” A concept proposed by Morningstar Managing Director Don Phillips, these are the factors that—in his experience—tend to lead investors off course. But what about success? What are the factors that contribute to success for investors?
“Investing,” says legendary investor Warren Buffett, “is not a game where the guy with the 160 IQ beats the guy with a 130 IQ… You need to be smart,

IF YOU’VE TRIED TO buy a car or a home recently—or have even just been to the grocery store—I’m sure you’re aware how much prices have jumped over the past year. John Taylor certainly has an opinion on the topic.

Taylor is an economics professor at Stanford University. While not a household name, he’s a leader in economic circles. Before Jerome Powell was appointed Federal Reserve chair in 2018, Taylor was a candidate for that spot.

DON PHILLIPS is a former CEO of the research firm Morningstar. In a recent commentary, Phillips discussed what he called the “four horsemen of the investor apocalypse.” I hasten to add that Phillips isn’t predicting any kind of apocalypse. Rather, he wanted to highlight factors that can cause problems for investors. Phillips’s four horsemen are complexity, concentration, leverage and illiquidity. It’s worth taking a closer look at each, especially amid today’s rocky financial markets.

A FRUSTRATING reality: Uncertainty is always a factor in personal finance. Still, some aspects are somewhat predictable. Among them is the connection between interest rates and other parts of the economy. Consider four key relationships:

1. Interest rates and inflation. Inflation has been the financial topic of the year. The Federal Reserve has hiked interest rates twice so far in 2022, including a larger-than-average increase last week, as it tries to rein in rising prices.

IN A NOTE TO CLIENTS last week, Deutsche Bank analysts wrote that they expect a “major recession.” What should you make of ominous predictions like this?

First, don’t panic. Yes, Deutsche Bank is a big institution. But it’s worth noting that last week two equally prominent institutions also weighed in—with a different point of view. Goldman Sachs argued that a recession is “not inevitable.” UBS wrote that, “We do not expect a recession.” They can’t all be right.

WHEN IT COMES to estate planning, folks with taxable estates—that is, with assets in excess of $12 million—tend to fall into one of two camps. The first recognize that their estates will have to hand the IRS 40 cents out of every dollar above that $12 million threshold. They also know that this limit is scheduled to be cut in half in 2026 and could be even lower in the future. As a result,

MANY FINANCIAL questions have clear answers. Does it make sense to engage in day trading? Probably not. Should you invest everything in bitcoin? I wouldn’t recommend it. Is it smart to carry a big credit card balance? It’s hard to think of a good reason.

Many other financial questions, though, might seem to have clear answers. But upon closer examination, they actually fall into the “it depends” category. Below are six such questions:

1.

AS I NOTED LAST WEEK, investing can be maddening. But it isn’t just investing. Many other personal-finance questions can also drive us crazy. Why is that?

One reason: The stakes are often high, so mistakes can be costly. A second reason: By definition, all data are historical, but all decisions are about the future. To the extent that the future doesn’t look like the past, we have a problem.

Those two factors are very real.

INVESTING CAN BE maddening. Stocks that look like they’re going up can end up falling, while investments that look like they’re headed for the dustbin can suddenly bounce back. This leaves investors in a difficult position—because the right thing to do often feels wrong.
Investing requires us, quite often, to act contrary to our own intuition. Here are four examples.
1. Don’t equate price with quality. When consumers walk into a retail store,

AS YOU MIGHT GUESS, my favorite Seinfeld episode is “The Stock Tip.” It starts with a conversation between George and Jerry.

“My friend Simons knows this guy Wilkenson,” George says. “He made a fortune in the stock market. Now he’s got this new thing.” George goes on to explain that Wilkenson has millions invested in a company called Centrax.

He urges Jerry to invest along with him, though the details are thin.

ARISTOTLE WROTE THAT, “It is a part of probability that many improbable things will happen.” Investors certainly understand this. For better or worse, we know that the market has frequent ups and downs. On average, the S&P 500 has dropped 10% or more approximately every 18 months, and it’s dropped more than 20% about every four years.
Unfortunately for investors, another fundamental truism also applies: We dislike losses disproportionately more than we like gains.

“MARGIN OF SAFETY” is a concept with deep roots in finance, going back at least as far as Benjamin Graham’s Security Analysis, first published in 1934. The idea: Investors should never be too confident in any analysis and should leave the door open to the possibility that their analysis might be right but not precisely right.
Suppose you’re interested in buying Microsoft stock. And suppose that, after analyzing it,

I REALLY WISH THERE was a topic to discuss today other than the grotesque war being perpetrated against Ukraine. But unfortunately, there isn’t. This situation has prompted numerous questions from investors. Below are the three questions I’ve heard most over the past week.

1. What’s the financial impact of these events? Since Russia invaded Ukraine, global stock markets have bounced around with no discernable pattern (other than the Russian market, which has—not surprisingly—been a disaster).

I WROTE ABOUT the perils of timing the market last Sunday. This week, I’ll address its close cousin: stock-picking.
These days, many people accept that stock-picking isn’t a great idea. Evidence shows that both professional and individual investors fare poorly, on average, when they choose individual stocks. But why exactly is that? How is it that indexes—which are simply lists of stocks—so frequently outpace the results of professional portfolio managers?
There’s more than one answer to this question.

SOMEONE ASKED ME last week about a popular and frequently cited market statistic. It goes like this: The U.S. stock market has historically delivered an average annual return of 10%. But if an investor had missed just the five best days over the past 30 years, that return would have been cut to 8.6%. If the investor had missed the 15 best days, the return would have been reduced even further, to 6.5%. Missing the best 25 days out of that 30-year period would have chopped an investor’s return in half—to just 4.9%.

HARRY MARKOWITZ WAS a graduate student in economics at the University of Chicago. It was 1954, and he had just finished defending his thesis. Most of the committee accepted his work. But Milton Friedman, an economist with a national reputation and easily the most influential member of the economics faculty, had a problem. While he found no errors in Markowitz’s work, the problem was that it contained no economics. Markowitz’s thesis was about investments and,

I’D LIKE TO START with a seemingly simple question: If you purchased an investment for $19,000 and later sold it for $287,000, would there be a gain or a loss? If you answered that there would be a gain, I’d agree with you. Specifically, it appears the gain would be $268,000. But what if there was no gain and the investment was actually sold at a loss? Could that be the case?

DOES IT MAKE SENSE to heed the advice of experts? This doesn’t seem like a hard question. I certainly listen to my doctor and to many others with specialized expertise. As a society, we all rely on experts—from civil engineers to airline pilots to firefighters—for our health and safety.
At the same time, however, human judgment seems to be riddled with flaws. Consider these examples:

After reading his senior thesis, Michael Lewis’s advisor at Princeton University gave him this advice: Whatever you do,

I DESCRIBED A SET of ideas last year that I called truisms of financial planning. They’re concepts I’ve found helpful in navigating the world of personal finance. Below are seven more.

1. Jeff Bezos is a bad role model. So are Bill Gates, Elon Musk and pretty much every other billionaire. Of course, they’re all great geniuses, so why would I say that? The problem is how they made their money. In each case,

I’LL ACKNOWLEDGE THAT today’s topic isn’t the most upbeat. I want to talk about risk—and, specifically, some of the underappreciated risks related to retirement.

In thinking about risk, the hardest part—in my view—is that it defies a single definition. Because of that, there’s no uniform yardstick for measuring it and thus no single strategy for managing it. As Howard Marks states in his book The Most Important Thing, “Much of risk is subjective,

JUST HOURS INTO the new year, I received an email from a concerned investor. His worry: the state of the market—the S&P 500, in particular. With hundreds of constituent companies, the S&P index has the veneer of broad diversification. But scratch the surface, and it seems to carry more risk than investors might like. The issue: It’s top heavy.

As a group, the top 10 companies in the S&P 500 account for more than 30% of its overall value.

LOOKING BACK OVER the past two years, one word comes to mind: extreme. It’s been a period of extremes in the market and the economy. Many have benefitted, but we’ve also seen excesses that aren’t necessarily healthy—from the rise in NFTs to the craze in SPACs to the boom in day trading. That’s why, as you look ahead to the coming year, the theme I recommend is moderation.

LAST WEEK, I REFERRED to the stock market as a hall of mirrors. That was perhaps too kind. With its erratic and often illogical movements, the market also has elements of a pinball machine, a rollercoaster and maybe a clown car. This has always been the case, but it feels especially true this year. There’s one silver lining, though. The market’s recent behavior highlights many of the behavioral biases we read about in textbooks.

LAST WEDNESDAY, the Federal Reserve’s policymaking committee concluded its quarterly meeting with two big announcements. First, the Fed is going to scale back its monthly purchases of Treasury securities. Because these multi-billion-dollar purchases have helped keep interest rates low, the Fed’s objective here is to let interest rates begin to rise. That was the first announcement.

The second is that the committee expects to raise its benchmark rate by nearly a full percentage point next year.

GOT CHARITABLE giving on your mind? Join the crowd. Many folks donate at this time of year, with their charitable giving driven by the charities themselves.

As solicitations arrive, people decide on a case-by-case basis whether to pull out their checkbooks. But some folks follow a more structured process, and that’s the approach I favor. It includes asking these three questions:

1. How much ideally would you like to give? As a starting point,

THE STOCK MARKET’S recent wrenching price swings offer a valuable investment lesson. Let’s start by reviewing the facts:

On the day after Thanksgiving, the S&P 500 suffered its worst day in months and the Dow had its worst day in more than a year. The proximate cause: news about Omicron, a new coronavirus variant. Overnight, investors seemed to revive their playbook from the early 2020 recession. Airline stocks dropped precipitously. Oil plunged 13%. Meanwhile,

RON LIEBER, in his book The Opposite of Spoiled, describes a 2012 conversation between Chris Rock and Jon Stewart. In an interview on Stewart’s show, they got around to discussing the challenges both faced in raising children who could remain grounded amid wealthy surroundings.

Rock described how his own modest upbringing differed from the comfortable life his children enjoy. “My kids are rich,” he said. “I have nothing in common with them.”

Stewart agreed.

A FRIEND DESCRIBED his recent experience trying to buy a new car. “I had two choices,” he said. “One dealer wanted full sticker price. The other wanted even more. It wasn’t much of a choice.”

The inflation situation in the car market is well understood. A shortage of components is limiting car makers’ output, driving up prices. But inflationary pressures aren’t limited to cars. The most recent reading for the Consumer Price Index was higher than it’s been in 30 years.

LIFE IS EXPENSIVE—especially for young adults contending with budget busters like housing and tuition. If you have adult children facing these expenses and want to help them financially, you may be wondering what’s the best approach. While every family is different, below are three principles that I’ve seen work well.

1. Transparency. This applies in several ways. First, you should let your children know your objectives for these gifts. Do you want to see them spend it on something specific—such as a home down payment—or are they free to use it as they see fit?

WALL STREET JOURNAL personal finance columnist Jason Zweig recently made this observation: Getting rich isn’t the hard part, he said. “Staying rich is the hard part.”

On the surface, staying rich might seem easy. After all, you simply need to build a balanced portfolio and then withdraw from it at a reasonable rate. Sure, there are stories about lottery winners and professional athletes going broke. But you might assume that phenomenon—having a hard time staying rich—is limited to such extreme cases.

A FEW WEEKS BACK, I talked about the good-is-better-than-perfect principle. A close corollary: Approach financial decisions incrementally. What do I mean by that? An example is dollar-cost averaging, where you invest a sum of money in regular increments, rather than all at once.

Does dollar-cost averaging guarantee a better outcome? No. But it takes what would be one big decision and breaks it into several smaller ones. The benefit: Each of those smaller decisions ends up carrying lower stakes.

BACK IN THE 1950s, economists Franco Modigliani and Merton Miller developed a theory that, even today, is taught in virtually every finance class.

