IMAGINE PUTTING your teenager behind a steering wheel to take a driving test without any prior preparation. The result is predictable—she would fail and you’d be lucky if she didn’t crash. Would you reprimand her for this result? Of course not.
So why is it that so many of us are merciless—both to ourselves and even our loved ones—when it comes to our investing blunders? You know what I’m talking about: putting money into a meme stock that subsequently cratered;

LAST AUGUST, I wrote about the retention bonuses I scored by simply initiating a transfer of assets from one brokerage firm to another. Back then, I said I’d wait six months and then try again to capture this free money.
This time around, one broker offered me a promotion simply to stay put, but two others wouldn’t. I did some quick Google searches and found offers elsewhere, so I initiated the transfers and collected those bonuses.

MANY OF THE WORLD’S religions view humility as an admirable trait to which we should all aspire. It’s frequently associated with poverty, as practiced by devout orders like Buddhist monks and the Sisters of Mercy. But when it comes to investing, humility can—ironically—make you significantly wealthier.

As documented by the behavioral finance research, overconfidence can lead to worse investment returns when investors presume, without justification, that they’re skilled at, say, picking market-beating stocks. The research on indexing versus active stock fund management overwhelmingly shows that,

TO BE AWARDED a triple-A credit rating was once a priority for some of the biggest and best-known U.S. companies. Only the financially strongest companies, organizations and governments can earn a triple-A rating.
The triple-A rating typically bestows the lowest borrowing rates and suggests the highest ability to repay bondholders. But the triple-A club has been shrinking over the past four decades. Apple recently became only the third current corporate member of this exclusive club.

I ONCE JOINED a book club led by an amazingly smart guy. We were reading a challenging book by Nassim Nicholas Taleb, the philosopher, investor and probabilities expert. Our discussion leader was a Chartered Financial Analyst who had solved one of the most enduring riddles at Vanguard Group, where I worked at the time.
For many years—decades, really—Vanguard hadn’t offered an international bond fund. Our founder, Jack Bogle, wasn’t a fan of international investing in general.

HI, MY NAME IS MIKE and I’m a stock picker. Actually, I stopped picking a few years ago after I hit rock bottom and finally realized I had a problem. But there’s no such thing as an ex-stock picker.
I still frequent Seeking Alpha, read the occasional Barron’s article and, every now and then, have the urge to buy an individual stock. I still occasionally fall off the wagon, but nothing like the ol’ days.

QUICK FINANCIAL scores can be thrilling. The idea of plopping down a few bucks to hit it big with a lottery ticket or the roulette wheel is alluring to many. Even folks who know the odds are stacked in favor of the house engage in these gambles.
That brings me to a recent M1 Finance survey of more than 2,000 investors. A particularly sobering stat involved alternative assets: 73% of those who described their situation as “struggling to survive financially” planned to invest in some form of alternative asset,

MY PORTFOLIO GAINED some 4% in 2021. While I certainly didn’t expect to match the S&P 500’s impressive 28.6% performance, I was surprised at how low my return actually was. This surprise is a lesson unto itself: We often overestimate our own performance.
There’s a number of reasons for my portfolio’s middling returns. First, I began 2021 with my stock allocation at around 40%. Bonds, cash, and gold and gold mining companies rounded out the rest of my portfolio.

BACK IN NOVEMBER, I wrote about using options to bet that shares of Peloton Interactive would decline. This was my first options trade. I purchased the put option when Peloton was trading in the low $50s. The option cost me $200, and it gave me the right to sell 100 shares at $35 per share in March 2022.
Since then, Peloton’s shares have indeed tumbled. It was recently announced that the stock will be booted from the Nasdaq-100 index,

CRYPTOCURRENCIES have come under selling pressure over the past few months. That might have some readers thinking about buying the dip in, say, bitcoin or ethereum. Those two cryptos, the largest by market capitalization, are off more than 30% from their all-time highs.
I’ve been dabbling in digital assets, but not in the way you might imagine. I put about 3% of my portfolio into stablecoins. Stablecoins differ from the well-known cryptocurrencies we often hear about.

COULD I BE WRONG about indexing?
Every investor soon learns that being wrong is a frequent malady, particularly on the day-to-day decisions of when to buy. Those minor errors are, as we also learn, part of the “game” of investing and are best ignored. But what if there’s evidence that conflicts with your longer-term thinking and expectations? What if evidence conflicts with your central beliefs?
I suspect it could happen to me.
After 60 years of experience and study of investing,

SELLING COVERED calls can sound like a winning investment strategy, especially to yield-hungry investors frustrated by today’s low interest rates. Wouldn’t you know it? There are exchange-traded funds (ETFs) designed to mimic the strategy.
For background, covered calls are a yield-enhancement play that involve selling call options against stocks that you own. The call option gives you extra income, but—during the life of the option—your gains are capped at the call option’s strike price.

JUST HOURS INTO the new year, I received an email from a concerned investor. His worry: the state of the market—the S&P 500, in particular. With hundreds of constituent companies, the S&P index has the veneer of broad diversification. But scratch the surface, and it seems to carry more risk than investors might like. The issue: It’s top heavy.

As a group, the top 10 companies in the S&P 500 account for more than 30% of its overall value.

TOO MUCH FREE TIME, coupled with easy access to the internet, create a problem for this retiree. I obsessively check my IRA at least once—and often several times—each day.
I retired two years early with an above-average Social Security payment and a decent state pension, but not a whole lot in my IRA, which is my only retirement savings. Experts say I need much more, but a job loss in my late 50s, and the inability to find an equivalent position in my field and at the same pay level,

ONE OF THE GREAT pleasures of having grown children is seeing them do things better than you ever did.
My son, who’s in his mid-20s, is already well beyond me in terms of investments. When I was his age, I was still bouncing around in grad school, living off teaching stipends and dreaming of one day being a novelist. I had no concept of what a mutual fund was, how to trade stocks and bonds,