I DON’T USUALLY FOLLOW the NFL. But this year, I’ve made an exception—because the current season offers a valuable lesson not just for football fans, but also for investors.
Teams devote huge amounts of time, energy and money to determining who’s the best quarterback for their team. Yet, this year, three quarterbacks are leading their teams when most experts, who get paid to evaluate talent, didn’t give them much of a chance.
Brock Purdy leads the San Francisco 49ers.

HOW DID I GET financially to where I am today, 15 years into retirement? It’s a good question—one that’s taken me a lifetime to answer.

I’ve been fortunate in a way that’s nearly impossible for Americans today. I worked for one company for nearly 50 years and I accumulated a traditional pension based on that service. In addition, during my last few years on the job, I was eligible for stock options, restricted stock awards and enhanced bonuses.

I STUDIED MATH AND statistics at university. When I mentioned my academic focus at parties, eyes would glaze over as fellow students looked for a way to extricate themselves from the conversation.
To lighten the mood, I’d say I was studying statistics to learn how to get rich in the stock market. In truth, I had no idea what I was talking about, but it sounded good and would often break the ice. Still,

WHEN MY WIFE AND I got married, she had a credit card with an outstanding balance. Back then, you could write off the interest on your tax return. Still, I hate debt and I paid off her balance. Ever since, she’s continued to maintain a separate credit card because I wanted her to have a credit history, so she could take out a loan on her own if I died. We’ve always paid off her monthly balance in full.

DURING MY FINAL NINE years with the Coast Guard, I was involved in decisions regarding search-and-rescue operations. We were almost always working with imperfect information. For three of those nine years, I was responsible for all missions in one section of the Great Lakes and, in my last year, I made the final decision on when to suspend search-and-rescue operations in an even larger area.
To lower risk, we often assumed the worst, and threw copious operational resources at the situation.

HOW MANY OF OUR adult financial habits are shaped by childhood experiences? My parents, who grew up during the Great Depression, weren’t fans of providing allowances for my sisters and me. My oldest sister, Gail, got no pocket money but remembers being offered a quarter to fill a grocery bag with dandelions pulled from the yard. Lynn, 10 years older than me, received a quarter a week for a short period.
My first allowance was also a quarter a week,

THERE’S AN IRONY IN the world of personal finance: The activity that’s the most entertaining—picking stocks—is also, according to the data, one of the most counterproductive. Meanwhile, making asset allocation decisions is more akin to watching paint dry, and yet—according to the data—that’s one of the most important decisions an investor can make.
Asset allocation refers to the split among your investments—how much you hold in stocks, for example, versus bonds or real estate.

I BELIEVE MANAGING money should be kept as simple as possible. That’s usually the route to lower costs, fewer mistakes and greater financial peace of mind. But, alas, three crucial areas of our financial life defy simplicity: health insurance, taxes and paying for college.
This is hardly an original insight. Folks have complained for decades about the maddening complexity involved with all three. All are ripe for a total revamp, but there’s no sign that’ll happen any time soon.

WHEN I WAS IN COLLEGE, I thought I had investing all figured out. I’d taken a handful of finance and portfolio management courses, I’d allocated real money for the University of North Florida’s student-managed fund, and I’d researched individual stocks, mutual funds, exchange-traded funds and even options.
But my confidence was crushed by a year of unsuccessful options trading when I was age 20. Nonetheless, through my 20s and into my 30s, I remained optimistic that I could earn handsome long-run returns by overweighting a few investment factors—such as smaller companies and value stocks—and by having plenty of foreign stock exposure.

I WAS FIRED OR LAID off 10 times during my career. Why did this happen so often? One reason: I made a decision that I’d never quit a job.
This position was formed during high school when I had a job parking cars at a local Chinese restaurant. I became friends with the guy who’d set up this deal with the restaurant’s owners. While the job was fun, I realized one night that the payment this guy received from the owners wasn’t being divided evenly among all the teenagers parking cars.

I SHIFTED TO WORKING part-time more than a year ago. It was a way to ease into retirement and give me time to explore new activities. My reduced work hours were also a way to experience life without the singular job focus that had defined my working years and, indeed, my identity.
My new part-time status was, of course, accompanied by a markedly shrunken paycheck. That allowed my wife and me to see what it was like to be without the guaranteed and steady income we’d relied upon for nearly three decades.

I DON’T KNOW THAT MY life has been all that different from that of others. Still, what’s happened to me has—I believe—been good preparation for retirement. Here are seven life lessons I learned on my journey from childhood through to my departure from the workforce just before my 70th birthday.
Lesson No. 1: Doing it yourself can save big money. My older brother got me interested in cars. This was the late 1950s and 1960s,

THERE’S A SAYING that “perception is reality,” meaning that what you believe is your reality, whether it’s true or not. Changing our perception isn’t easy. It takes effort, along with a willingness to discover and accept facts.
Many Americans’ perceptions are incorrect, leading them to make subpar financial decisions. Consider:

Social Security. Nobody stole the trust fund, it’s not going broke and, yes, it will be there for you.
Medicare. It’s not socialized medicine.

AFTER MY COLLEGE freshman year in engineering, I was hired for a part-time summer job by a civil engineering firm in my home town. The office was in an upscale building where a lot of respectable businesses were headquartered. The company had an impressive name. But after starting, I discovered it was just a one-man show. Mr. Jones was the owner. I became his sole employee.
Jones was probably in his mid-70s. He’d headed up his own company for decades.

HI CHRIS, IT’S BEEN 45 years since we broke up, we’re now both age 78, and I’m winding down. I wanted to touch base and catch you up, but mostly let you know that I often think back on our 11 years as husband and wife, and how much I value the time we spent together. Sometimes, that period of my life seems far in the past, but other times it’s right on my shoulder,