To understand the theory, suppose you’re running a company and want to build a new factory. To raise money for the project, you generally have two options: You can sell shares to investors or you can borrow money. No one disputes that basic framework, but Modigliani and Miller added a twist: They argued that,

I RECENTLY STARTED reading Think Again, the new book by Adam Grant. Subtitled The Power of Knowing What You Don’t Know, Grant’s book got me thinking about all the ways that, over the years, conversations with clients have led me to look at things through different lenses. Below are eight such topics:

1. There’s one important financial question that stumps most everyone—for good reason. In building a financial plan,

EARLIER THIS MONTH, The Wall Street Journal carried a seemingly innocuous article by Derek Horstmeyer, a finance professor at George Mason University. Horstmeyer described an analysis he and his research assistant had recently conducted. The question they sought to answer: Could investors achieve better results in their 401(k)s by avoiding target-date funds and instead constructing their own portfolios?

If you aren’t familiar with them, target-date funds are intended as all-in-one solutions for investors.

FINANCIAL PLANNING is, for the most part, straightforward. You want to save enough for the future and then avoid a shortfall by investing those savings wisely. Pretty much every other topic in the world of personal finance—from asset allocation to paying taxes to safe withdrawal rates—can be viewed through the lens of those two overall goals.
But there’s one topic that isn’t straightforward at all, and that’s philanthropy. It’s not straightforward because it runs counter to those two fundamental goals.

OPEN AN ECONOMICS textbook, and you’ll find this fundamental principle: When the money supply expands—that is, when the government prints more money—higher inflation is often the result. This topic has, for good reason, been on investors’ minds lately. Since the pandemic began, the Federal Reserve has increased the money supply by several trillion dollars.

Is higher inflation inevitable? I see five possible answers to this question:

1. Yes, of course. Between 2010 and 2020,

I RECENTLY LEARNED that crooks like to use tungsten to defraud gold investors. Here’s how it works: Gold bars are typically validated by weight. If a standard size bar clocks in at the expected weight, it’s assumed to be pure. But tungsten, it turns out, has a very similar density to gold. Crooks will drill out a bar’s core, fill it with tungsten and then cover their tracks by applying a thin veneer of gold.

PERSONAL FINANCE pundits love to debate safe withdrawal rates—the amount a retiree can withdraw each year from a portfolio without depleting it too quickly. I agree this is an important topic. In fact, I’ve addressed it a few times myself in recent months.

In July, I discussed the well-known 4% rule. A few weeks ago, I described an alternative called the bucket strategy. But as you build your retirement plan, withdrawal rates shouldn’t be the only consideration.

I HAVE A RELATIVE—let’s call her Jane. Last year, in the early days of the pandemic, Jane had the foresight to buy shares in vaccine maker Moderna. With the benefit of hindsight, it was a smart decision.
But it wasn’t a difficult one, in Jane’s view. It was no secret that the company was working on a COVID-19 vaccine. It was also clear that vaccines would be in high demand. That made the investment case clear.

THE MUCH-DEBATED 4% rule—which I wrote about back in July—is a popular way to think about portfolio withdrawals in retirement. But it isn’t the only way. Another approach, called the bucket system, is also worth understanding. Below is some background.
What is the bucket system? As its name suggests, an investor divides his or her portfolio into multiple containers. Each container, or bucket, is then assigned a different role.
The most popular implementation of the bucket system involves three containers: The first is earmarked for a year or two of spending and is held entirely in cash.

A WHILE BACK, I assembled two personal finance reading lists—what I called 101 and 201 level titles. But time doesn’t stand still. Below is a list of newer books, along with a few classics that didn’t fit on the earlier lists. They’re organized into three categories: retirement planning, investing and behavioral finance.
Retirement Planning

Can I Retire? by Mike Piper. There’s no shortage of retirement books. But if you want a straightforward guide that covers the most critical topics in an easy-to-read format,

I’VE NEVER BEEN a fan of financial planning rules of thumb. To understand why, consider a common shortcut for choosing an asset allocation: The allocation to bonds in a portfolio, according to this rule of thumb, should equal an investor’s age.

For example, if an investor is 65 years old, his or her allocation to bonds should be 65%. That sounds reasonable—until you realize that Microsoft founder Bill Gates is 65. Should he have the same asset allocation as everyone else his age?

TODAY’S STOCK MARKET reminds me of Charles Dickens’s famous line: “It was the best of times, it was the worst of times….”
It’s the best of times, of course, because the market continues to hit new highs. From a low of 2,237 in March 2020, the S&P 500 has doubled. Over the 10 years through July, the S&P has delivered an average annual return of 15.4%, including dividends, far above the historical average of 10%.

THE 19TH CENTURY feud between the Hatfields and the McCoys doesn’t hold a candle to the debate between supporters of index funds and supporters of active management.
Those in the index fund camp cite decades of data—going back to the 1930s—to support their view that active management is a fool’s errand. In fact, Standard & Poor’s regularly publishes a study it calls SPIVA, short for S&P Index Versus Active. Each time, analysts there reach the same conclusion—that it’s exceedingly difficult for an actively managed fund to beat its benchmark.

ON THE SURFACE, Social Security seems straightforward: During our working years, we pay into the system. Then, when we’re older, the government sends a check every month for life.
But scratch the surface and you’ll find that Social Security offers a number of additional benefits. Among them: a benefit for spouses. This can be highly valuable, but the rules around it are complex and very specific. Consider, for example, the late talk show host Johnny Carson.

THE 4% RULE IS ONE of the best-known ideas in personal finance. But is it really a rule? And does it apply to you?

Let’s start at the beginning. The father of the 4% rule is a financial planner named William Bengen. Back in the early 1990s, he became frustrated with the prevailing rules of thumb for retirement planning. He found them too informal and set out to develop a more rigorous approach. The question he sought to answer: What percentage of a portfolio could a retiree safely withdraw each year?

IF THERE’S ONE STORY that seems to have captured the investing public’s imagination this summer, it’s the revelation that venture capitalist Peter Thiel has managed to accumulate more than $5 billion in his Roth IRA—where it will be entirely tax-free to him.

In its reporting, ProPublica, the news outlet that carried the story, focused mostly on the tax aspects—the fact that Thiel was able to use his Roth IRA in such unusual ways. In my opinion,

A FEW WEEKS BACK, I discussed some of the challenges with traditional long-term-care (LTC) insurance: In addition to steep and rising premiums, these policies are complex. Many policyholders have to contend with an annual renewal letter that presents a mind-numbing matrix of options.
But there’s more to it than that. Long-term care is also an emotional topic. There’s the expression that personal finance is more personal than it is finance. I’ve been reminded of that over the past few weeks,

TODAY MARKS MY 200th article for HumbleDollar. Looking back, one recurring theme stands out: Managing our finances is, in a lot of ways, like managing our health.
Ask any doctor the recipe for good health and you’ll hear the same things: Exercise regularly, eat right, don’t smoke. It isn’t complicated—and yet it isn’t so simple. Environmental factors, genetics and bad luck conspire against us. Result: Even the most disciplined person isn’t guaranteed perfect health.

LONG-TERM-CARE insurance policies are, in my opinion, both a blessing and a curse. They’re a blessing because they can help cover critical and costly care when a family might have no other financial options.
But they can also feel like a curse. That’s because of what many owners of traditional long-term-care (LTC) insurance refer to as “the letter.” This is the renewal letter that policyholders receive each year. These letters provide a menu of renewal options,

THE FEDERAL RESERVE caught the market by surprise this past week. In fact, it seemed like Fed policymakers caught even themselves by surprise.

Previously, they had been forecasting that interest rates would stay near zero through 2023, on the assumption that inflation would remain manageable. But as the country has emerged from hibernation, inflation has run much hotter than expected. As a result, an increasing number of Fed officials now expect they’ll have to raise rates much sooner.

TYPE THE WORDS “safe withdrawal rate” into Google and it’ll return more than a million results. I’m not surprised by this. People debate practically everything in personal finance, but the debate around this question is particularly intense.

For at least 25 years, the conventional wisdom has been that it’s safe for retirees to base portfolio withdrawals on the 4% rule. But not everyone agrees. Some feel that percentage should be higher, while others feel it ought to be lower.

WHEN IT COMES TO financial questions, there are two common reasons people disagree. Sometimes, they disagree about the facts—whether, say, interest rates are headed higher. But sometimes, people disagree for another reason: They see the world through different lenses.

Last week, I mentioned that Ray Dalio, a prominent hedge fund manager, had recently said that bonds “have become stupid.” I disagreed, but not because of the facts. There’s no disputing the impact of today’s low rates.

A TEL AVIV WOMAN named Anat decided to surprise her elderly mother with a gift. Noticing that her mother had been sleeping on the same worn-out mattress for decades, Anat replaced it while her mother was away from the house. She then took the old mattress out to the curb.
It wasn’t until the next morning that her mother noticed the change and asked what had happened to the old mattress. Anat explained that she had put it out with the trash,

LET ME TELL YOU about Alvan Bobrow. His tale—and specifically his lawsuit—are important for every investor to understand. That’s because the legal loophole he sought to exploit is now a pothole for everyone else.

The first thing to know about Bobrow: He’s a tax attorney and, back in 2008, he had a clever idea. In need of cash, he took a $65,000 distribution—the technical term for a withdrawal—from his IRA. Ordinarily, a distribution from an IRA (unless it’s a Roth IRA or includes nondeductible contributions) is treated entirely as taxable income.

CONGRESS IS BACK at it, aiming to change the tax laws again. Just since 2017, there’s been the Tax Cuts and Jobs Act (TCJA), the SECURE Act and the CARES Act, each of which contained tax provisions, some very significant. As I type this, Congress and the White House are horse-trading on another round of changes.
Because new legislation is still being negotiated, I think it’s too soon to change your financial plan. But there’s one strategy that makes sense for a lot of people,

AN MIT PROFESSOR named Edward Lorenz published a paper in 1972 titled Predictability: Does the Flap of a Butterfly’s Wings in Brazil Set off a Tornado in Texas?

It was a catchy title. Though Lorenz didn’t mean it literally, the basic idea was that events in the physical world are highly interconnected—more so than they might appear.

The world of investments is similarly interconnected in ways that aren’t always visible. Just like the weather,

ON FEB. 27, 1992, Stella Liebeck ordered a cup of coffee from a McDonald’s drive-through. Moments later, as she attempted to open the lid, the cup spilled, causing a burn that sent her to the hospital. Her injury was serious but self-inflicted and not life-threatening. Nonetheless, she sued McDonald’s, and a jury awarded her almost $3 million. That award was reduced upon appeal, but this case is often cited as an example of an out-of-control legal system exploited by personal injury lawyers.

IN RECENT MONTHS, there’s been a lot of handwringing about the stock market. Thankfully, we seem to be on the back end of the pandemic, but things remain far from perfect in the economy. Millions are still unemployed. And the government has had to spend trillions to get us through, adding to a federal debt that was already enormous.

Today, the economy is far more fragile than it was pre-COVID. And yet the stock market just keeps cruising to new all-time highs.

IN THE INVESTMENT world, inflation is the topic of the day. There are four key reasons:

Congress. Since March 2020, the federal government has dropped more than a trillion dollars of cash into the economy via stimulus checks and the Paycheck Protection Program. While many of the recipients were unemployed and needed these dollars to meet basic needs, others were not. The result: More money in people’s pockets allowed them to spend more,

IS THE STOCK MARKET too high? It’s a question I’ve heard a lot recently. Each time, I’ve offered this recommendation: It’s impossible to predict where the market will go next, so your best defense is to have an appropriate asset allocation. But how exactly can you determine an ideal allocation?
The textbook method originated in the 1950s, with the work of a PhD student named Harry Markowitz. Up until that point, investors had mostly picked stocks and bonds in a vacuum,

SCOTT ADAMS, the creator of Dilbert, has this to say about making forecasts: “There are many methods for predicting the future. For example, you can read horoscopes, tea leaves, tarot cards, or crystal balls. Collectively, these methods are known as ‘nutty methods.’ Or you can put well-researched facts into sophisticated computer models, more commonly referred to as a complete waste of time.”
This is funny but, for the most part,

WHEN I WAS GROWING up, one family in the neighborhood lived differently from all the others. In their garage was a Rolls-Royce. When each of the sons turned 16, a new BMW showed up in the driveway. Because it was so out of the ordinary, it caught my attention. It caught everyone’s attention.
Looking back, this is what I find interesting: This kind of privileged upbringing looked like a guaranteed recipe for demotivating their children.

