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,

AS I PULLED UP IN my used Subaru wagon to the high school drop-off line with two grumpy teenagers on the first day of school, I noticed something was different.
Because of the pandemic, our sleepy, semi-rural town in upstate New York had seen an influx of Manhattanites and Brooklyners over the past year. My Subaru was now bracketed by a shiny Tesla sedan and a polished Mercedes SUV. The usual collection of less flashy cars and trucks seemed to be missing.

ROUGHLY A QUARTER of my investment portfolio sits in three Roth retirement accounts. Ever since I first funded a Roth a dozen years ago, I’ve thought of this as money I’d avoid spending for as long as possible, so I milk maximum gain from the tax-free growth. But lately, it’s dawned on me that it’s highly unlikely I’ll ever dip into these accounts—and that realization has triggered a slew of investment decisions.
My three Roth accounts are all at Vanguard Group.

NOT ALL DEBT IS created equal—and that’s especially true when it comes to student loans.
For the vast majority of debt, we can calculate the ongoing monthly payment if we know the interest rate, number of payment periods, current balance and if the payment is due at the beginning or end of the period. But for federal student loans, we may need to know one more variable: the borrower’s discretionary income.
With federal student loans,

I REALIZE MOST FOLKS don’t find personal finance as enthralling as I do, so I apologize in advance—this article’s topic is the least thrilling of all. It’s time to talk about life insurance.
I’ve been trying to come up with a good analogy for life insurance. The best I can think of: Life insurance is like the airbags in your car. No one ever gets excited about airbags. No one ever shows off the airbags in their new car.

THE SECURE ACT, which took effect Jan. 1, 2020, made inheriting an IRA even more complicated. Before 2020, beneficiaries typically had the option of taking distributions from an inherited IRA over their lifetime, potentially squeezing many more years of tax-favored growth from these accounts.
The SECURE Act drew a new line, eliminating some beneficiaries’ ability to make use of the so-called stretch IRA. Beneficiaries now are divided into two groups. Some have to empty an inherited IRA within 10 years of the original owner’s death.

DESPITE WHAT’S SHOWN on TV medical shows, cardiopulmonary resuscitation (CPR) can be a traumatic procedure that has a low likelihood of success. Even if successful in immediately restarting the heart, the fact that it was necessary doesn’t bode well for long-term survival.
Some injuries or illnesses happen so suddenly that there’s little time to consider options. But for many, old age creeps up slowly or a serious illness drags on and worsens. This is the point where it’s helpful to have not just a living will and a health care power of attorney,

WHEN I STARTED flying for American Airlines in 1978, the industry was regulated. Routes, fares, airline size, pretty much everything the airlines did was controlled by the Civil Aeronautics Board. Then, later that year, the Airline Deregulation Act became law. Overnight, rules governing the industry changed.
This had far-reaching effects. But the biggest change was the cost of airline tickets. They became a lot cheaper.
Over the next 40 years, established carriers went bankrupt and disappeared.

MANY FOLKS SPEND December frantically hunting for ways to cut their taxes, whether it’s realizing losses in their taxable investment accounts, making charitable donations or raising their 401(k) contributions for the year’s final few paychecks.
A better strategy: Manage your taxes year-round rather than just at year-end. Filing a tax return is a reactive process—a record of income and deductions that have already occurred. It takes foresight and action to shape what those lines will look like on next year’s tax return.

THIS PAST YEAR marked my 50th anniversary of driving. Over that time, our family has owned 19 cars and driven them roughly 1.9 million miles. While latte purchases frequently evoke financial debate, cars seem less discussed, despite being Americans’ second-largest expenditure after housing. The purchase, ownership, maintenance and sale of cars can all get pretty complicated.
Cars are considered a depreciating asset, but not always. My first car was a 1967 Mercury Comet, which I bought for $400 in 1973.

WE OFTEN WRITE at HumbleDollar that saving and investing aren’t everything. Spending money on the right things—such as fulfilling experiences—can also be a great investment, especially if the dollars bring ample happiness.
Nearly seven years ago, I thought I’d wasted $4,000 on a foreign trip. But the law of unintended consequences has since worked in my favor.
The 2015 trip was supposed to be an investment in my career. I thought I could make a difference in the world and become a freelance foreign correspondent.

IF YOU FIND YOURSELF with a loved one in hospital who can’t make medical decisions, it can be overwhelming, intimidating and emotionally charged. Decisions are needed and each family member is conflicted: What would I want? What would the patient want? What do I want for the patient? The result can be sharp family disagreements.
Death, the prospect of death or even thinking about death is so loaded with emotion that it can hinder our willingness to prepare.

I WROTE PREVIOUSLY about my parents being victims of financial abuse by one of my brothers. Recently, I returned to Bangkok, which gave me a chance to discuss this situation at length with the entire family, including my other brothers and my uncle.

When the financial abuse of an elderly person is committed by a stranger, the rest of the family often has no chance to see warning signs. But 90% of abusers are family members or trusted individuals.

ECONOMICS IS ABOUT supply and demand. Call me biased, but I think why people demand particular goods and services is a whole more interesting than how suppliers do their thing.
It seems, however, that the topic of supply is unavoidable these days. We’re all hearing about supply chain woes. We’re all tired of seeing the empty shelf where our favorite crackers used to sit.
Even though economists will scream from the tallest Federal Reserve Bank building that supply and demand are separate and independent variables,

I GAVE THE BEST PEP talk I could muster, but it didn’t help. Our family of four entered Walmart in solidarity, planning to buy gifts to fill an Operation Christmas Child shoebox. Two of us left early in disarray.

I had to wrestle my screaming two-year-old all the way to the car because she knew only one way to approach the toy department—with herself in mind. Eliza melted down over her refusal to part with a cheap plastic toy.