RECENTLY, A READER—let’s call him Tom—posed this question: If stocks historically have delivered far better returns than bonds, then why should an investor own any bonds at all? Even with the stock market’s unpredictable ups and downs, wouldn’t you end up way ahead by betting only on stocks over the long term?
It’s a fair question. Over the past 100 years, stocks have delivered returns of roughly 10% per year, while bonds have returned just 5%.
WHAT’S THE MOST important idea in personal finance? It’s hard to single out just one, but over the years, I’ve found the following dozen ideas to be among the most useful.
Whether it’s on TV or online, there’s never any shortage of market prognosticators. Especially during a bull market, everyone seems to have an opinion on where things are headed. The reality, though, is that people can only guess about how the economy, the market or any individual investment will perform.
IT’S BEEN AN UNUSUAL week in the bond market, and not necessarily in a good way. This has many investors questioning the value of bonds, which is understandable. Bonds are supposed to be the “safe” side of a portfolio, but they’ve struggled in recent years.
Arguably, the drama we’re seeing in the bond market today began more than 50 years ago. To put today’s situation in perspective, I’ll briefly summarize that long history. Then we can look at what steps you might take to better protect your portfolio from here.
FOR MUCH OF THE seventeenth and eighteenth centuries, European monarchs used a financial instrument known as a tontine to help finance their governments.
Tontines were first developed in the 1650s by an Italian government worker named Lorenzo Tonti and were similar to annuities: In exchange for a single, lump-sum purchase, tontines offered guaranteed payments for life. But tontines also offered some unique features.
Unlike an annuity, where payments end with the death of the owner,
RECENTLY, A FELLOW—let’s call him Tom—contacted me with a distressing story of financial fraud. I’ll describe what happened then review steps you might take to prevent this same sort of thing.
Tom first noticed there might be a problem when he spotted a larger-than-average withdrawal from his checking account. The payee was a 529 college savings plan. But because Tom and his wife—let’s call her Jane—have 529 accounts for their children, the transaction almost went unnoticed.
THE OPEN KITCHEN restaurant has been a fixture in Charlotte, North Carolina for 75 years. The restaurant has an old-time feel, with memorabilia, including menus from years gone by, lining its walls. Those old menus provided David Enna, a financial journalist, with a laboratory for examining the effects of inflation.
What did Enna find? The oldest menu on display is from 1963. To state the obvious, today’s prices make those from the 1960s look quaint.
SOME MILESTONES are auspicious. Others are not.
This week, the Treasury announced that the federal government’s debt had topped $40 trillion for the first time.
Government debt is nothing new, but the problem is now of more concern, for two reasons. First, the scale has grown. An apples-to-apples way to look at the government’s debt load is to compare it to GDP—the economy’s total annual output. On this basis, outstanding debt now exceeds 100% of GDP,
BY NOW, YOU’VE probably heard the story of the 25-year-old wunderkind Leopold Aschenbrenner. After graduating as valedictorian from Columbia University at age 19, he worked for FTX, the crypto trading firm, then found his way to OpenAI, where he worked as a researcher for about a year, until mid-2024.
In the months after he left OpenAI, Aschenbrenner wrote a 165-page paper titled “Situational Awareness,” in which he detailed his views on the future of artificial intelligence.
AFTER YEARS OF heady gains in the stock market, many investors are facing the same question: To manage risk, they’d like to cut back on one or more of their holdings. But because of the potentially costly tax bill that might result, they aren’t sure exactly how to do that.
How can you square this circle?
One easy option would be to donate appreciated assets to charity. But that would make sense only if it aligns with your charitable goals and,
AT FIRST GLANCE, Social Security appears straightforward. During our working years, we pay into it, and in retirement, it sends us a monthly check, guaranteed for life. Unfortunately, it isn’t always so simple. Below are five aspects of the system that are frequently misunderstood.
Benefits estimates. Look at a Social Security statement, and an easy-to-read chart provides estimates of the benefits available at various ages. The heading above the chart reads, “Personalized Monthly Retirement Benefit Estimates Depending on the Age You Start.” That seems clear.
WHEN IT COMES to financial decisions, many investors subscribe to an approach known as evidence-based investing. The idea, as the name suggests, is to base decisions, whenever possible, on data rather than on intuition or other informal methods.
This sounds logical. It isn’t perfect, though. Economic and financial indicators have weaknesses which are important to be aware of.