IN THE ONGOING battle between those who believe that the stock market is in a bubble and those who don’t, you may have heard mention of something called CAPE, short for cyclically adjusted price-earnings ratio. Among market indicators, it has the strongest track record in predicting future market returns.
What does the CAPE ratio say about today’s market? It’s flashing red. According to CAPE, the U.S. stock market is more overpriced today than it has been at any time since the 2000 market peak.

AT LEAST ONCE A DAY, I find myself saying, “Another truism of financial planning is….” To be honest, I don’t know whether the 12 concepts below meet the strict definition of “truism,” but I’ve found them hugely helpful in navigating the world of personal finance:
1. There are always two answers to every question. There’s the mathematical answer and there’s the “how do you feel about it” answer. It’s okay—and, in fact,

FOR MORE THAN a year, veteran investment manager Jeremy Grantham has been arguing that the U.S. stock market is in a bubble. And not just an ordinary bubble, but “an epic bubble… one of the great bubbles of financial history, right along with the South Sea bubble, 1929, and 2000.”
And yet, despite Grantham’s concerns, the market has only continued to march higher. In a recent interview, Grantham reiterated his concerns in even stronger terms.

ECONOMIST JOHN Maynard Keynes once observed that, “It is better for reputation to fail conventionally than to succeed unconventionally.” This is probably true in many realms. It’s certainly true in the investment world.
As the last 12 months have demonstrated, extreme and unexpected events can and do happen. But analysts whose job it is to make economic forecasts rarely go too far out on a limb. Sure, there are some forecasters who will take a chance with a view that’s far outside the consensus.

CHIMAMANDA ADICHIE coined the term “single story” in 2009. A novelist and a native of Nigeria, Adichie first came to the U.S. to attend college. Almost immediately, she was struck by the one-dimensional lens through which many saw her. It started with her roommate.
Knowing that Adichie had just arrived in this country, her roommate—an American—asked how she was able to speak English so well. Adichie had to explain that English is Nigeria’s official language.

BACK IN 2017, I WROTE about an oddity in my portfolio—an actively managed mutual fund that I bought without much thought to how it fit with my overall financial goals. Today, I have a confession. That fund isn’t the only oddity I own. In the interest of transparency—and because I hope readers will find it instructive—here are five more oddities, plus the thinking behind each:

While I firmly believe that low-cost index funds are the best way to build wealth and I believe that stock-picking is a fool’s errand,

IN THE FAMILY TREE of investors that began with Benjamin Graham sits a quiet, 100-year-old firm called Tweedy, Browne. This week, it published a chart that offered a new angle on a key debate in the world of personal finance: Is value investing dead—or just resting?
Before I get into the details of the Tweedy chart, I’ll back up and first recap the concept of value investing and why there’s a debate about it.

EVERY SO OFTEN, an arcane topic jumps from obscurity into the headlines. Such was the case last week when everyone was suddenly talking about the “short squeeze” on Wall Street. Below I’ll explain what happened and offer four thoughts on how to respond.
What does it mean to short a stock? In simple terms, it means you’re betting a stock will decline in price.
How does one accomplish this? First,

A FEW YEARS BACK, I found myself in the emergency room, thinking I had a serious condition. As I sat there, I worried about my family, including my wife and young children. If I didn’t come home, would my wife have a clear picture of our finances?
Fortunately, the health scare turned out to be a false alarm, but it was a wakeup call. Sure, I had an estate plan, but I realized that a binder full of legalese wasn’t enough.

THE CAPITOL WAS invaded by an angry mob 11 days ago. A week later, the House of Representatives voted to impeach the president. But if you’d been looking only at the stock market, you would have no idea.
Not only is the market higher today than it was the day before this all started, but also the VIX—the market’s “fear gauge”—is lower. From the perspective of the stock market, it’s been an ordinary few weeks.

IT’S GETTING TO THAT time when New Year’s resolutions start falling by the wayside. Most people don’t worry too much about this. But it would be nice if there were a way to give resolutions more of a shelf life.
Todd Herman, a performance coach who has trained dozens of Olympic athletes, offers one possible solution. He calls it the “90-day year.” The premise is that a year is just too long a timeframe.

WHEN I THINK BACK to Finance 101, what I recall—more than anything—is a whole lot of formulas. First came the calculation for present value, then formulas for valuing bonds, stocks, options, futures, forwards and all sorts of other financial instruments.
This was interesting. But with each passing year, I’ve come to realize that this introduction to finance was also incomplete. It was incomplete because—to state the obvious—the real world doesn’t always adhere to formulas.

WHEN I THINK BACK on 2020—and I know we aren’t quite done with it yet—I’m reminded of the movie Alexander and the Terrible, Horrible, No Good, Very Bad Day. But to paraphrase Nietzsche, chaos isn’t all bad—if something positive ultimately emerges from it.
Below are five financial lessons that, in my mind, are worth carrying beyond this year:
1. Stock prices respond to news—but never in a predictable way. Leading up to the election,

YOU’RE DRIVING DOWN the highway when, all of a sudden, a maniac goes speeding by, weaving in and out of lanes. Most of us have experienced this—and most of us have the same reaction. “That guy is crazy,” we think to ourselves. “If he doesn’t slow down, someone’s going to get hurt.”
But suppose that an observer instead responded, “That fellow’s speed is perfectly appropriate. Nothing at all wrong with it.” Now, you might think it’s the observer who’s the crazy one.

SO MUCH OF PERSONAL finance is focused on our future self—and that’s a challenge. Think about the standard prescriptions: Open an IRA. Maximize your 401(k). Save for college. Save for retirement. Build an estate plan.
These are all about the future—often the very distant future. An enormous amount of time and energy is spent planning for “someday.” But it’s equally important to focus on things that can be done to benefit you today.

IT’S THAT TIME OF year again, when Wall Street strategists begin publishing their market forecasts for next year. If you’re wondering whether to put any stock in those glossy publications, here’s my recommendation: Think back a year to the forecasts issued at the end of 2019. Did any of them predict that a virus would come out of left field, throwing the economy into recession, triggering a bear market and killing more than a million people worldwide?

WHEN I WAS A KID, I never liked the game Monopoly. I found it slow and uninteresting. But now, as a parent, I see its value. I’ve tried a lot of things to teach my children about money, but nothing comes close to Monopoly in its ability to convey important personal finance lessons.
Sure, it helps kids practice basics like addition and subtraction—but there’s a lot more to it. If you’ll be spending time with children over the holidays,

CONGRATULATIONS ARE in order for Jay and Kateri Schwandt, a Michigan couple who recently welcomed a new baby girl. This might not seem like an event that’s worthy of national news, except this is the Schwandt’s 15th child—and the first 14 are all boys. In an interview, Jay Schwandt said he didn’t think a girl was even possible: “You know after 14 boys, we just assumed perhaps medically it just wasn’t meant to be.”
The Schwandt’s new baby illustrates a point that’s often debated in the world of personal finance: When you see a pattern,

I’D LIKE TO TELL YOU about a unique new book. How I Invest My Money is a compilation of personal money stories shared by 25 investment professionals. The book takes its title and inspiration from a 2019 blog post by investment advisor Josh Brown, a widely followed author and TV commentator.
Brown’s motivation: After years of on-air commentary, discussing every conceivable financial topic, it occurred to him that no one ever asks investment people how they invest their own money.

I’D LIKE TO DESCRIBE—and recommend to you—what I’ll call the John Cleese approach to financial planning. It is, in my view, the simplest and most effective way to think about saving for retirement or any other goal.
John Cleese, the English actor and comedian, is largely retired. But in an interview, he described his approach to getting work done. When he had a weekly TV show, Cleese said, he didn’t worry about being unproductive some days.

AT 82 YEARS OLD, investment manager Jeremy Grantham has seen his fair share of market cycles. And as a U.K. native living in the U.S., he has the interesting perspective of an outsider. In a recent interview, Grantham shared his unvarnished view of the U.S. market. “American capitalism has become fat and happy,” he said. The U.S. stock market is in a bubble that will likely burst within “weeks or months.”
I don’t believe anything should be judged over the span of a single week.

TESLA JUST REPORTED financial results for its most recent quarter. For the fifth time in a row, it announced a profit. This was notable for a few reasons. Among them: Tesla’s increasingly strong performance again raises the question of why it’s been excluded from the S&P 500-stock index.
By way of background, the S&P 500 includes almost all of the 500 most valuable publicly traded companies in the U.S. But Tesla’s stock isn’t included,

STOCKS WENT INTO a freefall earlier this year, as I’m sure you recall. But all of a sudden, on March 23, everything changed. The market turned around and, just as quickly as it had dropped, it rebounded. Remarkably, the U.S. stock market is now in positive territory for the year.
What happened on March 23? The situation with the virus didn’t get any better. And it wasn’t Congress or the White House. What happened was that the Federal Reserve issued a statement.

I’VE DISCUSSED THE election in my recent articles and cautioned against timing the market. But if market timing isn’t recommended, what can you do to keep your finances on track through this potentially turbulent period?
Last week, I suggested reviewing your finances through the lenses of leverage, liquidity and cash flow. This week, I’d like to share another framework—and this is one you could employ at any time and not just in times of worry.

WITH THE ELECTION just a month away, many investors are worried about what lies ahead. Does it make sense to lighten up on stocks now, in advance of the election? I see at least four reasons not to sell:

Despite the polls, we can’t be sure what the result will be.
As we saw in 2016, nobody knows how the market will react to that result.
Even if the market reacts negatively, the effect may be temporary.

DO ELECTIONS AFFECT the stock market? Last week, I cited an analysis by Vanguard Group that attempted to answer this question. The study’s verdict: “It’s understandable to have concerns about the election. But as far as your portfolio and the markets are concerned, history suggests it will be a nonissue.” Specifically, Vanguard’s analysis cited evidence that investment returns are no different in election years than in non-election years.
I agree with Vanguard’s overall recommendation—to stay the course with your financial plan.

IN THE BOOK OF JOAN, a tribute to the comedian Joan Rivers, her daughter Melissa shares some of her late mother’s quirks. Among them: Her mother always drove 40 miles per hour. Regardless of where she was—on the highway, in a school zone, in the driveway—she always drove 40 miles per hour. Melissa’s conclusion: For passengers, this could be hair-raising, but at least her mother was consistent.
When it comes to investing,

DOES WEALTH BRING advantages? Yes—but it can also invite some unique challenges. Consider country music singer Kane Brown.
Shortly after moving into a new home, he went for a walk. He told his wife he’d be back in half an hour. But seven hours later, after getting lost, he ended up calling for help. What was unique about this episode is that, the entire time he was lost, Brown was on his own property.

TWO WEEKS AGO, I described how to scour your portfolio for holdings that no longer fit your financial plan. At a high level, these investments fail at least one of two tests:

Risk. Some investments are just inherently unsuitable or excessively risky. Alternatively, an investment might be perfectly fine, but it represents a big risk simply because you own so much of it.
Return. You might have an investment that has chronically underperformed,

INVESTING IS JUST one ingredient for financial success. In fact, one of the best routes to financial security is also one of the most obvious: Increase your income.
In the middle of a pandemic, this might seem like a tall order. After all, most people’s work and home life have been turned upside down this year. But it’s for precisely that reason that I wanted to pull together the following time-tested strategies for increasing work productivity.

THE STOCK MARKET hit a milestone last week, surpassing its pre-coronavirus all-time high. There’s a lot of debate about whether this is justified or sustainable. But the bottom line is, your portfolio today probably looks very different from the way it looked six months or a year ago. This may be a good time to take stock of what you own and to consider whether changes are warranted.
Back in February, I talked about the importance of asset allocation—and that’s a critical first step.

LAST SUNDAY, I discussed six strategies that could help you avoid decisions you’ll regret. But what if it’s too late—and you’ve already made a financial choice that’s left you unhappy? Now what?
Below are six notions to help you manage, and hopefully minimize, your regret over past decisions:
1. Your imagined happy ending likely wouldn’t have happened. Back in 2004, I recall seeing an iPod for the first time. A co-worker had received one for Christmas.

