ON MONDAY, MAY 2, I logged onto my Chase bank account—and discovered my balance was $992.43, many thousands of dollars less than I expected. My first thought: I’m going to get hit with a low-balance fee.
That, alas, should have been the least of my worries.
I clicked through to see the account details, and discovered that check No. 1126 had been made out to Milton Cherry for $7,000. But none of the writing on the check was mine,

WHAT SEEMS TRUE about money often turns out to be false. That brings me to the financial paradoxes I’ve come across during my investing journey. Here are my top 12:

The more we try to trade our way to profits, the less likely we are to profit.
The more boring an investment—think index funds—the more exciting the long-run performance will probably be.
The more exciting an investment—name your latest Wall Street concoction, SPAC or anything crypto—the less exciting the long-term results typically are.

HALF OF THE COLLEGE students I taught last semester just graduated. A few are going on to graduate school, but most are starting accounting, finance or other business careers. For my classes with a heavy concentration of seniors, I reserve the last five minutes of the final class to give them a few career tips. In keeping with my overall teaching approach, I keep the message simple: Do what you enjoy.
Now, this isn’t the usual “follow your passion” pitch you hear in so many commencement addresses.

WHEN WE AIM FOR financial independence, what we’re usually trying to do is to convert our current work time into future free time. We exchange our time and labor for money today. The wealth we accumulate then buys us a future that’s free from labor.
Given this exchange of labor for future freedom, what’s the most efficient way to speed our progress? According to a research paper, “Capitalists in the 21st Century,” the best strategy is to own a business.

I WAS PLEASANTLY surprised recently when a lump-sum dividend payment showed up in my brokerage account. It was from a preferred stock I bought a few years ago to boost my investment income. The windfall reminded me of the three criteria I’d used to screen preferred shares:

Taxation. Unlike bond payments, which are taxed as ordinary income, the income payments from most—but not all—preferred stocks enjoy the favorable tax treatment given to qualified dividends.

WHEN I WAS IN COLLEGE, late in the evening and usually after a few drinks, someone would often play Edith Piaf’s Non, Je Ne Regrette Rien, her stirring and defiant 1960 song about regretting nothing.
It’s a sentiment worth recalling as we look back on our financial life. Here are four things we shouldn’t regret:
Saving too much. Is that really something to regret? It’s undoubtedly better than the alternative: saving too little.

LAST MONTH MARKED 40 years of wedded bliss for my wife and me. I’m amazed at how fast the time has gone. I still remember the day we met. It was at a party celebrating her high school graduation. I gave her a ride to pick up a pack of cigarettes, all the while lecturing her on the dangers of smoking. I believe I saved her from a lifetime of smoking. She saved me from everything else.

LIKE MILLIONS OF other Americans, I’m experiencing serious sticker shock when I gas up the car.
Last week, I was filling up my 2019 Ford F-150 and, for the first time ever, the bill topped $100. That was 21 gallons of regular unleaded at $4.85 a gallon.
Shelling out that kind of cash for a tankful of gas is hard enough for working folks. But for those of us who are retired and living on a set income,

YOU MIGHT WANT TO check your mailbox. Mr. Market has been sending around a book of discount coupons on some great index funds and individual stocks.
Twenty-two percent off the S&P 500’s closing high set earlier this year. Seventeen percent off the Dow Jones Industrial Average. How about a whopping 33% off the Nasdaq Composite?
Still kicking yourself for not scooping up Amazon’s stock (symbol: AMZN) in early 2020 when it was—adjusted for the recent stock split—below $100?

MY WIFE AND I RECENTLY took advantage of one of the most valuable tax breaks for the typical American family. The tax code provides a generous exemption on the profit from the sale of a primary home. Although this is widely known, it also—based on my conversations with a variety of people—seems to be widely misunderstood.
The Taxpayer Relief Act of 1997 made a major change to the taxation of home sales. Prior to this,

CONSUMERS’ MOOD HAS never been worse—at least according to the University of Michigan Consumer Sentiment Index. The monthly survey, released last Friday morning, paralleled the worse-than-expected Consumer Price Index report. May’s inflation reading notched a fresh four-decade high as Americans—and the rest of the world—grapple with soaring food and energy costs. The issue is front and center, and we all feel it every day.
The hits keep on coming. This weekend, AAA confirmed a grim milestone: The average price of a gallon of regular gas topped $5.

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,

FOR THE FIRST TIME, retail investors have more money in index funds than actively managed funds. This is based on March 31 figures compiled by Morningstar and reported by columnist Allan Sloan.
Twenty-five years ago, Vanguard Group founder Jack Bogle published his remembrance of the 1970s launch of the first index fund geared to main street investors. As I page through the book again, I’m reminded of how close indexing came to failing.
Bogle recounts going on a 12-city roadshow,

EACH OF US TAKES our monthly income and then makes countless decisions—some big, some small—about how to use those dollars. How can we get the most from the money that flows through our hands? I find it helpful to look at this “income allocation” through three prisms.
Divvying it up. We can use our income for three main purposes: spending it today, saving it for tomorrow or giving it to others. Our instinct is to spend today,

I GREW UP IN a lower-middle-class family. We lived in a small apartment where I slept on the living room couch. My father sold cars for a living.

Today, my living standard is quite different. On average, 97% of retirees my age have less income and assets than my wife and me. Our friends are in similar economic circumstances. If they weren’t, they couldn’t live where we do.

The minimum needed to live in our condo community is $24,000 a year.