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I WROTE AN ARTICLE last month about five financial lessons I learned at Ringling Bros. and Barnum & Bailey’s Clown College. But Clown College didn’t just offer financial lessons—it also offered valuable life lessons.
It was a topic I used to discuss with my students. For the last 16 years of my career, I taught college accounting courses. I encouraged the students to lead lives of reflection and learn from their experiences. I would share a short PowerPoint presentation,

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,

RINGLING BROS. and Barnum & Bailey Circus operated Clown College from 1969 to 1997. I attended in fall 1978 in Venice, Florida, home of Ringling’s winter quarters. Clown College was a one-semester, tuition-free, rigorous training program in clowning.
After completing General Electric’s two-year financial management program, I wanted to do something different. I applied to both the Wharton MBA program and Clown College. To my surprise, I was accepted by both. The decision was easy.

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).

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,

DURING A RECENT vacation, my son Max and I played Monopoly. I was amazed at all the personal finance lessons you can learn from the game—one that was first produced in 1935.
We played by the actual Monopoly rules. That includes not getting money just by landing on Free Parking. It also means not auctioning off properties if the person landing on them decides not to pay the list price.

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,

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.

LET’S NOT CALL THEM resolutions because that imposes a sense of obligation. Rather, think of these as adjustments that could give you—and maybe your kids—a smoother ride in 2022:

Check the beneficiaries on your employer’s retirement plan, IRAs and life insurance policies. Sometimes money winds up with an ex-spouse or maybe a younger child gets left off the list. This is an easy fix—while you’re alive. After that, it’s a mess.
How much do you pay for your investments—in dollars,

I WAS AN AIRLINE pilot for 42 years before retiring about a year ago. Traveling was the job and, of course, the opportunity to fly free on days off was a big deal. That meant more traveling. Now retired with kids and grandkids scattered around the country, my lovely bride and I continue to fly regularly.
Planning your next trip? Here are nine tips to make the inevitably stressful experience a little better:

Never book a trip with connecting flights unless it’s absolutely necessary.

READERS HAVE CAST an eye on more than 13 million HumbleDollar pages over the past five years. Not surprisingly, many of those pageviews were garnered by the homepage, the latest articles page and the main money guide page. But what about the site’s articles? Here are the 30 best-read pieces since the site’s launch on Dec. 31, 2016:

Terms of the Trade (2019) by Jim Wasserman
Nobody Told Me (2020) by Jonathan Clements
Farewell Money (2019) by Richard Quinn
He Gets,

WHAT SEEMS OBVIOUS isn’t always true. Here are seven examples from the financial world:

Just because an investment has performed well doesn’t mean that’s a good guide to the future. This is usually mentioned with regard to stocks. But today, my bigger concern is folks who are extrapolating past bond fund returns. Their strong past performance was driven by a huge drop in interest rates over the past four decades—something that can’t be repeated starting from 2021’s tiny yields.

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.