LAST WEEK, I LEARNED the disappointing news that our next-door neighbors—possibly the nicest people in the world—have put their house on the market.
While I’m sorry to see them go, I understand their decision. With a growing family, they’re looking for more room. During the pandemic, in fact, many people are making changes of one sort or another. Will they be happy with their choices?
That brings me to a new project, developed by author Daniel Pink,

THE TRICKY THING about investing is that there’s no single “right” approach. In an earlier article, I described the approach I favor—what I call the five minds of the investor, which involves being part optimist, pessimist, analyst, economist and psychologist.
But there are many other ways to be successful: You might invest in real estate, or follow a quantitative investment strategy, or invest in private companies. There are plenty of people who do very well with these approaches.

THEY SAY A PICTURE is worth a thousand words. But what about a chart?
A few weeks back, I noted that the stock market had become unusually top-heavy, with just five companies—Alphabet (i.e. Google), Amazon, Apple, Facebook and Microsoft—accounting for 20% of the overall value of the S&P 500. A chart that appeared online last week illustrates the impact of that imbalance. What it showed, in a nutshell, is that the overall S&P 500 is around breakeven for the year,

IN RECENT WEEKS, I’ve focused on some of the growing risks in the financial system. In the stock market, there are day trading enthusiasts and their obliging brokers. In Washington, there’s a Federal Reserve that has served up a seemingly bottomless punch bowl of new money.
Result: Despite the current recession and 11% unemployment, the stock market is close to its pre-coronavirus all-time high, fueled in part by the Fed’s policies, which have driven income-starved investors to take greater risk.

LAST WEEK, I TALKED about some of the unsettling trends in the financial markets. In that article, I focused on the role of brokers and day traders, and noted that it takes two to tango. But it turns out the dance floor is quite a bit more crowded than that.
Yes, brokers and day traders are doing their part, but there’s another set of actors who are less visible but a whole lot more influential.

IN HER MOST RECENT book, former Secretary of State Madeleine Albright quotes Mussolini. “If you pluck a chicken one feather at a time,” he said, “no one will notice.”
Don’t worry, I’m not veering into political commentary. But when I heard this quote, it brought to mind what we’ve been seeing in the financial markets this year. Taken individually, there’s nothing that strikes me as a clear red flag. But taken together, the current environment looks a little bit like a chicken that—all of a sudden—seems to have lost a whole lot of feathers.

THIS PAST WEEK, I received an email from a reader—let’s call him Tom. He described his experience during this year’s unruly stock market. After the market dropped in February and March, he said, the stock side of his portfolio lost a lot of its value. He decided to rebalance—that is, to buy more stocks so his original asset allocation would be restored. That is just what I would have done. But the key question—always,

I CAME ACROSS a statistic so surprising it was hard to believe: During the recent market downturn, according to Fidelity Investments, approximately 15% of investors sold all of their stock holdings. And among investors age 65 and older, nearly a third sold all their stock market investments. It was a discouraging figure, meaning that large numbers of people had picked exactly the wrong time to abandon their investments.
Fortunately, the figures were corrected a few days later.

AS AN INDIVIDUAL investor, what’s the key to success? It’s a question I hear a lot, especially in volatile times like this.
The answer, I think, is that there isn’t just one key, but rather five. The most successful investors seem to be equal parts optimist, pessimist, analyst, economist and psychologist. Together, I call these the five minds of the investor. If you can develop and balance all five, that—I believe—is the key to investment success.

EVERY YEAR, WHEN spring rolls around, investment folks trot out a favorite catchphrase: “Sell in May and go away.” This is based on the idea that the stock market lags during the summer, as people go on vacation.
While it may sound hokey as an investment rule, it’s hardly the only one. There’s also the January effect, which says that stocks do better just after the new year. Its cousin, the January barometer, stipulates that the market will have a good year if it has a good January.

IF YOU HAVE A SURPLUS in your household budget, what’s the best use for it? Does it make more sense to pay down debt or to invest those extra funds? With interest rates at such low levels, this is a question I’ve been hearing with increasing frequency.
Suppose your mortgage rate is 3.5%. If you pay down that debt, it’s like earning 3.5%. By contrast, if you invested in the stock market, your annual return would be uncertain.

EARLIER THIS YEAR, before the coronavirus hit, my family visited an amusement park. Everyone had fun—except my nine-year-old, who complained about the injustice of the rigged “down the clown” game.
You have probably seen this sort of thing: You’re given a handful of baseballs. Then, standing from about 10 feet away, the challenge is to knock down as many mechanical clowns as possible for a chance to win a prize. It doesn’t appear difficult—you aren’t that far away and the clowns are tightly spaced—but most people walk away empty-handed.

CONVERSATIONS ON Twitter aren’t known for their civility. Still, it came as a surprise last week when, out of the blue, author Nassim Nicholas Taleb launched a broadside against investor Clifford Asness, calling his work “crap,” along with other insults.
Asness wasted no time firing back, calling Taleb “very wrong and clearly both nuts and a world class terrible person.”
From there, the insults escalated: nasty, overrated, unoriginal, illogical, pretentious, emetic. That last one I had to look up in the dictionary.

WITH EVERYTHING that’s been going on recently, one story that’s received less attention is the ongoing spat between the White House and the board of the Thrift Savings Plan (TSP). As of a few days ago, there had been a ceasefire in the debate, but it isn’t over. It’s worth understanding what’s at stake—because the underlying issue has been a recurring theme in the investment industry.
If you aren’t familiar with the TSP, it’s one of the retirement plans available to federal government workers.

ON JAN. 10, 2000, America Online co-founder Steve Case stood on stage in New York to announce the largest corporate takeover in American history, buying venerable Time Warner for $165 billion. At the time, commentators called it the merger of the century. But just five years later, Case acknowledged that it was actually “the worst merger in history” and argued that it was time “to take it apart.”
Making financial decisions is difficult even in good times.

IT’S OFTEN SAID investors are driven by fear and greed. But I’d add a third item to the list: regret.
The past year and a half have been enough of a rollercoaster to rattle even the most even-keeled investor, creating ample opportunity for regret. Since the fall of 2018, the stock market has dropped 20%, gained 30%, dropped 35% and then gained 30% again. Result? Here are some of the sentiments I’ve been hearing over the past month:

“Why didn’t I sell at the top?”
“Why didn’t I buy at the bottom?”
“Why did I bother with international stocks?”
“Why did I buy high-yield bonds?”
“For the love of God,

I JUST CAME ACROSS a magazine article from the B.C. era—before coronavirus. The article, which appeared in a popular personal finance magazine, described a certain type of bond investment. The writeup was well researched and balanced, including a discussion of various risks.
In fact, the author raised the possibility of an economic downturn. How did he assess that prospect? “Recession, as always, is a risk,” he wrote, “but where’s the recession? Not seeing it,

I HAVE A BIG PROBLEM with a small word. But before I get to that, I’ll start with a little bit of history.
In his book The Success Equation, Michael Mauboussin tells this story: Back in the 1970s, a Spanish man won the country’s biggest national lottery, called El Gordo—the Big One. Awarded annually at Christmastime, it’s the rough equivalent of our Powerball. In this particular year, when the winner was interviewed,

WHEN I WAS IN GRADE school, I remember a field trip to a highflying local company called Prime Computer. At the time—it was the 1980s—Prime was a Fortune 500 company with a popular line of minicomputers and a runaway stock. Today, Prime is long gone and barely remembered. A Wikipedia page is about all that remains.
For a long time, I didn’t understand this. How could a company so successful simply cease to exist?

ON APRIL 14, 1988, Captain Paul Rinn was the commanding officer of the USS Samuel B. Roberts when it struck a mine in the Persian Gulf. The resulting explosion tore a 21-foot hole in the side of the frigate. Almost immediately, the ship began taking on water and multiple fires broke out.
Naval protocol for this situation was clear: Put out the fires first, then worry about patching the hull. But after just a few minutes of firefighting,

BERKSHIRE HATHAWAY Chairman Warren Buffett, in his most recent annual report, described an event that occurred at a Berkshire subsidiary last year. Late one night, a fire spilled over from a neighboring business, resulting in significant damage to the Berkshire facility, forcing it to shut down.
Fortunately, no one was injured and, as Buffett notes, the losses will be covered by insurance. Problem is, one of the company’s largest insurers was, as Buffett put it,

LATE LAST YEAR, I described how Bill Gates used to take time out from his job running Microsoft to seclude himself for “think weeks.” For better or worse, many of us today are finding ourselves stuck inside, with more time on our hands than usual. If you’re growing weary of the endless news cycle, below are some ideas to help you make the most of this time.
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FOLLOWING THE STOCK market’s steep decline, sensible investors are faced with three alternatives. The first two are fairly straightforward, but the third option is worth some discussion.
1. Do nothing. If all of your assets are in retirement accounts and you’re comfortable with your risk level, you might choose to tune out the news and do nothing at all. Similarly, if your portfolio doesn’t include any stock market investments, you might opt to watch the market upheaval from a distance,

“HOW BAD WILL IT get—and how long will it last?” In my last article, I mentioned that many people had asked me those two questions. This past week, amid the continuing stock market tumult, some folks have been raising a third question: “Should I even bother investing in the stock market? It just seems crazy.”
It’s a fair question. On Monday, the market was up 4%, before dropping 3% on Tuesday. On Wednesday, it was up 4% again,

AMID THE PAST WEEK’S stock market downturn, many people are asking two questions:
“How bad will it get?”
“How long will it last?”
I can’t answer these two questions, and nor can anybody else. But I have an answer to a third question: “What should I do?” Below are seven thoughts:
1. Ask financial advisors what they recommend at a time like this and most will offer the same advice: “Don’t panic.” While I agree,

“FOLLOWING THE market’s recent banner year, should we just sell everything and get out?” I got that question recently, and it’s entirely understandable. Since hitting bottom in 2009, U.S. share prices are up fivefold, including the S&P 500’s 31.5% total return in 2019. 
Individual investors aren’t alone in asking this question. A few weeks back, at an industry conference, James Montier delivered a presentation in which he compared the U.S. stock market to “Wile E.

IT’S NO SECRET THAT mutual fund costs are critically important. In fact, when it comes to the performance of funds in the same category, they’re the single most important differentiator. In the words of Morningstar, the investment research firm, “If there’s anything in the whole world of mutual funds that you can take to the bank, it’s that expense ratios help you make a better decision.”
But how do you go about totaling up a mutual fund’s costs?

TESLA FOUNDER ELON Musk is, to me, the ultimate investment Rorschach test. To his supporters, Musk is a genius without equal. As one Wall Street analyst put it, “If Thomas Edison and Henry Ford made a baby, that baby would be called Elon Musk.” But to his detractors, Musk is an erratic individual and the leader of a money-losing company whose bravado has landed him in hot water with the SEC. 
Last week, Tesla’s stock encapsulated those contrasting views. On Monday and Tuesday,

AT LEAST ONCE A WEEK, I run across the sort of portfolio I like to call a “broker’s special.” While each is different, they typically include some mix of the following:

A handful of mutual funds with names like “New Economy” or “New Discovery” or “New Perspectives.”
Some commodity funds.
10 or 20 individual stocks.
Funds with names heavy on buzzwords such as “infrastructure” and “renewable energy.”
And, in some cases, master limited partnerships,

IN BERKSHIRE Hathaway’s 2006 annual report, Warren Buffett devoted several paragraphs to scathing criticism of the hedge fund industry. Their fees, Buffett wrote, were so exorbitant and so stacked against investors that they amounted to a “grotesque arrangement.”
Indeed, Buffett has frequently recommended that individual investors opt for low-cost index funds. To reinforce this point, he issued a public challenge in 2007: He would bet anyone $1 million that, over a 10-year period, a simple S&P 500-index fund would beat the performance of a portfolio of hedge funds.

