JONATHAN CLEMENTS’S final book was released this week. Titled Money and Me, it traces the arc of Jonathan’s nearly four-decade career as a personal finance columnist.

Money and Me starts with the story of a man named George Cope, who was a nineteenth century tobacco baron. At the time of his death in 1888, Cope was one of Britain’s richest men. But within just two generations, his fortune was gone. Why? Cope’s daughter was the sole heir to her father’s fortune, but she lived what Jonathan described as a Downton Abbey lifestyle, on an estate in the Cotswolds with five homes and eight children. Before long, the fortune was gone.

This story was of interest to Jonathan because George Cope was his great-great-grandfather. He called it the “big family story” and explains that this hard financial lesson was imprinted on everyone in his family from a young age.

In part because of this family story, Jonathan got interested in personal finance, and, among his peers, was early in focusing on the psychology of money. “I like to think I’m rational in the way I spend my dollars, and I suspect most readers do, too. We are, of course, deluding ourselves,” he wrote.

Early in his career, Jonathan covered mutual funds for Forbes, then The Wall Street Journal. Each week, he'd review a different fund and interview the fund’s manager. From that vantage point, he was early in recognizing a reality about Wall Street: that they’re great marketers but not such great investment managers. After reviewing scores of actively-managed funds, Jonathan came to the conclusion that index funds were a better way to go for most investors.

Since the investing question was “solved,” as he put it, by index funds, Jonathan turned his attention to other domains in personal finance. The relationship between money and happiness was of particular interest. Though he acknowledged that each of us has a happiness “set point” that is largely fixed, he pointed out that our happiness level isn’t entirely fixed. There’s plenty we can do to move the needle.

A chapter titled “15 Ways to Happy” includes a number of practical suggestions. Among them: Jonathan always recommended making plans—especially vacation plans—far in advance. Why? “Often, the best part of a purchase or experience is the anticipation,” he explained.And since it doesn’t cost more to book early—indeed, it often costs less—that was his recommendation.

Jonathan leaned heavily on academic research and helped translate its findings for everyday investors. In Money and Me, he explains concepts from psychology including the hedonic treadmill, eudaimonic happiness and many others. Jonathan acknowledged that there’s no magic wand for achieving happiness. On the other hand, he explains why a million-dollar salary isn’t a necessary ingredient for financial contentment.

Jonathan also wrote a lot about spending. On the one hand, owing to his family’s experience, he developed frugal habits early in life, and he was grateful that those habits led to financial independence by age 50. On the other hand, he knew that frugality could be taken too far. In a chapter titled “Don’t Overdo It,” Jonathan offers a menu of ideas to help others who might similarly struggleto loosen the purse strings.

Jonathan had two children and thought a lot about how best to convey money values to them. He knew the risk in helping too much. “Money doesn’t necessarily kill all ambition. But it seems to put a big dent in financial ambition,” he wrote. For that reason, Jonathan mostly emphasized education rather than direct financial assistance. 

He describes, however, one important way in which his own parents helped him: They always made it clear that they were there for him as a backstop. Though he might have never needed it, simply knowing this support was in the background gave Jonathan the confidence to always invest heavily in the stock market. He describes maintaining an allocation to stocks that was regularly above 80% or even 90%. That kind of aggressive investing ran contrary to the textbook. But recognizing the benefit it had provided during strong markets over the years, Jonathan offered a similar backstop to his own children, thus allowing them to take risks that they might not have otherwise.

In choosing a heavy allocation to stocks, Jonathan explains some of the other factors that went into his thinking. For starters, he points to the role of financial forecasters. They’re often wrong, but that doesn’t stop them from waking up the next day with something new to say. As a result, during both stock market rallies and routs, prognosticators can be found on TV telling stories that often cause investors to overreact. In the chapter “Not Scared of Bears,” Jonathan walks through the math that should give investors the courage to ignore forecasters, to keep their feet on the ground and to stay fully invested regardless of what bad news happens to be in the headlines.

Jonathan was willing to pile on even more risk in his portfolio when markets declined. He acknowledged that this opened him up to the accusation of being a market timer—“pretty much the nastiest insult you can hurl”—but he explains a subtle difference between his approach and true market timing, then offers a helpful strategy for profiting from downturns.

Jonathan Clements was one of a kind. Like all of his readers, I miss his kindness, wit and good cheer. For decades, he helped readers navigate the potholed road known as Wall Street. With his final work, Jonathan leaves us with a timeless guide to thinking about money in uniquely sensible ways.

