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.

PAUL NEWMAN WAS BEST known as an actor, but he was also passionate about auto racing. He took his hobby seriously, improved his driving skills and won many races, including on his “home track” at Lime Rock, Connecticut.
His wife, actress Joanne Woodward, supported her husband’s auto racing career, but also worried about him. She bought him a Rolex watch to wear when he raced. To personalize the gift, she had an inscription added to the back.

A FEW MONTHS AGO, my wife and I were searching for an exciting diversion on a Saturday evening. It didn’t take long to agree on the perfect experience—logging onto SSA.gov to check out our estimated Social Security benefits.
What’s so thrilling about that? Like many people, Social Security will comprise a key component of our retirement income. Even now, those future funds exert a strong influence on our plans.
Background. I’ll turn age 62 this month and still work full-time.

FOR A FEW YEARS early in my career, I was an internal revenue agent for the IRS. I audited the tax returns of small businessmen, drug dealers, doctors, lawyers, a professional basketball player and everybody in between.
That was 43 years ago, when the IRS was much bigger relative to the population. One result: A larger percentage of the population were subjected to audits.
I saw and heard a lot. Some people would put dogs,

MOST READERS HAVE likely graduated from the vacations of their youth, where they saved a few dollars by sleeping on a friend’s hand-me-down couch. Still, some of my fondest travel memories were shaped by such frugal accommodation.
I once traveled cross-country on a summer camp trip with 48 other teens, touring the greater U.S. in a converted Greyhound bus. It was an eye-opener, visiting such heralded landmarks as the Statue of Liberty and the St.

I RECENTLY STUMBLED on a retirement planning blog listing the top 10 regrets of retirees. Planning for health care costs was among the things that people wish they’d handled differently.
The site had this suggestion: “Before you retire, you should get a reasonable estimate of your health care costs and make sure you can afford them. Medicare does not cover everything and most people spend hundreds of thousands of dollars in out-of-pocket health care expenses in retirement—not even including funding a long-term-care need.”
This statement is scary—and very misleading.