AS FOLKS HURTLE toward retirement, they often wonder whether they’ve saved enough, debate when to claim Social Security and fret about how they’d pay for long-term care. Make no mistake: Such issues are hugely important.
But amid these financial musings, we should also spare a thought for four other questions:
How can I transform myself from a diligent saver to a happy spender? This sounds so easy, and yet many struggle with it,

WHEN I WAS ASSIGNED a high school essay on business morals, I asked my dad if he knew of any books on the topic.
“No, Stevie, I don’t. From what I’ve seen in New York real estate, it would be a very thin book.”
For more than 40 years, that cynical quip has haunted me, coloring my view of rental real estate. I’m not emotionally suited to being a landlord. But I wanted real estate as a stock market diversifier—and I was drawn to the benefits of combining rental income with stock market dividends.

IN MY LAST ARTICLE, I wrote about how Harvard and other colleges are offering programs to help growth-oriented retirees find new meaning and purpose. Having a sense of purpose improves our quality of life and provides a sense of well-being.
But most of us, including this writer, can’t afford Harvard’s program. That’s why I’m going to show you how to find your main reason for being within the comfort of your own home—using the ikigai method.

FINANCIAL FRAUD against Americans age 60 and older costs $3 billion a year, and the average loss per incident is $120,000, according to a 2020 study by the AARP Public Policy Institute. And scams against older Americans are increasing. The FBI reports that losses more than doubled from 2019 to 2021 and internet swindles against elderly victims rose 84% in 2022.
My wife was the target of a fraud and you may have been,

I RECENTLY LISTENED to an interesting Hidden Brain podcast discussing different ways of bringing about behavior change. The guest on the podcast was Loran Nordgren, a professor at Northwestern’s Kellogg School of Management and coauthor of a book entitled The Human Element. The discussion centered on two related concepts: fuel and friction.
Fuel is the stuff we use to motivate ourselves and the people in our lives. It can be positive or negative.

IF MEDICARE’S A MAZE, its Part D drug plan is a maze within a maze, with no one good path and plenty of so-so choices, along with a couple of potential “gotchas.”

Until 2006, Medicare offered no coverage for outpatient drugs, so today’s situation—however imperfect—is certainly an improvement. It’ll improve even more for people with high drug costs in 2024 and 2025, as I’ll explain at the end of this article.

What if you have Medicare Advantage,

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,