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.

TWENTY-FIVE YEARS ago, I found myself quite unexpectedly spending a night in Reno, Nevada. Gambling was the obvious form of evening entertainment, but money was tight back then. A friend convinced me to splurge and spend $20 playing a slot machine. My measly 25- and 50-cent wagers kept me entertained for nearly an hour, but when I was down to my last few quarters, I bet them all on one final play.
The machine immediately lit up with a colorful array of flashing lights and I waited patiently for my winnings to start spilling out.

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.

IF WE’RE TO RETIRE in comfort, we need to be deadly serious about saving money for perhaps three decades. That leaves a little wiggle room: If our careers span four decades, we might have a decade or more when we can be a little less focused on making and saving money.
The question is, when should this “goof off” period be? Conventional wisdom has its answer: We should pursue our passions in our 20s,

WE DON’T PROMISE thinner thighs and harder abs here at HumbleDollar. But—unbeknownst to us—we could be the secret to your relationship success.
This revelation comes from an academic paper, “A Penny Saved Is a Partner Earned: The Romantic Appeal of Savers,” by Prof. Jenny G. Olson and Prof. Scott I. Rick, which is based on Olson’s dissertation research.
Conventional wisdom—and earlier academic work—suggest that, if men flaunt their wealth, they’re likely to have greater dating success.

IS FINANCIAL PLANNING a product or a process? In other words, is a financial plan a document that you can print, bind and put on your shelf—or is it an ongoing activity? This is something of a religious debate within the finance community.
Supporters of the “it’s a product” view are usually dyed-in-the-wool financial planners. Not surprisingly, they believe that financial planning should result in a physical plan—an exhaustive, detailed document that’s full of analysis and projections.

FINANCIAL FREEDOM is the ability to spend our days doing what we love—and, with any luck, it will come with age. As we amass more wealth, we should become less motivated by fears of layoffs and hopes of bigger paychecks. Instead, our motivation should come from within, because we are increasingly free to focus on the things we’re passionate about.
This, I believe, is one of the three pillars of a happy financial life: We have fewer money worries,

ON THE AFTERNOON of Sunday, Sept. 28, 1941, it was cool and damp in Philadelphia. Inside Shibe Park, where the hometown Athletics were suiting up to face the Red Sox, all eyes were on Boston’s 23-year-old slugger, Ted Williams. It was the last day of the regular season, and Williams’s average stood just a hair short of .400, at .39955.
According to baseball’s official rules, this would have rounded up to an even .400 in the record books,

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,

WHAT MATTERS IS WHAT we focus on. Forget the bad that has happened. Don’t dwell on the goals that remain elusive. Instead, if we’re striving for greater happiness, we should ponder the good in our lives.
This is a great moment to do just that: Most of us are surrounded by friends and family, we have time away from work—and the abundance offered by U.S. society is, in many households, epitomized by a flabbergasting pile of presents.