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.

“BUYING THE DIP.” It’s a phrase often uttered with contempt by Wall Street strategists and money managers, who look down their nose at everyday investors who instinctively shovel more money into stocks simply because share prices have fallen.
Commentators “caution against” it, dismiss it as “not an investment strategy,” predict it’s going to “die,” argue it could get “very, very nasty” and contend that—when everyday investors buy on dips—it’s a “contrarian signal.” And I got all that based on a quick internet search.

YEARS AGO, WHEN THE kids were teenagers, single Dad here was cooking dinner. You guessed it, hot dogs.
I skillfully picked one up from the hot pan with my fingers and tossed it in a bun.
When my daughter began to imitate me, I nearly shrieked. She lacked my years of experience in gauging exactly how hot the sides of the dog would be, how far from the splattering grease I needed to position my fingers,

IF YOU’VE WORKED a lifetime—while prudently saving and investing—so that in old age you’re well off financially, should you feel guilty?
If your retirement income is greater than the income of most American families, including those still raising young children and facing college costs, as well as the cost of their own retirement, is that embarrassing?
A few years back, during a discussion about how people spend, save and invest, my son-in-law—who’s a financial advisor to high net worth families—casually said to me,

IT’S INDEPENDENCE Day. But how truly independent are we, both financially and in our thinking? The two, I believe, are inextricably entwined.
Whether it’s the TV shows we watch, the political views we hold or the investments we buy, we often take our cues from family, friends and colleagues. They, in turn, may be influenced by advertising and the media. But however ideas get spread, the result is that most of us aren’t the fiercely independent thinkers we imagine.

I’M 28 YEARS OLD. How much should I have in stocks? Some financial experts would suggest allocating 90% of my portfolio, because I have a long time horizon and a steady job. But I don’t think that would be a good idea for me.
My father has driven hundreds of thousands of kilometers over his lifetime—because he’s afraid of flying, despite the much lower risk that air travel entails. Similarly, I have a good idea of what optimal investing behavior looks like for someone of my age.

MAKING CHANGES TO our everyday behavior isn’t easy. Inertia is a powerful force: Our brains tend to be on autopilot, not thinking much about what we’re doing—or why we’re doing it. It’s time-consuming and takes effort to pause and reflect on our habits and behavior.
Like so many others around the world, I found myself in lockdown earlier this year. I took advantage of the time to reassess my finances. I was shocked by some of the spending patterns I spotted,

WE ALL WANT THE GOOD life, though we’d likely differ on what exactly that is. Still, our wish list might include things like meaningful work, a robust network of friends and family, minimal money worries, service to others, good health, a long life, and a sense of both serenity and purpose.
What stands in our way? As we strive to make the most of the limited time we’re given, it’s worth pondering how we’re constrained and what we can do to improve our lot.

MONEY IS ONE OF THE most emotional issues we deal with. It can create both immense stress and moments of pleasure. I’m guessing the way each of us view money, and how we handle it, is as unique as our fingerprints.
My wife’s car of 14 years was kaput and headed for the junkyard. Fixing the wiring and computer on her 2006 Jaguar would have cost $5,000—far more than the car was worth, even though it was otherwise in very good shape.

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.

I LOVE BOOKS BY Bill Bryson. If you haven’t read his latest, The Body: A Guide for Occupants, you should.
It’s an encyclopedia of the wonders of the human body. The overriding message, jumping out of every page, is how truly miraculous our bodies are.
Did you know, for example, that you are made of seven billion billion billion atoms? That if you laid all the DNA in your body end to end it would stretch 10 billion miles,

HUMANS ARE WIRED in ways that, alas, aren’t conducive to achieving our financial goals. Indeed, thanks to research by academics focused on behavioral finance, we now have a much better handle on the money mistakes that many of us regularly make. Want to become a better investor? Here are three insights into ourselves, compliments of behavioral finance:
The illusion of understanding. Once you’re aware of this illusion, you start seeing it everywhere,

DOES OUR PERSONALITY help determine our financial success? It seems it does, or so says academic research.
Psychologists have zeroed in on five key personality traits: extraversion, conscientiousness, agreeableness, neuroticism and openness to experiences. Think of each trait as a spectrum from, say, very conscientious to not at all. Each of us sits somewhere on the five spectrums. Maybe we’re a bit of an extravert, somewhat inclined toward neuroticism, and extremely open to new experiences and ideas.

MANY INVESTORS endured their first stock market crash this year. But what if you’ve never before invested in stocks? How do you know what your risk tolerance is—and how do you keep yourself calm?
There are no easy answers. Questionnaires aren’t a great way to find out our risk tolerance. They ask us about hypotheticals when we’re calm, but we act and think differently when the storm hits. Instead, the only sure way to find out our risk tolerance is to weather a storm or two.

“TAKE FIVE” IS JAZZ great Dave Brubeck’s most popular and enduring number—but it’s also a darn good piece of decision-making advice.
A few weeks ago, my son was struggling with exams and papers ahead of his graduation from the University of Pennsylvania. Though he would go on to graduate magna cum laude, he was in a dark place. I said, “Imagine a time two weeks from now when you’re back home and can relax,