“THE INVESTOR’S CHIEF problem—even his worst enemy—is likely to be himself.” So wrote Benjamin Graham, the father of modern investment analysis.
With these words, written in 1949, Graham acknowledged the reality that investors are human. Though he had written an 800-page book on techniques to analyze stocks and bonds, Graham understood that investing is as much about human psychology as it is about numerical analysis.
In the decades since Graham’s passing, an entire field has emerged at the intersection of psychology and finance.

JUST BEFORE Thanksgiving, something odd happened on Wall Street. Three of the major brokerage firms issued remarkably similar reports declaring the death of the “60/40” approach to investing. What exactly does this mean—and should you be concerned?
By way of background, 60/40 refers to a traditional and very common strategy for building portfolios: 60% stocks and 40% bonds. Historically, most university endowments, as well as many individuals, have chosen this mix of investments because it offers a reasonable balance,

IT’S THAT TIME OF year again—when magazine editors put on their Nostradamus hats to offer up get-rich-quick schemes for the new year. “What China’s Best Investor is Buying Now,” reads the cover of Fortune, along with “40 Stocks for the New Decade.” The magazine even praises perennially unpopular Goldman Sachs. “Not your father’s vampire squid,” Fortune says.
These kinds of headlines seem comical, but it turns out they may be good for more than just entertainment.

AS IF ON CUE, Ebenezer Scrooge recently showed up in Washington, DC. The result wasn’t pretty.
A bill known as the SECURE Act, a favorite of the insurance industry, had been stuck in Congress all year. But suddenly, on Dec. 20, it got tacked onto another bill and signed into law. As far as I can tell, the primary beneficiaries of this new law, which heavily impacts retirement plans, will be the IRS and the insurance industry—but probably not you.

WHEN BUILDING portfolios, why don’t I include real estate investment trusts? REITs are large, diversified real estate companies. Some own office buildings, while others own apartments, hotels, shopping centers or other kinds of property. An example is Simon Property Group, which owns more than 200 shopping malls across the country.
A REIT is, on the surface, just like any other company, but with one unique feature: Dividends aren’t optional. REITs are required to pay out virtually all of their income,

ACCLAIMED AUTHOR Malcolm Gladwell talks about the importance of adding “candy” to his writing. By this, he’s referring to the asides, trivia and factoids that he uses to hold readers’ interest. Gladwell is quick to note, however, that writing can’t be all candy, with no main course, just as it can’t be all main course with no candy. To be effective, he includes both substance and entertainment.
When it comes to your investment portfolio,

TURN ON THE RADIO and, it seems, you can’t help but hear the holiday classic It’s the Most Wonderful Time of the Year. My question: From an investor’s perspective, is this indeed the most wonderful time of the year?
Apparently, it is. According to a 2017 paper titled Holidays Financial Anomalies, three of the best days for the stock market are the days after Thanksgiving, Christmas and New Year’s.

IF THE NAME HARRY Browne doesn’t ring any bells, I’m not entirely surprised. Though he was twice a presidential candidate, he never captured more than 1% of the vote. Still, to my knowledge, Browne is the only financial advisor ever to run for the White House. 
As a Libertarian, some of Browne’s economic proposals were extreme—including, for instance, abolishing income taxes. But one of his ideas has stood the test of time: In his 1981 book, 

IT’S LATE NOVEMBER. Is there anything you can still do to trim your 2019 tax bill? There might be. One overlooked aspect of mutual funds is how they can significantly—though quietly—impact shareholders’ tax returns.
By way of background, mutual funds—including exchange-traded funds (ETFs)—are required to pay out to shareholders, on a pro-rata basis, all of the income that they generate each year. This includes interest paid by bonds, dividends paid by stocks and capital gains created when a fund sells an investment at a profit.

THIS MONTH SAW THE publication of a remarkable biography: The Man Who Solved the Market chronicles the life and career of hedge fund manager James Simons. Over the past 31 years, Simons’s Medallion Fund has clocked average returns of 66% per year. Even after Medallion’s fees—which are the highest in the industry—investors took home average returns of 39% a year.
By way of comparison, the U.S.

WHEN STEWART MOTT died in 2008, his obituary in The New York Times described him as offbeat. That’s probably a fair description. Mott’s father, Charles Mott, had been one of the founding shareholders of General Motors. As a result, the younger Mott didn’t need to work and instead pursued other passions.
Among his many activities, Mott enjoyed political activism, but he wasn’t a strict partisan. To underscore this, he once brought both a live elephant and two donkeys to a fundraiser.

IN WINTER 2012, I experienced what every traveler dreads: a lost bag. Stranded without so much as a toothbrush, I had to replace everything—and fast. At first, this seemed like a pain. But in the end, I came to see it as a blessing. Why? Replacing everything—from head to toe, including the toothbrush—became an unexpected opportunity for a fresh start.
To be sure, all I’m talking about here are clothes and toiletries. Still, the experience made me realize that,

A UNIQUE EVENT occurred earlier this month: A group who call themselves the Bogleheads held an investment conference in the Philadelphia area, near the headquarters of Vanguard Group. Since its inception in 2000, this annual gathering has brought together fans of Vanguard’s founder Jack Bogle, who died earlier this year. 
Bogle was beloved by his fans for his authenticity and iconoclastic views. He was so self-assured, in fact, that—after he retired from Vanguard—he didn’t hesitate to share his opinions,

CLAY COCKRELL HAS an unusual job. He describes himself as a psychotherapist treating the “1% of the 1%” in New York City. From this vantage point, Cockrell has gained unique insights into the lives of the extremely wealthy. What conclusions does he draw about money and happiness? “If you have an enemy,” Cockrell says, “go buy them a lottery ticket because, on the off-chance that they win, their life is going to be really messed up.”
This observation fits well with the aphorism that “money doesn’t buy happiness.” There’s a growing body of research supporting this view.

I FEEL LIKE A BROKEN record when I talk about the benefits of index funds. Indeed, index fund advocates—myself included—sometimes get a little preachy, so I won’t bore you with the same facts I’ve cited before.
Instead, I want to focus on a more subtle reason to index, which has been highlighted by the stock market’s behavior over the past year. You’ve probably heard the expression “a rising tide lifts all boats.” When it comes to the stock market,

IN THE INVESTMENT world, there’s a lot of nonsense and a lot of hot air. But a few people are like the Shakespeare of personal finance: There’s wisdom in virtually every word. Warren Buffett is probably the dean of this group. But another leading light is Peter Lynch, who in the 1970s and ’80s stewarded Fidelity Investments’ Magellan Fund with enormous success.
Lynch is largely retired today, but his plainspoken advice is as valuable as ever.

IN RECENT WEEKS, the world met WeWork founder Adam Neumann. The meeting did not go well. WeWork had been preparing an initial public offering for its stock and things seemed on track. But the IPO was shelved and Neumann was out of a job. 
The proximate cause: A Wall Street Journal profile of Neumann detailed the entrepreneur’s odd habits and fanciful notions. Among Neumann’s stated goals: to become president of the world,

PRESIDENT TRUMP recently criticized the Federal Reserve—yet again. Calling Fed Chair Jerome Powell and his colleagues “boneheads,” the president expressed frustration that they haven’t done more to lower interest rates. Specifically, the president said we should, “get our interest rates down to ZERO, or less.” That last part—“or less”—was key. Not only should rates be lower, he argued, but they should be below zero, as they have been in Europe.
Last week, the Fed did indeed cut short-term interest rates—by 0.25 percentage point.

A DOZEN YEARS AGO, on my first day of business school, the professor stood at the board and illustrated a concept called “present value.” Truth be told, over my remaining time in school, I don’t think I learned anything more important than I learned in that first hour. It is, in my view, the single most useful tool in all of personal finance. Below, I’ll walk you through the concept and then illustrate some ways it can help you make better financial decisions.

INVESTMENT MANAGER Michael Burry made waves last week when he issued an apocalyptic forecast: Index funds, he said, are in a bubble similar to the housing bubble that ended very badly in 2008. Burry couldn’t say when the crash would come, but noted ominously that, “the longer it goes on, the worse the crash will be.”
Burry acknowledged that he’s “100% focused on stock picking,” so—at first glance—his criticism seems not unlike other active fund managers’ criticisms of index funds,

NIKOLA TESLA WAS a brilliant inventor, with nearly 300 patents to his name. He also had some unique habits. Among them: Every night, before he sat down for dinner, he would ask his waiter for a stack of 18 napkins. He would then use them to carefully wipe down his silverware. Even at the Waldorf Astoria hotel, where Tesla lived for decades and where the silverware was presumably clean, Tesla insisted on this time-consuming process before every meal.

ON DEC. 17, 2002, Harry Markopolos walked out of his Boston office wearing an oversized trench coat and a pair of white cotton gloves. His destination: the John F. Kennedy Presidential Library. 
A quiet figure, Markopolos worked as the chief investment officer at a small firm that specialized in trading stock options. He had heard about a New York-based competitor that was apparently doing similar work, but with much greater success. Following his boss’s recommendation,

IN DECEMBER 1954, 23-year-old John Neff hitchhiked from Ohio to New York in search of work. A Navy veteran, Neff had recently graduated college near the top of his class, with a degree in finance. His hope: to land a job as a stockbroker. But despite these qualifications, Neff was turned down. Why? According to a biographer, the brokerage firm felt “his voice didn’t carry enough authority.”
It didn’t take long for Neff to recover from this setback.

WHEN IT COMES to your financial life, should you care what other people think?
I’ve always found this a tricky question. On the one hand, it’s easy to fall into the trap of keeping up with the Joneses. If you care too much about what other people think, life can become very expensive—and that can be detrimental to your financial health.
On the other hand, it’s also natural to want to be accepted by one’s peers.

A LITTLE WHILE BACK, I found myself in an Uber. The driver began to share his political views. Before long, it became clear that his point of view was well outside the norm. He explained that the Federal Reserve is not a government entity, as most people believe. Rather, it is privately owned by the Rothschild family. In addition, he said, the Rothschilds also control the president—not just this president, but the presidency in general.

MY FATHER-IN-LAW—known to his family as Papa—passed away earlier this month. After 96 years, he had developed a number of money habits that were unconventional but quite effective, including these three:
1. Focused frugality. Papa was frugal, but not in the conventional sense. He didn’t practice extreme frugality and saw no virtue in intentional self-denial. Rather, he practiced what I would call focused frugality. If something was important—his children’s education, for example—he was happy to write that check.

FRAUD WEARS MANY faces. But depending on who you believe, potentially the most unusual is that of Jeanne Louise Calment. For years, the French-born Calment, who claimed to have been born in 1875, was celebrated as the world’s oldest person. By the time she died in 1997, she would have been 122— if she’d been telling the truth. New research, however, casts doubt on Calment’s claim. 
The real story, it turns out, may be that Calment actually died many decades earlier—in the 1930s.

A NEW FIRM CALLED Life + Liberty Indexes has created what it calls the Freedom 100 index of emerging markets stocks. Unlike other indexes, which typically weight stocks by their market value, the Freedom 100 weights countries by measures of freedom. These include freedom of religion, freedom of the press and freedom of assembly, among others. In short, the Freedom 100 looks like it could have been created by the authors of our Declaration of Independence.

A FEW WEEKS BACK, a reader—let’s call him Karl—challenged me with a question. Why, he asked, don’t I recommend momentum investment strategies?
If you aren’t familiar with the term, momentum strategies seek to buy stocks that have done well in the past, with the hope that they will continue rising, while also selling stocks that have done poorly, with the expectation that they will keep falling.
Karl asked why, in a recent article, I had dismissed momentum investing as the sort of thing that would turn your portfolio into an “unpredictable stew,” even though research has found that it can be profitable.

JUST BEFORE Thanksgiving in 2017, a heartwarming story hit the news. A young woman from Philadelphia named Katelyn McClure had run out of gas on the highway and found herself stranded. By chance, a homeless veteran named Johnny Bobbitt was nearby and, in an act of selflessness, he gave McClure his last $20 to buy gas.
After making it home safely, McClure wanted to express her gratitude, so she set up a GoFundMe page to help Bobbitt get back on his feet.

