THE PROLIFIC MR. QUINN recently wrote that people who were irresponsible in one area of their life, such as failing to return shopping carts, also tend to be irresponsible in other areas, like managing their finances. He’s probably right. Still, I’ve had times when, even though I’m a “responsible person”—I’ve had a successful career, my kids lived to grow up, and so forth—I nonetheless had pockets of disorder in my life.
For me, the two biggest areas of chaos were managing money and maintaining a healthy diet and exercise regimen.

AS I WROTE THIS STORY, the word count kept climbing and climbing because it has more twists and turns than a detective novel. It was so long I was afraid no one would read it, not even my mother. So, here is a condensed version of what I wanted to say.
The hardest transition for some folks as they reach retirement is to go from a saver to a spender of what they’ve saved.

PEOPLE WHO INVEST in the stock market and people who bet on horses both hope to win. I expected the efficiency and behavioral finance factors that rule the stock market to have similar effects on horse betting. Instead, I found just the opposite.
The story begins 40 years ago. A few years after we were married, I suggested to my wife that we spend a day at the fabled Saratoga Race Course in Upstate New York and watch the thoroughbreds run.

A WHILE BACK, I WAS speaking with a mutual fund manager. In describing one of his fund’s stocks, he noted, “I owned it for a while, then I sold it, but then I bought it back.” It was a surprising comment since frequent trading is, in most cases, unproductive. Indeed, Warren Buffett has often said that his preferred holding period for an investment is “forever,” and many see that long-term mindset as crucial to his success.

THE DOUBLE-DIGIT recovery by the S&P 500-stock index this year has been driven almost entirely by seven mega-cap stocks: Apple, Google, Microsoft, Amazon, Meta, Tesla and Nvidia. In fact, these seven stocks now comprise more than 25% of the index.
Since our family is heavily invested in a mix of the S&P 500, U.S. technology and growth funds, plus some individual tech stocks, I began to worry about our portfolio’s investment concentration. I tallied our positions in these seven stocks across all our accounts.

DON’T ASSUME YOUR PATH up the mountain is one that everybody else should also follow.
I don’t budget, I earmark 80% of my retirement savings for stocks and I’m currently well above that level, I don’t have a separate emergency fund, I expect to live comfortably in retirement on half of what I currently earn, I plan to delay Social Security until age 70 and my stock market money is entirely in index funds,

MY WIFE IS OUT OF town for a while, so I have a lot of free time on my hands. I asked Carl, an old schoolmate, if he’d like to have lunch. I thought it would be a chance to give Carl a couple of copies of the HumbleDollar book, My Money Journey.
I didn’t think Carl would actually read the essay I wrote, let alone the whole book.

I NEVER SAW THE NEED to buy prescriptions from anywhere other than the local pharmacy until—for reasons that still aren’t clear—a medication I’ve been taking for years jumped in price.
Until January, I’d been paying $8.86 a month for the medication through my Humana Medicare Advantage plan. Suddenly, it jumped 200% to $26.85. In a series of calls, Humana agents gave me the following varied reasons:

The manufacturer increased the price.
I’d reached my donut limit for co-pays,

AROUND 2,800 YEARS ago, Homer’s Odysseus decided that the whole Trojan war enterprise, in which all of Greece would go to war and destroy an entire city because a woman ran off with a guy she liked, was crazy, so he tried to get out of going by pretending to be crazy himself. The Greek allies were suspicious that their cleverest leader was really crazy, so they sent an emissary to find out.
When the emissary arrived at Odysseus’s small city state,

FOR MOST SENIORS, purchasing Medicare Part D prescription drug insurance is the right move—even if they don’t require any expensive medicines right now. The coverage insures against the risk of someday needing prescription medication that costs thousands of dollars and might be otherwise unaffordable.

The federal government subsidizes Part D, so it’s cheaper than purchasing stand-alone private drug insurance. Another good reason to enroll in Part D at the first opportunity: You avoid the penalty associated with a late sign-up.

WHEN WE’RE YOUNG, we simplistically view our family’s money journey as one long road with clear signs that tell us to “speed up,” “change lanes” or “get off.” It’s only later, as we gain wisdom, that we can discern how messy the journey is—and how each of us ended up turning onto a different street to pursue financial freedom in our own unique way.
By exploring the money stories of three family members, I have come to better understand my own financial journey.

AS A FIRST-YEAR dental school student in 1999, when I was debating whether to apply for a military health-professions scholarship, I never gave a thought to receiving a military pension. In fact, I don’t even recall knowing that was a possibility.
I was already in debt to the tune of $65,000 from my undergraduate degree, so I was simply seeking financial aid for dental school, typically considered the most costly type of graduate education a person can buy—more so even than medical and law school.

I GOT OUT OF THE ARMY in August 1969. In the months prior, my wife and I discussed our financial plans. Simply put, if I was given a raise to $160 a week when I returned to work, we could buy some furniture for our small apartment. Bingo—we made it. I was earning $8,300 a year.

The other part of our plan was to save my wife’s salary toward a house down payment. She left the job market for good the following July,

HOME DEPOT COFOUNDER Bernie Marcus made headlines late last year with his claim that capitalism may not survive because “nobody works, nobody gives a damn.” I respectfully disagree. While Marcus has one example—people not wanting to work or work hard enough at the stores he founded—I believe America has a terrific future based on four observations:

I was a Boy Scouts leader for 16 years. I like to think that Scouts teach leadership and independence.

“I’D BE HAPPY TO JUST come here every year,” I told my husband. We and our two daughters had arrived on Maui 72 hours earlier. It was May 2000—and our first trip to Hawaii.
We’d signed up for a timeshare presentation in return for discounts on tours and activities. By the time we got to the meeting, I’d fallen head over heels in love with the place. The timeshare salesperson had an easy time persuading me to buy.