I’VE BEEN CHALLENGED—by Mr. Clements, no less. Jonathan didn’t actually say it, but his challenge was to defend my unorthodox views on investing and retirement, and the actions I’ve taken as a result.

Some of my decisions will seem illogical to others. Some don’t maximize investment returns. Some are very conservative, others not so much.

I don’t like math. I don’t like details. I haven’t used a spreadsheet in 30 years. I focus on the big picture and long-term goals.

AS ALWAYS, DR. SEUSS said it best: “Oh, the places you’ll go and the people you’ll meet.”
In making this statement, the good doctor could have been talking about the benefits of volunteering. Since inheriting some money in 2011, I haven’t had to work multiple jobs, as I did in graduate school and during the three years that followed. From 2012 on, I’ve had mostly full-time work, leaving me with time to volunteer for causes I care about.

WHEN I WAS YOUNG, my parents converted our basement into an indoor playground for the neighborhood kids.
My friends could listen to Elvis belt out Hound Dog or croon Love Me Tender on the Seeburg jukebox. Some chose instead to light up the Bally pinball machine. Others would challenge my father to a game of pool. Meanwhile, my mother would create mini-pizzas for everyone, with a slice of Swiss cheese drenched in tomato sauce on half an English muffin.

WE’RE A SINGLE-INCOME family with five children, so the prospect of paying for college for all our kids is daunting, to say the least. Yes, our oldest is now in her second year of college. But we still have a long way to go before they’ve all crossed the finish line.
Our kids are ages 19, 17, 12, nine and six. We’ve been homeschooling them since the beginning, with a few brief exceptions, including one daughter in a Department of Defense high school in Korea for a year and another daughter in a private high school for two years.

MY WIFE NEEDED KNEE replacement surgery a few years ago. Her health plan, which was provided through the school district where she worked, was a preferred provider organization with a large network of doctors. After some research, my wife decided she wanted her operation done at New York City’s Hospital for Special Surgery.
I love hearing about people’s lives. I’ve long read biographies to learn how others gained their fame or fortune, hoping for pointers that would help me with my own life.

WHEN I WAS YOUNG, I felt immortal. We all did. It’s natural and likely hardwired into our brains. Such feelings of immortality have an evolutionary advantage, encouraging us to take the risks necessary to succeed.
When I planned for retirement, the notion of immortality was front and center. I consider myself in excellent health. I eat right. I’m not overweight. I stay active. I have a close circle of friends and an active social community from which to draw strength.

SOME 90% OF TAXPAYERS claim the standard deduction on their tax return. Thanks to 2017’s Tax Cuts and Jobs Act, today’s standard deduction is larger than the itemized deductions of most taxpayers, including those who previously itemized.
But my wife and I are among the 10% of taxpayers who have continued to itemize, including each of the five years since I retired in 2018. Despite the much higher standard deduction for married couples over age 65,

I HAD A REVELATION while shoveling snow earlier this year. When I was age 40 or so, digging out after a snowstorm was always an ordeal for me, even with the aid of a snowblower. I’d need to take frequent breaks and would be wiped out for the rest of the day. Multiple body aches would appear over the next 24 hours, and full recovery might take a few days.
But in January, at age 61,

I OFTEN READ ABOUT the difficulties people face after retiring—difficulties that have nothing to do with money. Loss of identity, depression and boredom are all mentioned. It takes serious planning beyond finances to retire, we’re told.

As an employee, I was a type-A personality. I worked seven days a week, in and out of the office. I worked on vacations. My job required me to work with the organization’s most senior executives.

If there was anyone set for a fall upon retiring,

IN MY ENGLISH CLASS in junior high school, we read a play called I Remember Mama. It was a story about a poor Norwegian immigrant family living in San Francisco in the early 1900s.
The mother ran the household while her husband went to work and the children went to school. The mother was in charge of the family’s finances. Any time a family member needed extra money, he or she would have to ask Mama for it.

MY FIRST DAY IN the investment industry was—unfortunately—not so great. On the morning of Sept. 15, 2008, the investment bank Lehman Brothers filed for bankruptcy, sending the stock market into a free fall. The rest of 2008 was equally ugly, with the S&P 500 losing 37% for the year. But that experience provided investors with a valuable lesson—about the power of recency bias.
Recency bias is the mind’s tendency to extrapolate. When things are terrible,

INVESTING IS MESSY. Get used to it.
In the financial markets, you’ll typically pay a high price for certainty. That price is paid in lower investment returns, and sometimes also in greater financial hassles. Yet I see investors paying that price again and again.
Consider equity-indexed annuities. Investors imagine they’re getting stock market returns without any downside risk. But in truth, what they’re buying is an overhyped investment that captures only a portion of the stock market’s gain,

ONE OF MY BIGGEST retirement surprises: how difficult it is to maintain a robust social network.
My wife and I decided last Thanksgiving to travel overseas. In the past, we would have spent the holiday with family and friends. But now, most are no longer near us—or with us.
My mother passed away about four years ago. Afterward, my sister and brother-in-law moved to Tennessee to be closer to their son. My cousin Barb and her husband moved to Florida to be near their daughter.

MY RETIREMENT finances today are based on actions I took over six-plus decades, starting at age 18. Early on, I tried my hand at picking stocks and beating the market—to my regret. As time went on, I became more sensible.
Want to avoid my mistakes? Here are 10 tips based on my lifetime of managing money:

Start saving as soon as you have cash—it might be from shoveling snow, raking leaves or loose change—and never stop.

THE SECOND HALF of life isn’t just a continuation of the first. Rather, it’s an opportunity for transformation, new adventures and deepening wisdom. As we navigate these years, understanding the five key stages of this journey can help us live more joyfully and meaningfully. What five stages? Here’s a look at each:
Phase 1: Pre-Rapture. This stage, typically between ages 45 and 60, is marked by a feeling of newfound freedom and independence.