IT’S GRADUATION season. Entering the workforce? Here are five steps to help you jumpstart your financial life:
1. Manage your debt. If you’re like many graduates, you have student loans. Depending on how much you owe, you may be wondering how best to allocate your new paycheck. Should you direct every available dollar toward your loans or does it also make sense to begin saving? While everyone’s situation is unique, I have two suggestions.

YOU’VE NO DOUBT heard this before: Asset allocation is the single most important investment decision. If you have the right mix of stocks, bonds, cash and maybe real estate, you sharply increase your chances of success. 
But how do you pick the right mix? There are rules of thumb based on age, there’s a statistical approach called Modern Portfolio Theory, there are risk tolerance questionnaires and there are cash flow-based approaches. Each delivers a different answer—because each emphasizes different factors.

I’VE LATELY BEEN getting a lot of questions about a pair of lookalike investments: U.S. Treasury bonds, which are currently yielding around 1.8% to 2.6%, and online bank savings accounts, which offer similar yields. In other words, you could earn just as much interest in a simple savings account as you could if you tied up your money for a period of months, or even years, in a government bond.
The question I keep hearing: “Why in the world would anyone choose government bonds?

WHEN POLITICAL parties set aside partisan bickering and agree on an issue, it’s worth taking note. Such was the case last week when the House of Representatives voted 417–3 in favor of a bill known as the SECURE Act. This legislation would represent the most significant set of changes to retirement rules in more than a decade.
Why the sudden bipartisan cooperation? For better or worse, both parties recognize that a growing number of Americans face a retirement crisis.

I’LL NEVER FORGET MY first interaction with Wall Street. I was in my early 20s and just getting started in my career, when I was introduced to a stockbroker—let’s call him Eddie. He was a pleasant fellow with a good reputation and all the trappings of success, including a DeLorean in the driveway. He seemed like a safe choice.
My interactions with Eddie were straightforward. He would call from time to time with stock ideas.

ONE SPRING DAY in 1995, McArthur Wheeler walked into two banks near his Pittsburgh home and robbed them at gunpoint.
His plan had one critical flaw: The disguise he chose didn’t hide his face at all. Instead of the usual stocking cap or hat and sunglasses, Wheeler made an unconventional choice. He applied a coating of lemon juice to his face. His reasoning: Lemon juice could be used to make invisible ink, so Wheeler figured it would have the same effect on his face,

WHEN WE ROLLED OVER into May, I was reminded of a saying I used to hear when I worked in the world of stock-picking: “Sell in May and go away.” The idea—based on questionable data—was that stocks lagged during the summer months.
This notion always seemed suspect to me. But even if it were true, I was never quite sure what to do with it. Should an investor sell everything on May 1 and then buy back on Labor Day?

A FEW WEEKS AGO, life changed for 24-year-old Manuel Franco of West Allis, Wisconsin. The winner of a recent Powerball lottery, Franco took home $326 million—and that’s after taxes. With a sum that large, it shouldn’t be hard for Franco to make his winnings last a lifetime.
And yet, more often than not, such windfalls deliver heartache rather than happiness. Consider Lara and Roger Griffiths, an English couple who, in 2005, won the equivalent of $3.2 million from their local lottery.

ON DEC. 7, 2005, a curious thing happened in a Harvard classroom. Prof. Michael D. Smith stood in front of a group of computer science students to introduce a guest speaker: entrepreneur and former Harvard student Mark Zuckerberg. What was curious was that the room was nearly empty. The class met in a huge lecture hall, but there were barely a dozen people in the room.
How could that be? Why was there so little interest in Zuckerberg’s presentation?

I RECENTLY CAME across an academic paper with an attention-grabbing title: “It has been very easy to beat the S&P 500.” Not just easy, but very easy. 
That got my attention because, in recent years, beating the S&P 500 has been anything but easy. In fact, it’s been maddeningly difficult. In eight of the past 10 years, domestic markets have outperformed international markets—by a wide margin. A dollar invested 10 years ago in the S&P 500 would be worth $4.37 today.

AS THE OLD SAYING goes, there are lies, damned lies and statistics. And then there’s investment performance, which may deserve a category all its own.
This topic came to mind recently when I saw a press release heralding the accomplishments of a retired nonprofit executive. Among the claims: that he had doubled the organization’s endowment. This struck me as impressive—until I considered it more critically. What did it mean that he had doubled the endowment?

I RECENTLY HAD the opportunity to attend a panel discussion that included the prominent investment manager Seth Klarman.
Not familiar with Klarman? The simplistic version of his biography has him as a hedge fund billionaire. While that’s true, it doesn’t do him justice. Klarman is more like a cult hero, at least in the investment world. Some call him the “Oracle of Boston.”
Google his name, and you’ll see him described as “the next Warren Buffett.” Search YouTube,

HAVE YOU EVER struggled with a financial decision? If you’re like most people, I suspect that the math wasn’t the hard part. Instead, more often than not, what makes financial decisions a challenge is the subjective element.
Financial decisions involve lots of variables—your future income, interest rates, housing prices, tax rates and more. We can make reasonable forecasts, but ultimately these decisions require us to make judgment calls without complete information, and that can be unnerving.

IN JANUARY 1946, a man named Stanislaw Ulam found himself confined to a hospital bed, having suffered an encephalitis attack. A brilliant scientist and a veteran of the Manhattan Project, Ulam wasn’t the type to sit idly while he recuperated. Instead, after playing innumerable games of solitaire to pass the time, Ulam began to examine the statistical aspects of the game.
Among the questions he asked: How can you accurately estimate the probability of winning a game?

IN MY ROLE AS a financial planner, I hear a lot of stories. By far the most appalling and upsetting relate to life insurance. All too often, insurance salespeople leave clients with policies that are simultaneously overpriced, inadequate and inappropriate.
Are you evaluating a policy? Here’s a quick summary of the most important considerations:
What type of coverage should I have? Life insurance comes in two primary flavors: term and permanent. Term insurance,

FEDERAL RESERVE Chair Jerome Powell appeared before Congress late last month and spoke in serious terms about the country’s debt situation. It’s worth understanding what Powell said—and how that might impact your investments.
Powell’s message: “The U.S. federal government is on an unsustainable fiscal path.” Specifically, “debt as a percentage of GDP is growing, and now growing sharply, and that is unsustainable by definition.”
Powell’s remarks mirrored those of the Congressional Budget Office (CBO).

LAST MONTH, The Wall Street Journal ran an article with a puzzling headline: “How China Pressured MSCI to Add Its Market to Major Benchmark.” Like a lot of market news, this arcane-sounding story came and went without much notice. But it’s worth pausing to understand what it was all about—and why it matters to you.
First, let’s decode the terminology in the article’s headline: A “benchmark” is another word for an index.

SUPPOSE YOU WALKED into a restaurant and they handed you a menu without prices. Would you conclude that: (a) everything is free; or (b) something funny is going on?
I doubt anyone would choose the first option. It defies logic. Yet this is how the 401(k) industry routinely operates—and large numbers of people are falling for it. According to a 2018 survey by TD Ameritrade, 37% of 401(k) participants mistakenly believe that their 401(k) retirement plan is a free employee benefit—that it carries no fees.

IN SUMMER 2000, the Art Institute of Chicago fell under the spell of a young hedge fund manager named Conrad Seghers. The allure? Seghers claimed that his funds, called Integral, offered “the highest Sharpe ratios in the industry.” The Sharpe ratio is supposed to measure an investment’s risk relative to its returns and is popular in the world of hedge funds. Convinced by this pitch, the Art Institute committed more than $40 million of its endowment to Seghers’s funds.

IMAGINE YOU’RE TRYING to guess the winner of a basketball or ice hockey game. Which of these methods do you think would work best?

Flip a coin.
Make an educated guess.
Gather data and conduct an informed analysis.

In a classic study, researchers Paul Slovic and Bernard Corrigan attempted to answer this question. Instead of basketball or ice hockey, they looked at horse racing, but the results are equally applicable.
In their study, Slovic and Corrigan asked expert handicappers to make predictions using varying amounts of data about the horses in a race.

IN THE WORLD of personal finance, researchers have long understood that behavioral biases negatively impact investors. Examples include recency bias, hindsight bias, confirmation bias and many others. These are all well documented. Recently, a group of researchers uncovered yet another investor bias: This one is called “alphabeticity bias.”
Alphabeticity, as you might guess, refers to the bias that can occur when choices are presented in alphabetical order. This bias, the researchers note, is found in a number of domains: In elections,

IN THE HISTORY of the investment industry, May 1, 1975, is a date to be celebrated. On that day, the industry took not one, but two, remarkable steps forward.
The first change was an action by the SEC to deregulate stockbrokers. For the first time in more than 100 years, brokers were given the freedom to set their own commission rates on stock trades. The result was a boon for individual investors. Today, instead of paying hundreds of dollars to trade a stock,

JAMES CLEAR, in his bestselling book Atomic Habits, offers this thought-provoking notion: Suppose a plane takes off from Los Angeles on its way to New York. But after taking off, the pilot turns the nose of the plane by an almost imperceptible 89 inches. Where will the plane end up? The answer: nowhere near New York. As it flies across the country, that 89-inch difference will take it hundreds of miles off course.

IN 2005, COMEDIAN Stephen Colbert popularized the word “truthiness.” This term, if you aren’t familiar with it, refers to something which seems like it should be true, but isn’t actually supported by evidence. Are stock market pundits guilty of truthiness? To answer the question, let’s look at a recent event.
First, some background: In the life of an investment analyst, there’s a rare but dreaded phenomenon known as a “profit warning.” This occurs when a company can tell,

ROBERT SOROS, son of billionaire hedge fund manager George Soros, has a surprising explanation for his father’s success: “You know the reason he changes his position on the market or whatever is because his back starts killing him.”
You read that right: The younger Soros attributes his father’s success to a sort of sixth sense—as if he can feel the market in his bones. He goes on: “My father will sit down and give you theories to explain why he does this or that.” But,

I RECENTLY RECEIVED some odd communications from mutual fund giant Vanguard Group.
First, it sent a white paper, “Here today, gone tomorrow: The impact of economic surprises on asset returns.” As the title suggests, this paper examines the relationship between the economy and the stock market. In particular, the authors asked whether accurate economic forecasts could help an active trader profit in the stock market. Their conclusion: To beat a simple buy-and-hold strategy, an investor’s predictions would need to be accurate 75% of the time.

PABLO PICASSO WAS ONE of the most influential, prolific and financially successful artists of the 20th century. Yet, if you had visited his studio at the peak of his career, you might have guessed otherwise: It was a mess and his work schedule was, at best, leisurely.
On a normal day, Picasso would stay in bed all morning and only get to work around 2 p.m. When he did work, according to a biographer,

A LITTLE WHILE BACK, a friend—let’s call him Paul—recommended a book with an unusual title: How Not to Die. As you might guess, it’s about health, nutrition and longevity. Since Paul is a cardiologist and knows a thing or two about what can land people in hospital, I took his recommendation seriously and immediately ordered a copy.
When the book arrived, I learned that the prescription for not dying isn’t so simple.

WITH INCREASING frequency over the past month, I’ve been hearing the question, “Why does the stock market keep going down? I understand why the market dipped when the Fed raised interest rates, but why does it keep going down day after day?”
If you’ve been feeling unnerved by recent headlines, you aren’t alone. After gaining 10% in 2018 through late-September, the U.S. stock market reversed course and gave up that entire 10% over the course of just two months,

IT’S FIVE WEEKS UNTIL the end of the year—which is five weeks during which you can do some valuable financial housekeeping. Here are seven recommendations:
1. Give tax efficiently. In the past, charitable contributions were a direct and easy way to lower your tax bill. But with the recent tax law changes, which include a big hike in the standard deduction and limits on some itemized deductions, this strategy doesn’t work as well.

THE MUSICIAN PRINCE died in 2016 at age 57, leaving behind a legacy of musical genius. Unfortunately, he also left behind an ongoing legal and financial mess. The issue: For reasons no one understands, Prince neglected to prepare even the most basic estate plan, leaving potential heirs squabbling over his fortune.
Under the latest tax law, passed late last year, only those with more than $11.2 million in assets ($22.4 million for a married couple) are subject to federal estate taxes.

