THE BEAR MARKET HAS now dragged on for 15 months—and no doubt plenty of anguished investors are second-guessing their allocation to stocks. But as for me, I grow more enthusiastic with every drop in the Dow Jones Industrial Average. In fact, I’d be happy to see the bear market last a few months longer, so I can finish fully funding various tax-advantaged accounts for 2023.
Not only are stocks better value than they were 15 months ago,

RETIREMENT IS LIFE’S most daunting financial puzzle, not least because many of the decisions we make are difficult or impossible to reverse. To make matters worse, we’re often making decisions we’ve never made before, so we have no real expertise.
What sort of decisions am I talking about? Here are 10 examples.
1. When should I quit work? Needless to say, this is the most important retirement decision. Once you quit the workforce,

A FEW MONTHS BACK, this site’s editor suggested I write an article about the “10 things I learned about money from four years traveling the globe.” I thought, hey, if someone wants to pay me $60 to write about travel, I’m in. I’m hoping he’ll next suggest I write an article about drinking bourbon.
Starting in September 2017, my wife and I traveled the world for four straight years. Travel can be wondrous. Filled with new tastes,

WE BUY ALL KINDS of investments and financial products. But what is it that you haven’t bought, do you have a good reason for not buying—or is there a gaping hole in your finances?
Below are some of the investments and financial products I’ve chosen not to own. The list, of course, isn’t comprehensive—and I didn’t bother to touch on financial products that are beyond the pale. Equity-indexed annuities, anyone? How about leveraged exchange-traded funds?

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,

IF YOU KICK AROUND Wall Street for long enough, you’ll witness all kinds of investment fads—special purpose acquisition companies, cryptocurrencies, meme stocks, to name just a few. Each bubble differs, but the eventual comeuppance always feels brutally familiar.
But there aren’t just fads among investments. There are also fads among investment concepts. But while naïve investors tend to get caught up in investment bubbles, it’s the brainy types who fall in love with investment concepts,

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,

MONEY IS OFTEN TIGHT for those in their 20s. Yes, that first “adult” job typically pays more than any previous job. Still, finding money to save and invest can be tough. After handling all the other big expenses of early adulthood—house, wedding, student loans—there just isn’t much money left over.
That’s my dilemma and one facing many others in their 20s. How can we make extra money without getting a second job? My fiancée and I focus on earning money just by living.

I ADMIRE SUPER-SAVERS. I really do.
You know who I’m talking about: Ordinary people making ordinary salaries who are somehow able to sock away half or more of their disposable income and who accumulate enough to step away from the working world long before the rest of us.
We hear about these people all the time on podcasts. The couple who banked $1 million over the course of a decade by scrimping and saving.

IN SEPTEMBER 2014, The Wall Street Journal published a column entitled “The Simple Secret to Building Wealth.” An early paragraph began thus: “Wealth is born of great savings habits.”
As I read along, I found myself not only agreeing, but also wondering if the author had secretly consulted with my wife prior to penning the column. The similarities between his suggestions and our savings habits were striking.
I wrote an email to the author—who,

I GRADUATED FROM college in 2007, shortly before the economy was brought to its knees by the Great Recession. I worked in asset management for Macerich (symbol: MAC), a publicly traded real estate investment trust. During the panic, the company’s share price plunged from $92 to $5.
There was fear in the markets. You might even say mass hysteria. Our executives were mostly miserable because their stock options were underwater. Waves of layoffs ensued.

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,

I’M AN 81-YEAR-OLD retired radiologist. Early in my medical career, I realized my stock broker was managing my account for his benefit, not mine. I fired him and took charge of managing my own investments.
Today, I have four granddaughters who are starting to invest. Over the years, as I learned more about personal finance, I put together a 130-page financial notebook. My granddaughters probably don’t want to read my lengthy notes, so I decided to put together a one-page summary.

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,

RETIREMENT PLANNING videos and books can be frustrating because of the conflicting advice from so-called experts. Often, these experts are outside the mainstream. They retired in their 30s, or saved 50% of their income, or claim to be living so frugally in retirement that they need to replace just half of their old salary.

I prefer to think more about average Americans facing the reality and challenges of planning for retirement in the real world.