Consider, for example, the Cyclically-Adjusted Price-to-Earnings, or CAPE, ratio, developed by Robert Shiller, a Yale professor and Nobel laureate,
A TOPIC THAT’S been in the news recently is the so-called K-shaped economy.
Imagine a chart plotting the relative standing over time of those with higher incomes and those with lower incomes. Owing to a strong stock market and rising home values, the shape of the chart for those with higher incomes would extend up and to the right and has been moving increasingly in that direction since Covid.
Folks with lower incomes, on the other hand,
INNOVATION IN THE world of retirement plans is decidedly slow moving. But as of July 4th, investors now have a new savings option known as a Trump account. In short, these are retirement accounts designed specifically for children.
Trump accounts share some similarities with traditional individual retirement accounts (IRAs), but there are also key differences. If you have children, grandchildren, nieces or nephews, this new option may be worth exploring.
Who is eligible for a Trump account?
AS WE CELEBRATE 250 years since the Declaration of Independence, I’m reminded of an expression that’s popular in the investment world: “This time is different.”
The phrase dates to a 1993 publication titled “16 Rules for Investment Success,” authored by the veteran investment manager Sir John Templeton. Rule number 11 included the following admonition: “The investor who says, ‘This time is different,’ when in fact it’s virtually a repeat of an earlier situation, has uttered among the four most costly words in the annals of investing.”
Templeton’s message,
THE INVESTMENT WORLD is full of storytellers. And while these folks might be entertaining, they generally aren’t very helpful. There’s one category of stories, however, that I do think is useful: They’re what I might call investment fables. They’re apocryphal stories that likely aren’t real. But they’re helpful nonetheless because each carries a useful lesson. Here are some of the more popular ones.
Consumer choice. In 1999, Richard Mille and a partner launched a company to make wristwatches.
THE WAY INVESTORS think about the stock market may be entirely wrong.
Intuition tells us, and academic research confirms, that a company’s stock price should respond to important news and information. When a company announces a new product, for example, its stock should go up. And when results fall short of expectations, it should decline.
But a new paper titled “The Inefficient Pricing of News” calls this idea into question. The authors found that investors respond much more slowly and inconsistently to market news than previously thought.
EARLIER THIS SPRING, Emil Verner, an economist at MIT, made an observation: The stock market, he said, seemed to be exhibiting “excess tranquility.” Despite an ongoing war, inflation and other negative headlines, investors seemed surprisingly unfazed. The market was on track for its fourth year in a row of positive returns. Through May, it had gained 11%.
But no sooner did Verner make this observation that the market did begin to wobble. Last Friday,
A WHILE BACK, I was speaking with a fellow who had recently retired. He shared this observation, only half-jokingly: “Working was easy,” he said. What he meant was that financial management during our working years is more straightforward than it is in retirement. We earn and save and hope that our savings grow. But when we get to retirement, it becomes more complicated to know exactly how to manage those savings.
In the 1950s,
JONATHAN CLEMENTS’S final book was released this week. Titled Money and Me, it traces the arc of Jonathan’s nearly four-decade career as a personal finance columnist.
Money and Me starts with the story of a man named George Cope, who was a nineteenth century tobacco baron. At the time of his death in 1888, Cope was one of Britain’s richest men. But within just two generations, his fortune was gone.
ECONOMICS IS KNOWN as “the dismal science,” and perhaps for good reason. Oftentimes it can be abstract and overly academic. There are, however, certain economic concepts that can be helpful to individual investors. Below are two that I see as especially important.
When it comes to the government’s ability to control—or least influence—the economy, there are two main levers. The first is fiscal policy, which refers to Congress’s (as well as state and local governments’) ability to levy taxes and to spend money.
BACK IN 2010, at the Berkshire Hathaway annual meeting, a shareholder challenged Warren Buffett. Noting that shares of motorcycle maker Harley-Davidson had nearly tripled over the prior year, he asked Buffett why he had chosen to buy the company’s bonds rather than its stock. Buffett’s reply was a two-minute masterclass in how to think about investments. It’s worth walking through it point by point.
To start, Buffett acknowledged that hindsight can be cruel.
AN UNUSUAL STORY hit the news this week. GameStop, the struggling video game retailer, announced a bid to buy eBay. The offer was unexpected, but what surprised investors more was the economics of the proposed deal. eBay is many times larger than GameStop, making it difficult to understand how GameStop would be able to finance the acquisition.
