The financial markets have two primary functions: to make us wealthy over time and drive us completely batty along the way.
NO. 75: WANT TO give to charity or family? We’ll boost happiness and possibly save on taxes by giving now. But if we’re struggling to fund retirement, we should bequeath the money instead.
NO. 108: OUR HUNTER-gatherer instincts tell us to consume right away—and not save for the future. What to do? We might automate our regular savings. We should visualize our goals, so they seem more alluring than today’s spending. We might share our financial ambitions with others, so fear of their disapproval prods us to spend less and save more.
NO. 7: WE'RE ALWAYS comparing ourselves to others. Thinking we’re in for a treat, we go to expensive resorts and renowned restaurants. Imagining it’ll make our life better, we move to a ritzy town where our neighbors are all wealthier. But instead of boosting our happiness, these actions can drag it down—because we’re reminded that others are better off.
CONFIRMATION BIAS. We like to imagine that we objectively assess information and reach unbiased conclusions. The reality: We often start with an opinion—and then latch onto information that confirms what we believe. Those bullish on stocks, for instance, will devour optimistic news reports, while ignoring those that are troubling.
NO. 75: WANT TO give to charity or family? We’ll boost happiness and possibly save on taxes by giving now. But if we’re struggling to fund retirement, we should bequeath the money instead.
WHEN A FRIEND TOLD me about his newfound interest in buying and selling sports trading cards, it reminded me of the joy that collecting brought me in my childhood. And when he asked me to explain the relevant taxation, it got me thinking: The core of the tax code is more logical than we give it credit for. It’s the ever-changing details that make it squirrelly.
If you buy and sell collectibles—whether it be sports cards,
WHEN I FIRST LOOKED at the issue of portfolio withdrawals more than two decades ago, many financial experts suggested retirees follow a simple strategy: spend taxable account money first, traditional retirement accounts next and Roth accounts last. That way, you’d squeeze more years of tax-deferred growth out of your traditional retirement accounts, and even more out of your tax-free Roth.
If only things were so simple today.
Why have portfolio withdrawals become more complicated?
GOT A VACATION home? There’s an overlooked tax break if you rent it out—but a potential tax hit if you sell.
First, the tax break: Long-standing rules allow homeowners to completely sidestep taxes on rental income—provided they meet a key requirement: They rent out their cottage or condo for less than 15 days during the year.
That can be a great tax break for those who own dwellings near annual events where rents soar for short periods.
I’M A DINOSAUR. Not only do I prepare my own tax return with no help from an accountant or tax preparer, but also I do it by hand. Yep, that’s right—no TurboTax or other computer program.
I really can’t use the computer programs because I often attach an oddball form or two that they don’t offer. On top of that, I always add “annotations” to parts of my return. These additional explanatory notes may be helpful to the IRS.
ONE OF MY FAVORITE things to do is sit on our local beach with a cold beverage on a beautiful day, and talk finance with interested friends and family members. This past Labor Day weekend, I did just that with a soon-to-be retiree.
One of the big issues facing him and his wife: where to live. He had been relocated to New York by his employer. But he and his wife are natives of the Philadelphia region,
ONE OF THE GREATEST business books I’ve ever read is Antifragile by Nassim Nicholas Taleb. In it, he postulates the idea that, while things that become damaged by stress are considered fragile and things that resist stress are considered resilient, “there is no word for the exact opposite of fragile,” things that become stronger due to stress. So, he coined the word “antifragile” and then wrote an entire book about the subject.
What words of wisdom would you have for your younger self?
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Thank you, Jonathan
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The C Word
Jonathan Clements | Jun 15, 2024
ON SUNDAY MORNING, May 19, I was enjoying croissants and coffee with Elaine at the kitchen table, while watching the neighborhood sparrows, finches, cardinals and squirrels have their way with the bird feeder. All was right in our little world, except I was a little wobbly when walking—the result, I suspected, of balance issues caused by an ear infection.
It was going to be a busy week, and I figured that it would be smart to get some antibiotics inside me, even if visiting the urgent care clinic on Sunday might be more expensive than contacting my primary care physician on Monday and perhaps having to go in for an appointment.
Long story short, I ended the day in the intensive care unit of a local hospital, where the staff discovered lung cancer that’s metastasized to my brain and a few other spots. This, as you might imagine, has meant a few changes in my life, and there will be more to come.
