AS I NOTED LAST WEEK, investing can be maddening. But it isn’t just investing. Many other personal-finance questions can also drive us crazy. Why is that?

One reason: The stakes are often high, so mistakes can be costly. A second reason: By definition, all data are historical, but all decisions are about the future. To the extent that the future doesn’t look like the past, we have a problem.

Those two factors are very real.

IT’S OFTEN SAID THAT beauty is in the eye of the beholder. The same could be said of fairness in taxation.
A recent article by Kelly Phillips Erb addresses this contentious topic. Erb, who tweets as @TaxGirl, is the team lead for insights and commentary at Bloomberg Tax and Accounting. Her article was titled, “Did you pay your ‘fair share’ of federal income tax this year?”
The piece discusses the history and current state of U.S.

IF YOU GOOGLE “best business books of all time,” you’ll find Napoleon Hill’s Think and Grow Rich at or near the top of the search results, ahead of works by luminaries such as Ben Graham and Jack Bogle.
Truly helpful business analysis requires the reader to pay attention to evidence backed by boring data, a formula that’s hard to sell to the masses. Books like Think and Grow Rich or Jim Collins’s Good to Great offer the reader questionable assumptions built on anecdotal evidence,

EVERY LEGITIMATE short list of history’s greatest basketball coaches includes Pat Summitt and John Wooden. I’m not even going to attempt to recount their myriad successes. Instead, I want to discuss why they were successful.

Many of the best to ever play basketball went to the University of Tennessee and to the University of California, Los Angeles, to work with these legendary coaches. When players like Candace Parker and Kareem Abdul-Jabbar (then Lew Alcindor) stepped onto the floor,

THE RECENT CARNAGE in bonds has been unusually fierce. The Bloomberg Aggregate Bond Index is down more than 7% year-to-date. Unfortunately, this may be the tip of a very large iceberg. I believe we may be standing on the precipice of a multi-decade bear market for bonds.
The reason for my concern can be summed up in one word: inflation. It’s the great enemy of bond investors—and yet, despite an inflation rate that’s at four-decade highs,

MY WIFE DECIDED TO sell the house she bought before we were married. We’re both retired and I view it as another step in our ongoing efforts to simplify our financial lives as we age.
My wife and I interviewed a real estate agent who was recommended by a friend. Steven suggested we do some minor repairs before listing the house. Steven also gave us his opinion on the sale price. He told my wife she had a nice little starter home and we should list it in the middle of the estimated price range.

AT THE BEGINNING of 2022, I wrote about our resolution to go back to grad school. The short update: Jiab and I are indeed doing it. We’re enrolled in the Master of Arts in Interdisciplinary Studies program at the University of Texas at Dallas.
We scrambled to get the application paperwork done before classes started Jan. 18. Neither of us had applied to school for ourselves since the introduction of online registration, but we found it fairly easy.

WHEN PLANNING OUR early retirement, I realized that getting and paying for health insurance for my wife and me would be our biggest financial challenge.
Before 2010’s Affordable Care Act (ACA) took effect in 2014, we talked to an insurance agent who gathered our medical histories and submitted them to insurers for consideration. Despite two major surgeries, I was deemed insurable. My wife, due to a congenital condition that had never caused a problem but might,

THE SIREN SONG of a side hustle is alluring in theory—but not in reality. We’re beset by platitudes such as “to become wealthy, you need multiple streams of income.” Many folks, I suspect, take on a side hustle without fully understanding the costs. They imagine it’s an opportunity to monetize their hobbies or interests and achieve their financial goals faster.
Let’s face it: “Second job” just doesn’t sound sexy, so financial bloggers and the media favor “side hustle,” an apparently more glamorous term.

I JUST LEARNED a hard lesson about insurance companies: They have the upper hand.
Water leaked into my ground-floor condo’s bathroom and laundry room from a unit two floors above. The unit owner offered to report the damage to his insurance company, but I decided I should call mine for advice. A rep told me that I could file claims with my insurer and it would then seek compensation from the other unit’s insurance through subrogation,

JERRY SEINFELD tells a story about visiting the post office and noticing a wanted poster on the wall. He looks at the poster and checks the guy standing behind him. “If it’s not him,” he says, “I feel I’ve done my part.”
I own some individual stocks, so it’s that time of the year when I vote my proxies. I do the best I can at trying to understand the issues. Sometimes, I wonder whether I’ve really accomplished anything.

NEW HAMPSHIRE’S STATE motto is “live free or die.” But for my wife and me, the first part might be better expressed as “live tax-free.”
We just moved to New Hampshire from Maryland. The move’s main purpose is to be near our kids, enjoy lake and mountain activities, and experience cooler summers. But New Hampshire’s zero tax rate on earned income, pensions and capital gains is a major bonus.
Eight states have no tax on personal income,

INVESTORS ENDURED a lot in the first quarter, including rising interest rates, high inflation, fears about a recession and news of war. But it’s important not to get caught up in the scary headlines. Consider COVID-19. Not so long ago, it dominated the news, but now it’s hardly discussed because the situation is much improved.
No doubt today’s fears will also abate. Indeed, despite 2022’s dire news, stocks staged an impressive recovery toward the end of the first quarter.

INVESTING CAN BE maddening. Stocks that look like they’re going up can end up falling, while investments that look like they’re headed for the dustbin can suddenly bounce back. This leaves investors in a difficult position—because the right thing to do often feels wrong.
Investing requires us, quite often, to act contrary to our own intuition. Here are four examples.
1. Don’t equate price with quality. When consumers walk into a retail store,

MY BROTHER AND I recently reminisced about the investment club we helped found in the late 1980s. The club’s benefits were threefold: financial education, the pooling of money and camaraderie.
Our club was composed of family and friends. We met monthly. When we started, investing was largely a manual process. There were few discount brokers and even they charged relatively high fees. You bought and sold with a phone call, and mailed checks for payment.