Adam M. Grossman

LAST SUNDAY, I discussed six strategies that could help you avoid decisions you’ll regret. But what if it’s too late—and you’ve already made a financial choice that’s left you unhappy? Now what?
Below are six notions to help you manage, and hopefully minimize, your regret over past decisions:
1. Your imagined happy ending likely wouldn’t have happened. Back in 2004, I recall seeing an iPod for the first time. A co-worker had received one for Christmas.

LAST WEEK, I LEARNED the disappointing news that our next-door neighbors—possibly the nicest people in the world—have put their house on the market.
While I’m sorry to see them go, I understand their decision. With a growing family, they’re looking for more room. During the pandemic, in fact, many people are making changes of one sort or another. Will they be happy with their choices?
That brings me to a new project, developed by author Daniel Pink,

THE TRICKY THING about investing is that there’s no single “right” approach. In an earlier article, I described the approach I favor—what I call the five minds of the investor, which involves being part optimist, pessimist, analyst, economist and psychologist.
But there are many other ways to be successful: You might invest in real estate, or follow a quantitative investment strategy, or invest in private companies. There are plenty of people who do very well with these approaches.

THEY SAY A PICTURE is worth a thousand words. But what about a chart?
A few weeks back, I noted that the stock market had become unusually top-heavy, with just five companies—Alphabet (i.e. Google), Amazon, Apple, Facebook and Microsoft—accounting for 20% of the overall value of the S&P 500. A chart that appeared online last week illustrates the impact of that imbalance. What it showed, in a nutshell, is that the overall S&P 500 is around breakeven for the year,

IN RECENT WEEKS, I’ve focused on some of the growing risks in the financial system. In the stock market, there are day trading enthusiasts and their obliging brokers. In Washington, there’s a Federal Reserve that has served up a seemingly bottomless punch bowl of new money.
Result: Despite the current recession and 11% unemployment, the stock market is close to its pre-coronavirus all-time high, fueled in part by the Fed’s policies, which have driven income-starved investors to take greater risk.

LAST WEEK, I TALKED about some of the unsettling trends in the financial markets. In that article, I focused on the role of brokers and day traders, and noted that it takes two to tango. But it turns out the dance floor is quite a bit more crowded than that.
Yes, brokers and day traders are doing their part, but there’s another set of actors who are less visible but a whole lot more influential.

IN HER MOST RECENT book, former Secretary of State Madeleine Albright quotes Mussolini. “If you pluck a chicken one feather at a time,” he said, “no one will notice.”
Don’t worry, I’m not veering into political commentary. But when I heard this quote, it brought to mind what we’ve been seeing in the financial markets this year. Taken individually, there’s nothing that strikes me as a clear red flag. But taken together, the current environment looks a little bit like a chicken that—all of a sudden—seems to have lost a whole lot of feathers.

THIS PAST WEEK, I received an email from a reader—let’s call him Tom. He described his experience during this year’s unruly stock market. After the market dropped in February and March, he said, the stock side of his portfolio lost a lot of its value. He decided to rebalance—that is, to buy more stocks so his original asset allocation would be restored. That is just what I would have done. But the key question—always,

I CAME ACROSS a statistic so surprising it was hard to believe: During the recent market downturn, according to Fidelity Investments, approximately 15% of investors sold all of their stock holdings. And among investors age 65 and older, nearly a third sold all their stock market investments. It was a discouraging figure, meaning that large numbers of people had picked exactly the wrong time to abandon their investments.
Fortunately, the figures were corrected a few days later.

AS AN INDIVIDUAL investor, what’s the key to success? It’s a question I hear a lot, especially in volatile times like this.
The answer, I think, is that there isn’t just one key, but rather five. The most successful investors seem to be equal parts optimist, pessimist, analyst, economist and psychologist. Together, I call these the five minds of the investor. If you can develop and balance all five, that—I believe—is the key to investment success.

EVERY YEAR, WHEN spring rolls around, investment folks trot out a favorite catchphrase: “Sell in May and go away.” This is based on the idea that the stock market lags during the summer, as people go on vacation.
While it may sound hokey as an investment rule, it’s hardly the only one. There’s also the January effect, which says that stocks do better just after the new year. Its cousin, the January barometer, stipulates that the market will have a good year if it has a good January.

IF YOU HAVE A SURPLUS in your household budget, what’s the best use for it? Does it make more sense to pay down debt or to invest those extra funds? With interest rates at such low levels, this is a question I’ve been hearing with increasing frequency.
Suppose your mortgage rate is 3.5%. If you pay down that debt, it’s like earning 3.5%. By contrast, if you invested in the stock market, your annual return would be uncertain.

EARLIER THIS YEAR, before the coronavirus hit, my family visited an amusement park. Everyone had fun—except my nine-year-old, who complained about the injustice of the rigged “down the clown” game.
You have probably seen this sort of thing: You’re given a handful of baseballs. Then, standing from about 10 feet away, the challenge is to knock down as many mechanical clowns as possible for a chance to win a prize. It doesn’t appear difficult—you aren’t that far away and the clowns are tightly spaced—but most people walk away empty-handed.

CONVERSATIONS ON Twitter aren’t known for their civility. Still, it came as a surprise last week when, out of the blue, author Nassim Nicholas Taleb launched a broadside against investor Clifford Asness, calling his work “crap,” along with other insults.
Asness wasted no time firing back, calling Taleb “very wrong and clearly both nuts and a world class terrible person.”
From there, the insults escalated: nasty, overrated, unoriginal, illogical, pretentious, emetic. That last one I had to look up in the dictionary.

WITH EVERYTHING that’s been going on recently, one story that’s received less attention is the ongoing spat between the White House and the board of the Thrift Savings Plan (TSP). As of a few days ago, there had been a ceasefire in the debate, but it isn’t over. It’s worth understanding what’s at stake—because the underlying issue has been a recurring theme in the investment industry.
If you aren’t familiar with the TSP, it’s one of the retirement plans available to federal government workers.