I have no desire for HumbleDollar to become HumbleDeathWatch. But my prognosis is not good. I've had three brain radiation treatments and I started chemotherapy yesterday, but these steps are merely deferring death and perhaps not for very long. I’ll spare you the gory medical details. But as best I can gather, I may have just a dozen okay months ahead of me.
Weirdly, as of right now, I feel pretty darn good, and perhaps better than most 61-year-olds. Every morning, I’m stretching and lifting for 20 minutes, and then riding a stationary bike for 40 minutes. And in case you’re curious, I was never much of a smoker and last had a cigarette in 1987, when I was age 24. Instead, it seems my lung cancer is the result of a defective gene—one that's rare and without a promising treatment plan.
In future articles, I’ll be writing more about the personal finance and other implications of my diagnosis, which I believe have an intriguing relevance even for those without an incurable disease. I also suspect readers want to know my plans for the site. The Reader’s Digest version: I intend to keep HumbleDollar going, though there'll be some notable changes. But before I get to those changes, here are some initial financial thoughts, which I hope to discuss further in the weeks and months ahead.
Managing money is fraught with uncertainty, but never more so than now. There’s much I don’t know—how long I’ll live, how long I’ll be able to do the work I love, what my medical and other costs will be. Still, on this score, I’m hardly alone. In varying degrees, we all face this sort of uncertainty, and it’s one reason managing money is so fascinating.
Money is intimately bound up with regret. We often berate ourselves for the foolish purchases and investments we make. This one has been a pleasant surprise: Until the past few years, I’ve lived quite frugally, and yet I find myself with almost no regrets about that lifestyle. Yes, if my health allows, I’ll be ticking off some bucket-list items over the year ahead. But mostly what I feel is profound gratitude for the life I’ve had. I’ve had amazing opportunities and wonderful experiences, and that allows me to face the time ahead with surprising equanimity.
The cliché is true: Something like this makes you truly appreciate life. Despite those bucket-list items, I find my greatest joy comes from small, inexpensive daily pleasures: that first cup of coffee, exercise, friends and family, a good meal, writing and editing, smiles from strangers, the sunshine on my face. If we can keep life’s less admirable emotions at bay, the world is a wonderful place.
We can control risk, but we can’t eliminate it. I’ve spent decades managing both financial risk and potential threats to my health. But despite such precautions, sometimes we get blindsided. There have been few cancer occurrences in my family, and it’s never been something I had reason to fear. Chance is a cruel mistress.
It’s toughest on those left behind. I’ll be gone, but Elaine and my family will remain, and they’ll have to navigate the world without me. I so want them to be okay, financially and emotionally, and that’s driving many of the steps I’m now taking.
Generosity suddenly feels so much sweeter. No doubt part of the reason is that I’ll no longer need most of my retirement savings, plus there’s scant reason to acquire new possessions. Perhaps part of me is also more anxious to earn the good opinion of others, while I still have the chance.
But there’s another aspect to this: As I watch friends and family react to my diagnosis, it makes me appreciate that most folks have an inherent goodness and they’re constantly struggling to do the right thing, and a little generosity is a way to acknowledge that.
Life’s priorities become crystal clear. Even at this late stage, I believe it’s important to have a sense of purpose, both professionally and personally. I can’t do much about the fewer years, and I have no anger about their loss. But I do want the time ahead to be happy, productive and meaningful.
I’ve been moving to further simplify my finances, organize my affairs and make things right with those around me. Underlying this is a desire to control what I can—hardly surprising, given the uncertainty swirling around me—and I’m probably overdoing it.
There’s one aspect of my life over which I have a fair amount of control: HumbleDollar, this little world I created and that all of you, with your comments, articles and support, have helped build. That brings me to my plan for the site. Even before my diagnosis, I had been noodling how to scale back the site in 2025, with a view to having a little more time for travel and such.
I’ve accelerated those plans. Starting next month, my goal is to run four or five new articles each week, rather than the dozen or so that the site publishes today. But that’ll partly hinge on how I react to treatment and how quickly my health deteriorates. Meanwhile, next week, I hope to unveil a new feature that'll allow the site's writers and readers to continue to interact with one another.
One change I’ve already made: I’ve removed the site’s donation feature and cancelled all recurring donations. Many thanks to those of you who have supported HumbleDollar financially over the years. With the site posting fewer articles, I didn’t feel it was right to continue accepting donations.
Farewell Friends
Jonathan Clements | Sep 22, 2025
Throw, hit or kick … it all add$ up
R Quinn | Sep 27, 2025