RECENT WEEKS HAVE been challenging for our country. We’ve seen horrific terrorist attacks. The midterm elections suggest the U.S. is deeply divided. While the economy has been doing well, the stock market has started to wobble. October, in fact, was the market’s worst month since 2011.
For all these reasons, folks have been asking me whether they should steer clear of the stock market for a while, until the dust settles. That sounds sensible—until you realize the difficult steps involved:
Step 1: Predict what’s going to happen and when.

IS APPLE the greatest company ever? On the surface, it certainly appears that way. The company sells more than 450,000 iPhones every day. Customers love them: According to surveys, iPhone customer satisfaction stands at 98%. Last year, Apple’s revenues topped $250 billion, and in its most recent quarter the company saw profits jump 41% from a year earlier. Not surprisingly, the company’s share price reflects this success. Having gained 33% over the past year,

WHAT’S YOUR FAVORITE tax rate? This isn’t meant to be a trick question. If you’re like most people, your favorite rate is probably zero.
While a 0% tax rate is great, it isn’t easy to achieve. There’s just a handful of ways to create tax-free income. If you have young children, 529 accounts are a great option. If you earn a high income, you might buy tax-exempt municipal bonds.
And, of course, there are Roth IRAs.

IN THE MID-1990s, Federal Express had a problem. Though the company’s safety record was exemplary, regulators had proposed new rules that would have posed an operational nightmare for the giant shipper.
The company flew Boeing 727 air freighters that each accommodated eight containers. Though they had never had a problem, the government’s concern was that if two heavier-than-average containers were loaded next to each other, it could cause the plane to become dangerously unbalanced.

THE STOCK MARKET this year reminds me of one of those Rorschach inkblot tests. The broad U.S. market has gained more than 4%, including dividends, but it’s difficult to know what to make of it. Bulls point to this year’s tax cuts and believe that the market’s gain makes complete sense. Bears, on the other hand, note that the market has quadrupled in less than 10 years and conclude that it’s at an unsustainably high level.

AS YOU NO DOUBT noticed, the stock market took investors on a wild ride last week. On Wednesday, the Dow industrials dropped more than 800 points. On Thursday, the Dow lost another 546 points. Friday was better, up 287 points, but there was still plenty of stomach-churning volatility.
At times like this, I’m reminded of Warren Buffett’s motto: “You want to be greedy when others are fearful, and you want to be fearful when others are greedy.” While that certainly sounds logical,

MY 10-YEAR-OLD SON and I had a chance encounter last month with the commissioner of the Boston Police Department. After saying hello, he bent down and offered my son this advice: “Stay in school,” he said, “and listen to your parents.”
Often, the recipe for childhood success is just that simple. Ditto when it comes to managing money. The basic principles are usually pretty straightforward. But there’s one topic that often leaves people with a headache.

MY GRANDFATHER WAS from Queens in New York City. He was a great guy and taught me a lot. He was also a native New Yorker, so he was street smart and tough.
One day, while we were walking together down 47th Street, near Times Square, I stopped to look at the jam-packed window of an electronics store. My grandfather waited patiently, but cautioned me, “Careful, they’ll take the eyes out of your head.”
It was a funny expression,

ALBERT EINSTEIN reportedly once said, “Everything should be made as simple as possible, but not simpler,” or words to that effect.
When it comes to investing, I have always believed that the simplest approach is the best approach. But in recent years, a new type of investment has, I believe, crossed over into the “too simple” category.
This new type of investment: target-date mutual funds. If you aren’t familiar with them, target-date funds are mutual funds that typically buy other funds.

THE NOTED PHYSICIST Lord Kelvin reportedly declared in 1900, “There is nothing new to be discovered in physics now.” In the annals of inaccurate proclamations, this one stands out. Just a few years later, Einstein published his Theory of Relativity and, in the following years, proceeded to upend many of the scientific world’s longest standing and most deeply held beliefs.
The world of personal finance witnessed a similarly inaccurate prediction 76 years later. When the newly formed Vanguard Group launched its first index fund,

THE STOCK MARKET recently hit yet another all-time high. But instead of unalloyed glee, many investors are struggling with mixed emotions. They’re thrilled at their gains. But at the same time, they’re hesitant to put more money into a market that has already gained so much.
Result: Folks have been asking, “Isn’t there anything else I can buy?” Often, this leads to questions about alternative investments. Below is an introduction to the topic,

KANYE WEST, IT TURNS out, is one heck of an investor. According to a recent analysis, a group of West’s stock picks has beaten the overall market by 40 percentage points this year. It’s an astonishing result. What, if anything, can we learn from his performance?
First, some background: As you may know, West is married to Kim Kardashian, who is one of the dominant personalities on social media, so it was via Instagram that the world gained a window into these investments.

MY SONS’ BASKETBALL coach, George, has a favorite expression: He talks about “working through the uglies.” When you’re developing a new skill, he says, you shouldn’t expect to be perfect the first time or even the second. But if you keep working at it, over time there will be progress, “from ugly to not-so-bad to decent to good and then, eventually, to great.” The message is clear: You can’t rush it, you can’t skip steps and you have to start with the basics.

A CURIOUS THING happened in Stockholm in 2013. The Royal Swedish Academy of Sciences awarded the Nobel Prize in economics to three academics who had developed theories about stock prices. What was odd was that two of the recipients—Eugene Fama and Robert Shiller—couldn’t have been more opposed in their viewpoints.
Fama believes that stock prices are always rational and that there’s no such thing as a market bubble. Shiller believes that stock prices are often irrational and that bubbles do occur.

IF YOU’RE A FAN of basketball, you may be familiar with the Lopez twins—Brook and Robin. On the surface, they are identical in every way. Both stand seven feet tall. Both went to Stanford University. Both entered the NBA draft in 2008 and both were picked in the first round. Since then, both have enjoyed successful careers.
A casual observer would be hard-pressed to see any difference between the Lopez twins, but there is one: While they are both impressive players,

THE SELF-PROCLAIMED fortune-teller Nostradamus published more than 6,000 predictions during his lifetime. With the benefit of hindsight, it’s easy to see that his prophecies had little substance or predictive value. In fact, in his day, even astrologers dismissed Nostradamus as incompetent.
But what if the person making a prediction is the opposite of Nostradamus? What if he is a serious individual, someone who is universally respected and whose forecasts have a demonstrated track record of success?

IN THE FIELD OF epidemiology, researchers have long used the term “tipping point” to describe how epidemics occur. At first, an ordinary disease moves slowly, not gaining much attention. But then, seemingly overnight, it snowballs into something far larger.
Within the world of public health, this concept is well understood. But about 20 years ago, the author Malcolm Gladwell took a closer look and pointed out that tipping points can be found in a whole host of other situations far beyond epidemiology.

A QUESTION FOR YOU—a trick one, I admit: Should you invest in technology stocks, such as Apple?
My answer: Yes, certainly.
Another question, also a trick one: Should you invest in the stocks of entertainment companies like Netflix?
My answer: Again, yes, of course.
A third question: Should you invest in energy companies, such as ExxonMobil?
My answer: Again, yes.
You might wonder why I’m asking these questions and why I’m answering “yes” to all of them.

NOT LONG AGO, I RAN into my friend Martin, who works as a cardiologist at a local hospital. In the course of our conversation, I commented on the construction equipment outside his facility and asked what they were building.
His answer: “Building? No, they’re actually un-building.”
He explained that recently his hospital had been sold and the new owner was a for-profit company. As part of the transition, the new owner had evaluated the hospital’s facilities and discovered that a group of older buildings was largely unused.

WHEN YOU WERE growing up, did you ever hear stories like these?

“If you swallow gum, it will stay in your stomach for seven years.”
“If you keep making that face, it will freeze that way.”
“If you drink coffee, it will stunt your growth.”
“If you watch too much TV, your eyes will turn square.”

In hindsight, these stories are funny and harmless. But problems can arise if, as adults, we make important decisions based on misinformation.

IN THE SUMMER of 1789, George Washington got into a dispute with his Postmaster General—a fellow named Ebenezer Hazard—and removed him from office.
Looking for a new profession, Hazard decided to start an insurance company. He called his new firm the Insurance Company of North America and specialized in providing life insurance to ship captains. The business was a perfect fit for the times and quickly prospered. Still, I’m sure that even Hazard would be surprised to see his company still in business more than two centuries later.

“THERE ARE TWO kinds of people in the world…” There are Republicans and Democrats. Right-brained and left-brained. Yankees fans and Red Sox fans. And, of course, Starbucks people and Dunkin’ Donuts people.
In Boston, where Dunkin’ was founded and where I live, this is a particularly strong theme. Dunkin’ people and Starbucks people see themselves as very different. Starbucks aficionados see it as a higher-quality experience and don’t mind paying for it. Meanwhile, Dunkin’ fans are proud of their frugality and think that the people over at Starbucks are overpaying.

IN HER BESTSELLING book Thinking in Bets, retired poker champion Annie Duke stresses an important point: As kids in school, it was regarded as a failure if we ever answered a question, “I don’t know.” But in the world outside the classroom, the only honest answer to many questions is, “I don’t know” or “I’m not sure.” This isn’t due to ignorance. Rather, it’s because, in many cases, the precise right answer simply isn’t knowable.

MUCH PERSONAL finance literature, including most of what I write, focuses on how to handle money—how much to save, which investments to buy, and so forth. But what if you have a more fundamental question: How do I earn more in the first place?
To help answer that question, I have five new summer reading recommendations. Each of these books offers strategies to help you increase your productivity—and your happiness—on the job. That, in turn,

IN SUMMER 2011, a rural Illinois man named Wayne Sabaj was in his backyard picking broccoli, when something caught his eye. Half buried in the dirt, he found a sealed nylon bag. Inside was $150,000 in cash. For Sabaj, who was unemployed and had, in his words, “spent my last $10 on cigarettes,” this was a godsend.
Though it remains a mystery who had buried this particular stash of money, these sorts of finds are not uncommon.

IN MY WORK AS a financial planner, there’s one topic that always seems to raise an eyebrow: Social Security. When people see projections of future retirement benefits, they often respond with skepticism. My sense is that media reports, questioning the system’s solvency, have led people to discount the value of Social Security benefits—or disregard them entirely.
In my view, this is a mistake. While no one can guarantee what Social Security will look like in the future,

MY FRIEND ROSTISLAV, who would know, tells me that in Russian there’s no equivalent for the word “privacy.” That’s because privacy—as we understand it—is a foreign concept. Children’s grades are posted publicly in schools and it isn’t considered impolite to ask someone’s salary.
Why is this relevant? As a stock market investor, if you have international exposure, you’ll want to be aware of these cultural differences, because they impact how other countries run their economies and how they regulate—or don’t regulate—their investment markets.

PERHAPS YOU’VE HEARD the story of Ronald Read. A lifelong resident of Brattleboro, Vermont, Read was a quiet man. He preferred flannel shirts and spent much of his career as an attendant at a local gas station. Yet, when he died in 2014, even his closest friends were surprised to learn that Read had accumulated a fortune of more than $8 million.
Stories like this appear with some regularity. In 2010, Grace Groner, who was an administrative assistant in Lake Forest,

THE FEDERAL government recently issued its monthly inflation report. The resulting headlines could have put you to sleep: “Consumer Price Index Rises 0.2% in April.” It would have been easy to skip over this seemingly insignificant story for two reasons: First, the way the government reports inflation data, focusing on the monthly increase, isn’t terribly meaningful. Second, even if you looked at the annual rate, which is 2.5%, inflation just doesn’t seem like much of a concern.

EVERYBODY WANTS easy answers. But often, things aren’t so simple, especially when it comes to financial conundrums. Consider the four common money questions below—and the rules of thumb that folks frequently rely on.
1. How much do I need saved for retirement? Type this question into Google and most of the answers will recommend that you save some multiple of your income. Some suggest eight-to-10 times income, while others recommend as much as 25 times.