GameStop has offered $56 billion for eBay, comprised of cash and stock. For the cash portion, according to its May 3 press release,
IN THE INVESTMENT world, May 1st is a notable day. It was on May 1, 1975 that the Securities and Exchange Commission deregulated the brokerage industry. For the 183 years prior to that, trading commissions on the New York Stock Exchange had been fixed at uniformly high rates. But when deregulation arrived, competition got going. That’s when discount brokers like Charles Schwab got rolling, and over time, May Day, as it’s now referred to,
IN 2020, ELECTRIC car maker Lucid Motors brought in revenue of $4 million. Five years later, sales had risen impressively, to more than $1 billion. In 2025 alone, sales grew 68%. That sounds like a success story, and through that lens, it is. And yet, over that same period, the company’s stock dropped more than 89%.
What happened?
A better question is: What didn’t happen? Despite growing sales, the company has struggled to turn a profit.
IT’S BEEN MORE than six years since Covid first entered our vocabulary. It goes without saying that investors have experienced a lot, and for better or worse, recent market events provide some useful lessons. The first has to do with the nature of the stock market.
What drives stock prices? Open a finance textbook, and the answer will be clear: The value of a stock should equal the sum of the company’s future profits.
RECENTLY, The Wall Street Journal ran a story about a new type of investment known as a digital stock token. For now, they aren’t available in the U.S., but they’re coming soon, so it’s worth taking a closer look.
What are stock tokens? At the most basic level, they’re a technology designed to make stock market investing quicker and easier than it is today. With tokens, trading won’t be limited to traditional business hours.
THERE’S BEEN DRAMA recently in a normally quiet corner of the market.
This story got its start back in 2015, when Warren Buffett helped to merge food makers Kraft and Heinz. At first, it looked like a smart idea. Through cost-cutting, the combined company was expected to save more than $1 billion in annual operating expenses.
“This is my kind of transaction,” Buffett said at the time, “uniting two world-class organizations and delivering shareholder value.
WHEN PAUL EHRLICH’S obituary appeared a few weeks ago, it came and went without much notice. But during his lifetime, he was enormously influential.
By training, Ehrlich was a biologist, but he was most well known for his 1968 book, The Population Bomb. It opened with this dire prediction: “The battle to feed all of humanity is over. In the 1970s and 1980s hundreds of millions of people will starve to death.”
In his writings and speeches over the years,
IN AN INTERVIEW a little while back, the technology investor Peter Thiel drew an uncomfortable comparison. Today’s frenzy around artificial intelligence, he said, parallels the tech stock bubble of the 1990s. To illustrate his point, Thiel pointed to Amazon.
By any measure, it’s been an extraordinary success. But, Thiel points out, it hasn’t been a straight line. At one point early on, Amazon shares lost more than 90% of their value.
“My suspicion is that that’s roughly where we are in AI.
LAST WEEK THE government released its monthly employment figures for February. The results weren’t great. Payrolls declined, and unemployment ticked up. These numbers square with other downbeat data, including a recent uptick in bankruptcy filings.
Another worry: Oil prices have been rising, a result of the conflict in the Middle East. That’s a concern because it could lead to a reacceleration of inflation. It could also dampen consumer spending because higher gas prices act like a tax on consumers,
A POPULAR JOKE about retirement is that it can be hard work. That’s because financial planning is like a jigsaw puzzle, and retirement often means rearranging the pieces.
In the past, I’ve discussed two key pieces of that puzzle: how to determine a sustainable portfolio withdrawal rate and how to decide on an effective asset allocation. But there’s one more piece of the puzzle to contend with: taxes. Especially if you’re planning to retire on the earlier side,
BEFORE ITS FAILURE in 2008, Lehman Brothers had been one of the most prominent investment firms in the United States. After 158 years in business, what caused it to collapse so suddenly? In a word: complexity.
Lehman had been involved in the securitization of mortgages, a process that resulted in taking something relatively simple—a home mortgage—and turning it into something much more complicated, thus obscuring its true risk level. That was the proximate cause for the firm’s failure.
LAST YEAR, an unusual story made the news: The University of Chicago was reportedly looking to sell an entity known as the Center for Research in Security Prices (CRSP). The story came and went quietly, but it’s worth pausing to understand it.
CRSP’s origins date back to the 1960s. Its initial goal was to build a database of historical stock prices. This is harder than it might seem. Before trading was computerized, stock prices were maintained on paper.
