IN THE SUMMER of 1789, George Washington got into a dispute with his Postmaster General—a fellow named Ebenezer Hazard—and removed him from office.
Looking for a new profession, Hazard decided to start an insurance company. He called his new firm the Insurance Company of North America and specialized in providing life insurance to ship captains. The business was a perfect fit for the times and quickly prospered. Still, I’m sure that even Hazard would be surprised to see his company still in business more than two centuries later.

“THERE ARE TWO kinds of people in the world…” There are Republicans and Democrats. Right-brained and left-brained. Yankees fans and Red Sox fans. And, of course, Starbucks people and Dunkin’ Donuts people.
In Boston, where Dunkin’ was founded and where I live, this is a particularly strong theme. Dunkin’ people and Starbucks people see themselves as very different. Starbucks aficionados see it as a higher-quality experience and don’t mind paying for it. Meanwhile, Dunkin’ fans are proud of their frugality and think that the people over at Starbucks are overpaying.

IN HER BESTSELLING book Thinking in Bets, retired poker champion Annie Duke stresses an important point: As kids in school, it was regarded as a failure if we ever answered a question, “I don’t know.” But in the world outside the classroom, the only honest answer to many questions is, “I don’t know” or “I’m not sure.” This isn’t due to ignorance. Rather, it’s because, in many cases, the precise right answer simply isn’t knowable.

MY FATHER WAS AGE 19 and my mother was 11 when the Great Depression started. They were married in 1942 and I was born in late 1943. Their view of money matters was surely tempered by their life experience.
They had no investments to speak of and always kept what little money they had in a checking account. They would never borrow and didn’t know what a credit card was.
Many years ago, I convinced my mother to buy 75 shares of the company I worked for—a large utility.

IN SUMMER 2011, a rural Illinois man named Wayne Sabaj was in his backyard picking broccoli, when something caught his eye. Half buried in the dirt, he found a sealed nylon bag. Inside was $150,000 in cash. For Sabaj, who was unemployed and had, in his words, “spent my last $10 on cigarettes,” this was a godsend.
Though it remains a mystery who had buried this particular stash of money, these sorts of finds are not uncommon.

RISK IS ARGUABLY the most important financial topic. But which risks should we worry about? There are all kinds of contenders: recession, accelerating inflation, political upheaval, global conflicts, sharp market declines, individual company turmoil.
But I would argue that, as we each assess our personal finances, one risk trumps all of these—and that’s the risk that we have lousy career earnings and maybe even find ourselves without a paycheck. How come? It isn’t simply that we would likely struggle to pay the bills and service our debts.

WHEN WE MAKE financial decisions, we usually have a pretty good idea what we’re getting. But what are we giving up? That, I believe, is the crucial, unasked question.
Think about any financial choice, whether it’s the shoes we buy, the stock we purchase or the kids’ college degree we promise to pay for. All too often, these are snap decisions. Captivated by the bright shiny object in front of our eyes, we make an isolated choice—and fail to grapple with the bigger picture.

DEAR 18-YEAR-OLD Kristine: You’re about to embark on adult life, so I want to share some financial advice with you. You will do many things right—and a few things wrong—so listen closely.
You’ll be heading off to college soon. Even though many of your high school classmates will be attending four-year schools, you’ll be staying closer to home. The local community college will be a good choice, since you have absolutely no idea what you want to do with the rest of your life.

MRS. J. LIVED IN southeast Virginia and had purchased an eight-year-old truck at auction for her college-bound child. It turns out that the truck had spent its entire life in and around Rochester, New York, in the heart of the Rust Belt. Mrs. J. had been advised by her local garage that many of the exposed chassis components on her truck were covered in rust. Her neighbors’ cars did not exhibit this condition. She felt the truck was unsafe and that the vehicle’s manufacturer—my employer—owed her a solution.

IN A CLASSIC EPISODE of the sitcom 30 Rock, Tina Fey’s character, Liz Lemon, muses about the size of her nest egg: “I have money saved. Two years. Maybe four, if I cancel cable.”
Not worried about the size of your cable bill? In all likelihood, you’re fretting about one aspect of your financial life—and probably more than one. You might be wrestling with housing costs, student loans, the cost of putting your own children through school,

TO IMPROVE OUR behavior, we first need to realize we’re on the wrong path and then figure out the right way forward. Often, this isn’t especially difficult. If we have no savings, obviously we need to sock away some money. If we’re overweight, we should cut back on the calories. If we’re out of shape, we need to hit the gym.
Instead, the real problem is getting ourselves to act.

The contemplative side of our brain is fully aware we ought to eat and spend less,

MOST MONEY conversations, especially with financial advisors, orbit around the concept of increasing dollars.
When is it best to buy stocks? Answer: in a down economy. Reallocate money from bonds.
When is it best to buy bonds? Answer: in a thriving economy. Reallocate money from stocks.
When is it best to save? The answer invariably seems to be: always.
On the one hand, I embrace this concept. A chronic self-tither,

TO BE PRUDENT managers of our own money, we need to read the small print—but we also need to keep an eye on the big picture.
To that end, whenever we make a financial decision, we should ponder three key questions: What’s the tradeoff, does the choice make sense given our broader financial life, and will we feel as good about the decision tomorrow as we do today?
Trading Off. Suppose we remodel the bathroom,

I LIKE LEARNING from successful people. If you want to be good at something, why not hear from somebody who’s actually done it?
Back when it was first published, I read The Millionaire Next Door and became fascinated with these folks. Over the next couple of decades, I applied the book’s teachings and eventually reached millionaire status myself.
Along the way, I started writing about personal finance, combining my interest in millionaires with my passion for learning from experts.

MOST OF US WILL never be fabulously wealthy and we’ll never earn huge incomes. Self-help authors, get-rich-quick seminars and motivational speakers might try to convince us otherwise. But if we turn to these folks for assistance, they’re the ones who typically make heaps of money—at our expense.
Such hucksterism doesn’t just carry a short-term cost, however. It also causes us to think about our lives in the wrong way, leaving us with an unwarranted sense of failure and distracting us from the right path forward.