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.

INFLATION HAS BEEN the big economic story of 2022. Steep increases in consumer prices have hurt families in many ways—some of which aren’t so obvious.
You’re likely aware of the hefty increases in borrowing costs, home prices, rents, gas prices and groceries. But here’s something else to consider: how inflation can lead to higher taxes.
Important parts of the federal tax code aren’t indexed for inflation. Result: If inflation leads to nominal increases in a family’s income,

DURING MY NEARLY 70 trips around the sun, I have made countless mistakes. Most have been minor, but three stand out. Two I have already made, and the third I’m about to make.
Mistake No. 1: Go-Kart. When I was 12 years old, I bought a go-kart. It has a fiberglass body and was built to resemble the car driven to victory by legendary driver Jim Clark in the 1965 Indianapolis 500.

THE MOST POWERFUL financial ideas are those that help us make better money decisions—by providing a lens through which to understand ourselves and the world around us. Examples? Think about notions like loss aversion, diversification and market efficiency, all ideas frequently mentioned in HumbleDollar articles. Every investor, I believe, should understand such concepts.
To that list of key ideas, I’d favor adding five others—all underappreciated, I’d argue, but all central to how I think about the financial world.

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.

THE LONGER WE LIVE, the more perspective we have—and the more foolish many of our earlier beliefs seem. We start our adult journey confident that we’ll make our mark on the world and that the financial rewards we collect will greatly enhance our life. By the time we reach retirement, things look quite different. Here are five things I’ve learned along the way:
1. Fame is fleeting. How many entertainers, sports stars and politicians have each of us forgotten?

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.

EVEN THOUGH I’M NOT a doctor, I’ve been around medicine all my life. My father was a general practitioner and I spent my career in hospital administration. I had administrative oversight over three emergency departments of varying sizes. Based on my experience, here are 10 recommendations that may improve your experience should you need to visit an emergency room:
1. If you use the emergency room (ER) for a non-acute medical condition, bring a book.

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%.

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.

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.

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,

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,

I JUST COMPLETED my fourth year preparing tax returns as part of the federal government’s Volunteer Income Tax Assistance (VITA) program. I’ve seen first-hand how confusing our tax code can be for many taxpayers. Here are the 10 areas of confusion I’ve encountered most often:
1. Income. Anyone looking through a tax return will see multiple definitions of income. There’s total income, adjusted gross income (AGI), modified adjusted gross income, provisional income and taxable income.

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.