DRIVING CROSSTOWN, my brother and I stopped at an onramp, where a man held a cardboard sign.
“Does anyone give these people money?” my brother asked, then immediately answered his own question by mentioning a friend who hands out bottles of water instead. “Anything helps,” read the man’s sign.
“Sure,” I said. “I’ve seen people pass $5 bills out the window.” A single dollar used to be enough for a panhandler to end his shift and shuffle off to the nearest mini-market.

I MOVED FROM LONDON to New York City in 1986, when I was age 23. That’s when my financial education truly began.
I’d previously studied economics for three years and spent a year writing about the international financial markets for Euromoney magazine. Still, I knew almost nothing about investing, insurance, homeownership and other topics crucial to managing a household’s finances.
I’ve learned a ton since, and the focus of that education keeps changing,

THERE ARE TWO TYPES of mistake I make: those that are unintentional and those where I should have known what would happen.
After an unintentional mistake, I’m perplexed by what went wrong. I might say to myself “I’ll never do that again” or perhaps “what the heck just happened?” These are genuine mistakes, and I try to learn from them.
By contrast, stupid mistakes are those that I should have known would occur. No matter how many college degrees we have or how many years on the job,

I’VE SPENT MUCH OF MY life trying to better understand the world, especially the financial world. But I wonder whether I should have spent more of that time trying to better understand myself.
Why do some financial situations scare us, while others leave us unperturbed? Why do we spend time and money in ways we later regret? Why do we find our bad habits so difficult to change? Why do we admire some folks,

IT’S SEVEN MONTHS since I received my terminal diagnosis. Cancer is now the reality that looms over each day, and it’s been a rocky road, though the latest abdomen scan suggests I’ll be around for a while longer.
Where’s my head at? Here are four questions I’ve been asking myself—questions, I suspect, that might also be interesting to those who aren’t facing a terminal diagnosis.
1. Am I afraid of dying? No,

WE SUFFER LOSSES throughout our life. During our youth, we might leave old chums behind when our family starts fresh in a new town or when we go away to college. Later, a job loss or a divorce could leave us drained both financially and emotionally. But for most of us, our senior years are when loss hits hardest.
Our body is often the first casualty, especially the face we see in the mirror each morning.

DURING A PROJECT meeting at my old employer, a member of our team was constantly raising questions without offering any solutions. Afterwards, the team leader commented, “This guy always thinks his cup is half empty. Nothing will ever satisfy him.”
We’ve all known such people. Is there anything wrong with their attitude? It depends. My boss told me during my first week, “Never be satisfied with the status quo. Find ways to improve everything.

MANAGING MONEY IS about managing risk. But which risks? We all have a different collection of financial worries, and that drives the investments we buy and the insurance we purchase.
Problem is, every choice we make comes with a tradeoff. If we seek to fend off one risk, we often open ourselves up to other dangers. Consider five such tradeoffs:
1. Dying young vs. living long. When should we claim Social Security?

THIS HAS BEEN A YEAR of living large in the Kerr household.
I just finished adding up the numbers for 2024, and between my son’s wedding in Colorado in June, my own wedding in October, our honeymoon afterward, a vacation to Key West, a new car for my new wife, and various long-overdue repairs to Rachael’s townhouse, I spent upwards of $60,000 on items I hadn’t budgeted for in 2024.
The tally doesn’t include the $9,000 I spent on a hot tub for the mountain house.

MY LIFE’S GOAL WAS to make money. I make no apologies for this. I’m not particularly gifted in this pursuit, but I did persevere.
I take satisfaction that I stuck to my goal despite all obstacles. There were many trips, falls, mistakes and failures along the way. I had to work hard and seek a new job each time my old employment ended. I set out to do something—and I did it.
That all changed when I retired.

THE WAVES AND WEATHER are always changing on the coast of Maine. Last summer, I paddled my canoe to a nearby island in the sun, and two hours later had to feel my way back through a fog that hid the mainland.
There are longer-term forces at play here, too. The black mussel beds I steered around as a child are all gone now. So is the sea grass that made a good hiding place for crabs.

BEFORE HE DIED LAST year at age 99, a friend asked Charlie Munger if he planned to leave his considerable wealth to his children. Wouldn’t it impact their work ethic, his friend asked?
“Of course, it will,” Munger replied. “But you still have to do it.”
“Why?” his friend asked.
“Because if you don’t give them the money, they’ll hate you.”
Few of us are billionaires. Still, I find Munger’s comment instructive. It illustrates a reality about personal finance: that the notion of a perfectly optimal answer to any financial question is just that—a notion.

I’VE BEEN HAVING DOUBTS about some of the financial decisions I’ve made. I don’t know if it has to do with age. They say you tend to lose confidence as you grow older. Life-altering events, such as the death of loved ones, health issues and retirement, can weigh heavily and sow doubt.
For instance, I’ve been thinking about whether I should have sold my condo in 2020, during the pandemic. If I’d kept it, it would be worth quite a bit today.

THOMAS JEFFERSON once said that eternal vigilance is the price of liberty, and the philosopher Socrates opined that the unexamined life isn’t worth living.
Although they were talking about political freedom and personal philosophy, respectively, Jefferson and Socrates could well have been discussing personal finance. One of the best ways to engage in financial vigilance and self-examination is to keep a daily financial journal.
I’ve kept a personal journal since I was 14 years old,

WHO’S YOUR FINANCIAL hero? This should be someone whose qualities and character lend themselves to emulation in your own financial life.
Let’s set some ground rules here for picking a financial hero. First, your hero probably shouldn’t be the usual suspect: Warren Buffett. While Buffett is certainly a very successful investor, the investment game that he’s playing is very different from the one most of the rest of us are.
The same goes for folks like Elon Musk,