OVER THE PAST YEAR, a new term has entered the lexicon: “Sell America.” The idea is that investors are losing confidence in the U.S. economy due to persistent deficits and concerns about other policy choices. Owing to these fears, some investors are pulling money out of U.S. stocks and reallocating to international markets. Others are opting for gold and silver. The result: In 2025, for the first time in a long time, international stocks demonstrably outpaced domestic equities,
WHAT’S THE BEST way to manage your investments?
A new book titled Your Perfect Portfolio helps answer this question. I spoke this week with the author, Cullen Roche.
Adam Grossman: The title is Your Perfect Portfolio with an emphasis on your.
Cullen Roche: I was very intentional about saying “your perfect portfolio” because everyone’s different, everyone’s unique. So I wrote this book with the intent of studying lots of different strategies and styles.
LISTEN TO THE financial news, and you’ll often hear reference to “the VIX.” But what exactly is the VIX, and how important is it?
The VIX index is intended to be a measure of investor sentiment. For that reason, it’s often referred to as the market’s “fear gauge.” How can investor sentiment be measured? While the math is complex, it’s based on a straightforward principle: When investors get nervous, they look for ways to protect their portfolios and are sometimes even willing to pay for that protection.
ACCORDING TO THE World Happiness Report, Finland ranks as the happiest nation in the world, a title it’s held for eight years in a row.
Each time this report is updated, it makes the news for a day or two but then fades. That’s for good reason, I think. As much as Finland might be a nice place, it isn’t necessarily practical to suggest that anyone pick up and move.
The good news, though,
IN THE EARLY 1950S, journalist Walter Winchell popularized the term “frienemies” when he used it to describe the fraying relationship between the United States and the Soviet Union. Today, we’re seeing a similar dynamic in our relationship with China. This makes it an important topic for investors.
Not long ago, the relationship between the U.S. and China was strong and mutually beneficial. Over the past 25 years, trade between the two countries has multiplied.
WHAT WAS THE road to outstanding investment performance in 2025? For the first time in a long time, it wasn’t Apple, Amazon or Nvidia. It was gold. Delivering its best performance in 45 years, gold rose nearly 65%. Despite these impressive gains, however, I still don’t see gold as a great investment.
Why not?
The most fundamental problem, in my view, is that gold lacks intrinsic value. Unlike traditional investments such as stocks, bonds and real estate,
LOOKING TO UPDATE your financial plan for 2026? Below are ten strategies you might consider:
Gaining control
January is a good time to audit your investments. I’d start with this very basic step: If you have accounts at multiple brokerage firms, see if you can consolidate them. This won’t necessarily lead to better investment results, but if you have fewer accounts, it’ll be easier to monitor and to manage them. This might not seem like an important exercise,
IN THE WORLD of personal finance, some topics are serious—and others less so. Since it’s the holiday season, it seems appropriate to look back at some of the year’s less weighty stories.
Early delivery. The year started off on a positive note for an Alabama couple. Sha’Nya Bennett was in labor and on her way to the hospital when a snow squall rolled in, forcing her to pull over. The expecting mom ended up delivering in her car,
LOOKING FORWARD TO some downtime over the holidays? Below are some favorite new personal finance books and articles to consider for your reading list.
A Richer Retirement by William Bengen – Back in the 1990s, financial planner William Bengen developed what’s come to be known as the 4% rule. It’s a framework to help retirees determine a sustainable portfolio withdrawal rate. This year, Bengen updated and expanded his research. The most compelling addition: Bengen addresses the question of asset allocation.
EARLIER THIS WEEK, the Federal Reserve’s Open Market Committee met and decided to lower interest rates by a quarter-point. This immediately sparked a war of words.
At a press conference, Fed chair Jerome Powell took a swipe at the White House, blaming the president’s new tariff policies for an uptick in inflation.
President Trump wasted no time in responding. All year, he has been lobbying Fed officials to move rates lower. And while they have been taking steps in that direction,
CRITICS OF INDEX FUNDS are pursuing a new line of attack. Passive investing, they argue, is distorting market prices and creating an unhealthy bubble.
To be sure, the market today is expensive. The price-to-earnings (P/E) ratio of the S&P 500 stands at about 22. That’s substantially above its long-term average of about 16. Of more concern, that metric is approaching a level not seen since the market peak in 2000, just before stocks dropped 57%.
IN THE SUMMER of 1966, author John McPhee spent two weeks lying on a picnic table in his backyard. Why?
