PUBLIC SPEAKING WAS my nemesis throughout my academic career. Though I found it frightening, I’d always been able to tough my way through the lectures and avoid a full-blown anxiety attack. Then, during a theories of psychotherapy seminar for psychiatry residents, the panic broke through.
Though only my first diagnosable episode, it portended an affliction far more sinister. It was a premorbid symptom of an underlying depression that would topple my career, derail my investment ambitions,

“I DON’T LIKE BEING too much of an example for people who just want to make money. If you wrest a fortune from life by buying little pieces of paper, I don’t think that’s enough. I never consider it enough of a life to merely be shrewd at picking stocks. If you’re good at just investing your own money, I hope you’ll be good at something more.”
What Charlie Munger, the vice chairman of Berkshire Hathaway,

“IT DOESN’T MATTER IF our planned trips might jeopardize our retirement savings.” The word “jeopardize” was spoken with a sarcastic tone.
It was clear my two financial-planning clients didn’t appreciate my message. They were adamant. Their 10 pricey National Geographic trips, which would span the globe, must remain on their bucket list.
So began a challenging chat. Based on their excitement about their retirement wish list, it would have been easier to simply applaud their exotic plans.

I SPOKE RECENTLY with a fellow who had climbed Mount Everest. The first question I asked: What was it like at the top?
What I expected him to say was that the view was dramatic. Instead, he said, his time at the summit turned out to be less than he’d expected. For starters, it was 4:45 a.m., so there wasn’t a lot of visibility. In addition, it was minus 45 degrees. Because of that,

MONEY BUYS HAPPINESS—but it may not buy us very much. Indeed, no matter how much we earn and no matter what other steps we take to boost happiness, we may discover the impact is modest and fleeting.
That brings me to a recent academic debate. In 2010, Princeton University’s Angus Deaton and Daniel Kahneman noted that happiness, on average, didn’t appear to increase beyond an annual income of $75,000 or so—a finding that’s since been widely reported in the mainstream media.

AS A TEENAGER, I wanted to be an architect. I took six years of mechanical drawing during junior and senior high school, and I was good at it, earning nearly all As.

At another time, in my 30s, I thought about becoming a lawyer. People told me I’d make a good one. A lawyer’s opinion seemed to carry more weight, even when the subject was unrelated to legal matters.

I also wanted to play a musical instrument.

I SPENT NINE YEARS at English boarding schools. The food was beyond disgusting. The buildings were cold and drafty. I was constantly bullied. I would go as long as 14 weeks at a time without seeing my parents, who were based first in Bangladesh and then Washington, D.C.
But I also knew I was getting a good education, and I opted to stay when I had the chance to return home and go to the local U.S.

AT AGE 55, I’M PERHAPS a bit young to spend time reflecting on my life. My maternal grandmother died at 101, so I could have many more decades to go. Nevertheless, I find myself more nostalgic now than I was just a few years ago.
I often think back to my childhood and how it shaped who I am today. In 1976, when I was in fourth grade, my parents purchased a two-and-a-half-acre property in a small town outside of Eugene,

MANY OF THE WEALTHY people I’ve studied were extremely frugal—to the point of eccentricity. Why is it that when rich folks are tightfisted, people call them eccentric, but—if you aren’t rich—people tag you as cheap?
New Jersey Bell Telephone Co., now called Verizon, used to have small inserts with its bills that highlighted persons of note who had a connection to the state, whether they were natives or had resided there at some point,

EVEN IN OUR consumer-driven society, some things are looked down upon if bought. One of those things is companionship.
I’ll leave the topic of sexual intimacy for another day. What I’m talking about here is paying—directly or indirectly—for social interaction. We might buy a younger colleague lunch simply to have somebody to dine with. We might continue therapy long after we’ve finished exploring the issues that prompted us to sign up. We all have a need to connect with others and thereby have our own existence validated.

IN OLD ENGLISH, to be “ready” for something meant to be well counseled. The English King Aethelred the Unready earned his nickname because he was ill-advised. His tumultuous reign ended with invasions and revolts, including one by his son.
When we feel we have “extra” money or even just a hankering to spend, there’s a host of outside voices to counsel us. Most try to influence our actions out of self-interest—for their commercial benefit.

HOW WE SPEND DEPENDS on how we feel about money.
To be sure, we’re supposed to spend according to our financial situation and needs. But life experiences can so badly distort our attitude toward money that our financial decisions end up being ruled by fear and insecurity rather than questions of affordability. Such is the case with an acquaintance—let’s call her Satee—whose money habits are at odds with her financial standing.
Satee grew up in a typical Indian family of four.

I RECENTLY HAD a revelation about my adult children: When it comes to money, they’re a lot like me—and that’s both a good thing and a bad thing.

I had this revelation while dining with my 25-year-old son at a sports bar over the New Year’s holiday. The food was marginal—it was a sports bar, after all—but the plates came loaded with food. What’s more, the prices were quite reasonable, especially compared to those in Philadelphia and Washington,

MY FATHER RETIRED from a 35-year teaching career in 2002, when he was 56 years old. He hasn’t worked a day since. For years, his retirement was the primary model for my retirement aspirations—until I realized my path needed to diverge.
Like many dads, he worked a career he tolerated but probably didn’t love. It provided our family with a comfortable lifestyle in the suburbs of a low-cost-of-living city. Teaching enabled him to be ever-present during my youth,

IN JANUARY 1987, I was an unmarried junior Coast Guard officer just beginning the flight stage of U.S. Navy flying training. I decided to see a financial advisor who’d been recommended by friends.
This wasn’t just any advisor, but rather a retired Air Force lieutenant colonel and fighter pilot. He worked for a firm whose advisors were comprised mostly of retired military officers, and they marketed their services primarily to military officers. If there was anyone I could trust,