WHEN ASKED WHY HE robbed banks, Willie Sutton replied, “because that’s where the money is.”
Similarly, private investment funds—such as hedge funds and private equity funds—are attractive to high net worth investors, because they carry the potential for outsized returns. That, supposedly, is where the big money is. Several factors explain this potential. Among them: These funds not only use leverage to increase the size of their investment bets, but also they may buy investments that aren’t publicly traded—and hence they could receive higher returns because these investments are mispriced or as an inducement to accept their illiquidity.

SHOULD YOU INVEST in the stock market? The answer seems obvious: Over the past 90 years, stocks have returned an average 10% a year, far outpacing bonds at 5% and cash investments at less than 3%.
So why ask the question? The reason is the word “average.” Stock market returns are, of course, uneven from year to year and uneven from stock to stock. That’s well known. But the degree to which stock performance varies from stock to stock may surprise you—and that has implications for how you invest.

I REMEMBER SPEAKING with an industry colleague about a company that had been in the news. He told me that he liked the company’s stock and, in fact, had bought it for the mutual fund he managed. Then he added, parenthetically, “I owned it, then I sold it, then I bought it back.”
This discussion highlights a fundamental challenge for investors: Mutual fund managers face incentives that often diverge from their clients. Specifically, fund managers are graded and compensated for their performance before taxes.

ERIC SCHMIDT SAID this when he was Google’s chief executive: “If you have something that you don’t want anyone to know, maybe you shouldn’t be doing it in the first place.”
In his Congressional testimony last week, Facebook chief executive Mark Zuckerberg didn’t say anything nearly as condescending or abrasive. But his testimony was a good reminder that we’re in a very different world privacy-wise than we were even 10 years ago,

ANYONE WHO FOLLOWS my work knows I am a staunch advocate of index funds and believe that stock-picking is a difficult road. That said, there are three undeniable facts about picking stocks:

All of the great fortunes—Rockefeller, Carnegie, Gates, Buffett—were built by owning one stock: a very good one but, nonetheless, just one.
There are rare investors who are able to outperform the market averages by picking the right stocks. It’s hard, but it can be done.

IS FINANCIAL PLANNING a product or a process? In other words, is a financial plan a document that you can print, bind and put on your shelf—or is it an ongoing activity? This is something of a religious debate within the finance community.
Supporters of the “it’s a product” view are usually dyed-in-the-wool financial planners. Not surprisingly, they believe that financial planning should result in a physical plan—an exhaustive, detailed document that’s full of analysis and projections.

PERHAPS YOU’VE HEARD the expression, “There’s no free lunch.” The idea is, you usually don’t receive something for nothing. Whether it’s with money or with time and labor, you almost always “pay” one way or another.
It’s an interesting concept—but whoever coined the phrase clearly never looked at the U.S. tax code, which is full of free lunches. Today, we’ll discuss one example, which may be of interest to the charitably inclined.
One of the most talked about changes in the new tax law is a provision that alters how deductions are treated.

UNIVERSITY OF California finance professors Brad Barber and Terrance Odean published a research paper on investor behavior in early 2000. The results weren’t pretty. By their reckoning, individual investors lagged the overall market by an average of almost four percentage points a year. The culprit: the costs involved in trading individual stocks.
It isn’t just individuals who struggle with stock-picking. Professional money managers, on average, also trail behind the overall market. Over the past five years,

ON THE AFTERNOON of Sunday, Sept. 28, 1941, it was cool and damp in Philadelphia. Inside Shibe Park, where the hometown Athletics were suiting up to face the Red Sox, all eyes were on Boston’s 23-year-old slugger, Ted Williams. It was the last day of the regular season, and Williams’s average stood just a hair short of .400, at .39955.
According to baseball’s official rules, this would have rounded up to an even .400 in the record books,

SOMETIMES WE DON’T give kids enough credit. Last week, my first-grader reminded me of this fact. On a trip to CVS, he was looking through the drink cooler, when he asked, “What’s Smartwater?” Before I could answer, he started with his own commentary. Seeing the price tag—which was more than double that of the regular water next to it—he wondered, “Why’s it smart? It’s just water. Is it really going to make me smart?”
This made me realize something: As consumers,

THERE’S A NEW TYPE of financial fraud on the rise: tax refund theft. All an identify thief needs are an individual’s name and Social Security number. This information, unfortunately, is readily available. In a single incident in 2017, thieves stole information on almost half of all Americans from credit reporting agency Equifax.
Using this information, thieves then prepare and file a fake tax return in such a way that it appears a large refund is due.

“IN THIS WORLD,” Ben Franklin famously once wrote, “nothing can be said to be certain, except death and taxes.” But I would also argue that neither is completely out of our hands.
When it comes to our health, we all know that we should exercise, eat right and go for regular checkups. And when it comes to our tax bill, there’s quite a bit we can do to minimize it, especially in retirement. Below,

IN AUGUST 2004, venture capitalist Peter Thiel sat down to listen to a pitch from a 20-year-old entrepreneur named Mark Zuckerberg. It didn’t take long for Thiel to make up his mind. According to most accounts, they met in the morning and, after a short break for lunch, Thiel committed to buying 10% of Zuckerberg’s new company, Facebook.
In hindsight, this was clearly a smart move, making Thiel a billionaire. But while it was certainly a great investment,

I LOVE THE QUESTIONS that kids ask. This week, my first grader told me he had heard the word “caricature” and wanted to know what it meant. I explained it and then we went online to see some examples. In our highly politicized culture, we didn’t have to look far to see some exaggerated cartoon depictions of various political leaders.
It occurred to me, though, that our posture toward investments isn’t all that different.

WARREN BUFFETT ONCE quipped that, “You only find out who is swimming naked when the tide goes out.”
I’ve been thinking about this idea over the past two weeks, as markets around the world have given up all their year-to-date gains and then some. Since peaking on Jan. 26, the U.S. market, as measured by the S&P 500, has lost 8.8% of its value.
When the tide goes out like this, the emotional impact can be powerful—and the headlines just make it worse.

TED BENNA, INVENTOR of the 401(k) retirement plan, famously once stated that the system he created should be “blown up.” Why? It isn’t the fundamental structure, which he still believes in. What he doesn’t like is the complexity and costs that characterize today’s typical 401(k).
The original 401(k)s, he likes to point out, had just two fund options. Today, it’s more like 20. Because of that, it’s all too easy for bad investments and high fees to sneak in.

A YOUNG GRADUATE student named Harry Markowitz wrote a paper in 1952 that sought to prove, mathematically, the old maxim “don’t put all your eggs in one basket.” Through his work, Markowitz taught investors how to diversify their investments effectively, something that was not well understood at the time.
For instance, he explained that the number of stocks you hold is far less important than the number of types of stocks you own.

A FEW YEARS BACK, a fellow named Wylie Tollette faced uncomfortable questions as he sat before the public oversight committee of the California Public Employees Retirement System (CalPERS). Tollette, the pension fund’s Chief Operating Investment Officer, was responsible for updating the committee on the status of its massive $350 billion portfolio.
But when a committee member asked about the fees CalPERS was paying to a particular group of investment managers, Tollette did not have a ready answer.

THE STOCK MARKET had a great 2017, gaining more than 20%. But was that kind of gain justified—or should it worry us, especially after the market had already tripled in recent years? I think it’s useful to understand the range of viewpoints, so we’re better prepared for 2018 and beyond. Here are the bull and bear cases:
Bull Case. As measured by the S&P 500 index, the U.S. market gained nearly 22% last year.

AT SEVEN O’CLOCK THIS morning, as my wife and I tried in vain to wake our children for school, we heard a similar response as we went from room to room: “My head hurts.” Nobody wanted to get up.
I have to say, I don’t blame them. It’s the middle of winter here in Boston. The sky is gray and the thermometer seems stuck below zero. It can be hard for anyone to feel motivated,

IN A CLASSIC EPISODE of the sitcom 30 Rock, Tina Fey’s character, Liz Lemon, muses about the size of her nest egg: “I have money saved. Two years. Maybe four, if I cancel cable.”
Not worried about the size of your cable bill? In all likelihood, you’re fretting about one aspect of your financial life—and probably more than one. You might be wrestling with housing costs, student loans, the cost of putting your own children through school,

I AM AMAZED OUR schools don’t require kids to learn three important life skills: the basics of nutrition, a thing or two about parenting, and how to handle money. I’m no expert on nutrition and my parenting is a work in progress. But I do have a background in personal finance: When folks ask me what to read to deepen their financial knowledge, I have a ready list of titles.
Recently, however, someone asked me for a more advanced list—a “201”

I RECENTLY LEARNED a new expression, TL;DR, which stands for “too long; didn’t read.” Twitter users and bloggers use it when they want to summarize an idea for readers who are short on time. It’s the modern equivalent of saying, “Here’s the executive summary.”
Coincidentally, this week, two people separately asked me what I see as the most important principles in personal finance. In other words, they wanted the TL;DR version, without too much commentary.

I’M A BIG BELIEVER in transparency, so I’d like to tell you a little about my personal investments. As you might guess, the overwhelming majority of my money is allocated to simple, low-cost index funds—the same things I recommend in my writing and for my clients. That is true almost without exception. But today, I would like to describe one of those exceptions.
Many years ago, before I entered the investment industry, I purchased shares in a small mutual fund called the Mairs &

ONE OF MY FAVORITE activities as a child was to play with a tomahawk at my grandparents’ house. Yes, that was in the days before the Consumer Product Safety Commission. But in this case, it wouldn’t have made a difference: This particular tomahawk was no toy, but rather the real thing. It belonged to my grandfather. His name was Walking Buffalo, and he was a member of the Assiniboine, a Native American tribe who live on the Plains of Montana.

WHEN I LOOK AT TODAY’S world, I often think of Charles Dickens’s famous line, “It was the best of times, it was the worst of times.” Technology, including the web and smartphones, has made life so much more convenient.
Still, one thing I really miss from the “old days” is the experience of the traditional bookstore. Shopping online is great, but sometimes it’s easier to choose from a curated set of 10 books on a shelf than to sift through an unwieldy list of a thousand choices online.

WHEN AN INVENTOR goes on record stating that his invention is “a monster” that he’d like to “blow up,” you know there’s a problem.
Such is the case with Ted Benna, who back in 1980 created the first 401(k) retirement plan. Since then, his invention has grown to become the dominant retirement vehicle for millions of Americans.
Why is Benna so negative on his creation? The problem, in a word: complexity. According to Benna,

IN TODAY’S POLITICAL environment, discourse has become ever more fractious. The investment world, in my view, isn’t much better. Those who disagree generally talk past—rather than listen to—one another.
That is why, in my work as an investment advisor, I maintain a “team of rivals” approach, reading and listening to diverse opinions. Behavioral scientists often talk about confirmation bias—the tendency to seek out only information that confirms our preconceived notions. To counteract this bias,

IN MY HOMETOWN of Boston, there’s an old joke about our dismal winter weather. “February,” they say, “is the longest month of the year.” I don’t disagree and so, each year at Presidents’ Day, my family tries to get away for a warm weather vacation.
On these trips, we often stay at the same hotel and, because of that, we have noticed certain patterns. Among them: Most years, there is the same large corporate gathering.

LIKE MOST PEOPLE, I’ve made my fair share of financial blunders. I’ve also had some successes. But I definitely spend more time beating myself up over my errors than celebrating my successes.
Undoubtedly, my biggest mistake fits into the relatively obscure category of asset location. If you aren’t familiar with the term, I can explain it by way of an example. Suppose you have two investment accounts: a retirement account and a standard, taxable account.

WE’RE USED TO SEEING money as one of life’s limiting factors. But if you receive a financial windfall, money may no longer be the limitation it once was. While that might sound liberating, it can also create anxiety. The reality is, constraints serve a useful purpose: They provide structure. Without that structure, you may find yourself feeling rudderless.
I experienced this when I received a windfall several years back. I remember walking into an Apple Store,

ONE DAY BACK IN 2012, I received a life-changing windfall. Contrary to what you might imagine, however, that day was not very different from the day before it, or the day after. It went something like this: Woke up. Went to work. Came home. Thought about ways to splurge. Ultimately gave up and went to bed.
In other words, there was no visit to the Ferrari dealership, no trip to Las Vegas,