WHEN I STARTED writing for HumbleDollar, Jonathan gave me some simple but important advice: “Don’t brag about your financial situation. You want readers to like you.” Perhaps that’s one of the reasons he named his financial site HumbleDollar.

I try to follow this advice not only regarding money, but in other aspects of my life. I know how fleeting things can be—especially when it comes to health. Life can change on a dime. It can humble you.

At age 75, I’ve been fortunate with my health. I have had no major illnesses or pain that slowed me down. I could do pretty much whatever I wanted to do. However, that suddenly changed.

About a month ago, I experienced pain in my right eye, a mild headache, and nausea. I thought it might be the flu until I started seeing double.

I went to my optometrist, who said I should see a neuro-ophthalmologist. Because I have Original Medicare, I was able to see one the next day without waiting for a referral. Both physicians were paid for by Medicare and my supplemental insurance because it was a medical issue.

Without getting too far into the weeds, it was determined that one of the three cranial nerves controlling my eye movements was weakened because of temporary poor blood flow. Folks who have diabetes, high blood pressure, high cholesterol, or who are older face a higher risk of developing Microvascular Cranial Nerve Palsy.

The good news is that, in most cases, the nerve is not permanently injured and recovery occurs over six to 12 weeks. The double vision can be treated in the short term by patching either eye or attaching a temporary prism to your eyeglasses. The temporary prism is no longer working for me, so I have to use a patch.

It has been four weeks and, no pun intended, it has been a real eye-opener. I can’t drive and must rely on my wife to take me places. I’m beginning to get a taste of what it is like to lose my mobility.

I’m usually the one who does most of the shopping, so this has added more tasks to Rachel’s to-do list. We now use Amazon Prime more often to have items delivered to our house. One of my greatest fears is that I might become a burden.

When we’re out, Rachel wants to hold my hand because she’s afraid I might fall. Although I appreciate the help, it makes me feel older and weaker. I haven’t told any friends or family about my condition. I guess I have too much pride—or shame—to admit that I need help taking care of myself.

Don’t get me wrong, I’m lucky to have someone helping me through this ordeal. I have also learned something about myself.

What surprised me most is how much of my identity was wrapped up in being independent. I spent the first 10 years of my retirement taking care of my parents. I liked being the helper, not the one needing help. I liked driving, shopping, carrying things, fixing problems, and taking care of myself. Losing some of that, even temporarily, has been harder emotionally than physically.

Maybe that’s why setbacks like this humble us. They remind us that none of us is fully self-sufficient, no matter how healthy, capable, or financially secure we may feel. At some point, we all depend on others.

Rachel hasn’t complained once. She simply adjusted. She drives me where I need to go, walks a little closer beside me, and is always there to lend a helping hand. What I first saw as weakness on my part, I’m beginning to see differently. Allowing someone to help you can also be an act of trust and love.

This experience has also made me think about the future. Many of us spend years planning financially for retirement, but we don’t spend nearly as much time preparing emotionally for the possibility that someday we may need help ourselves. That may be one of retirement’s hardest lessons.

I also understand why most elderly people want to age in place. Perhaps like me, they find the emotional challenge of giving up some independence hard to fathom. But I'm beginning to realize that Rachel and I are going to need help in our later years. It comes down to what kind of help we are looking for.

We don’t just need a financial plan for when our health changes; we need a care plan. For Rachel and me, aging in place will mean redefining what help looks like. It might mean:

Most importantly, it means having difficult conversations now about what we will do if a temporary setback becomes a permanent reality. For instance, how much of our portfolio are we willing to allocate to home-health aides before considering an assisted living facility? What physical benchmarks signal that it’s time to hand over the financial reins to a trusted executor?

We spent our lives living below our means so we could build financial safety nets and not have to depend on anyone. But as it turns out, the most valuable asset we have in retirement isn't our robust portfolio. It’s the person holding our hand when the world goes blurry.

Fortunately, my condition will likely improve with time. I’m grateful for that. But even this temporary detour has given me a deeper appreciation for good health, Medicare, my wife’s support, and the everyday abilities I once took for granted.

Life has a way of humbling all of us eventually. Maybe the best we can do is accept it with a little grace—and remember that someday, almost everyone gets a turn being the one who needs a hand.

Dennis Friedman retired from Boeing Satellite Systems after a 30-year career in manufacturing. Born in Ohio, Dennis is a California transplant with a bachelor’s degree in history and an MBA. A self-described “humble investor,” he likes reading historical novels and about personal finance. Follow Dennis on X @DMFrie and check out his earlier articles