McPhee was suffering from writer’s block. As he described it, “I had assembled enough material to fill a silo, and now I had no idea what to do with it.”
Investors find themselves in a similar situation today. There’s no shortage of financial information around us. But that doesn’t make it easier to know what to do with it.
FOR DECADES, RESEARCHERS have been looking at the link between money and happiness. The findings? In short, it’s a mixed bag.
To be sure, there are ways that money can boost happiness, and below are some ideas to consider. But there are also obstacles to contend with. We’ll look first at the obstacles before turning to the recommendations.
The most significant challenge is the fact that—to a great extent—our happiness level is hard-wired into us.
IN APRIL 2005, art dealers Robert Simon and Alex Parish traveled to New Orleans to attend an auction. They were particularly interested in a work titled Salvator Mundi. The painting was in bad shape, having been neglected for years. But Simon and Parish ended up bidding on it and taking it home for $10,000.
After some restoration work, the pair succeeded in having it authenticated as a work of Leonardo da Vinci.
LAST WEEK, OPENAI founder Sam Altman sat down for an interview with venture capitalist Brad Gerstner and Microsoft CEO Satya Nadella. Both are investors in OpenAI, so it seemed like a friendly audience. But Gerstner posed a question that seemed to make Altman uncomfortable.
Since introducing ChatGPT three years ago, OpenAI has posted impressive growth, but Gerstner wondered whether the company was, nonetheless, getting ahead of itself.
“How can a company with $13 billion in revenues make $1.4 trillion of spend commitments?” Gerstner asked.

Comments
I once asked Jonathan the origin of the HumbleDollar name, and this is how he explained it: "I racked my brain for months trying to come up with a name for the site. It had to be something to do with money, and I wanted a word that would express my financial philosophy. Somewhere in the middle of the night, the words 'humble' and 'dollar' met in my brain. I got out of bed, it was 2:00 a.m., and I went to GoDaddy and banged in humbledollar.com, and it was available. And that’s how HumbleDollar was born."
Post: Why HumbleDollar?
Link to comment from September 22, 2026
Thank you. That 1996 article is terrific. No surprise that Jonathan was 30 years ahead of me in articulating these points!
Post: 2026 Financial Plan
Link to comment from January 4, 2026
Edmund, this is such an important topic. Often, finances are where signs of cognitive decline first appear -- e.g., missed bills. Sadly, some number of people inadvertently let their life insurance policies lapse each year after years, or even decades, of making payments. There's also a lot of elder financial abuse. It's great when older folks allow their adult children to be involved, if only as another set of eyes.
Post: Decision Frameworks
Link to comment from November 30, 2025
Thanks, David. I'll second that recommendation on "Thinking in Bets."
Post: Decision Frameworks
Link to comment from November 30, 2025
Thanks, Martin. I'm 100% with you on simplicity. It's a virtue in my general, I think, but especially when it comes to investments. It's an uphill battle, though, because Wall Street loves financial engineering and is very good at marketing their latest concoctions.
Post: Decision Frameworks
Link to comment from November 30, 2025
Very true. Organizing your thoughts is at least half the battle. When I was in school, I remember being most impressed by the kids who asked questions that I hadn't even thought of.
Post: Decision Frameworks
Link to comment from November 30, 2025
Thanks for sharing your story. I've seen this up close too. I think a key challenge is that you can spend all day analyzing an investment (as I once did myself), but since no one can see the future, it's still hard to get it right. In other words, a lot of people in wealth management are well-intentioned, but in many cases, they're trying to do something which is nearly impossible.
Post: Decision Frameworks
Link to comment from November 30, 2025
Thank you. The most well known proponent of frameworks was probably Charlie Munger. It's a great way to approach questions.
Post: Decision Frameworks
Link to comment from November 30, 2025
Agreed. I thought it was so meaningful that in Jonathan's last year, he continued to work on HumbleDollar because that was what made him happy. In other words, when he received his diagnosis, the fact that he didn't decide to do anything different was confirmation that he was already spending his time exactly as he wanted.
Post: Money, Happiness, and Choice
Link to comment from November 23, 2025
That's another area where the research is clear: Social media definitely contributes to unhappiness. Even people who don't observe the religious Sabbath have started to observe a digital sabbath when they put away their phones, and that seems like a nice idea.
Post: Money, Happiness, and Choice
Link to comment from November 23, 2025