WHEN I ANNOUNCED I’d be retiring at age 55, the most frequent question I received from friends was about how I’d pay for health insurance. They knew I wouldn’t be eligible to receive Medicare for a decade. They also knew paying for 10 years of premiums would likely leave a large crack in my nest egg.
Fortunately, I was able to take advantage of a health insurance benefit provided by my former employer. As an early retiree,

I’M BASICALLY A BORING kind of guy. I’ve been known to fall asleep during a raging house party. But when it comes to travel, you’ll find me wide awake. It’s one of my favorite things to do.

Given the hassle of international travel right now, Connie and I decided to see more of the U.S., rambling from state to state, planning no more than a day or so in advance.

We’ve just finished our third cross-country road trip since 2014.

AS ANYONE WHO HAS spent time around kids can attest, emotions often run high when things don’t go according to plan. Recently, my three-year-old daughter, Carter Rose, refused to brush her teeth, wear clothes or go to school.
Rather than going head-to-head with an emotional toddler, I took the approach of listening, compassion and empathy to get things back on track. What was wrong—and what could make things better?
We could all use a little more empathy these days.

PERSONAL FINANCE gurus and bloggers will tell you that lifestyle creep—the tendency for spending to rise along with income—is one of the greatest barriers to building wealth. While that’s sometimes true, I believe it can also be a source of joy and reward.
After all, while we might work hard to get a pay raise or earn a big year-end bonus, what a lot of people are really striving for is the ability to increase their spending.

AS WE CELEBRATE Thanksgiving, I’m reflecting on what I’ve learned over the past year or so from HumbleDollar—both as a reader and as one of the site’s writers.
An article I wrote about claiming Social Security bounced back and forth a few times between me and HumbleDollar’s editor, Jonathan Clements. The breakthrough came when Jonathan referred me to a free online calculator built by financial blogger Mike Piper. I’d been trying to do my own calculation in Excel.

I’VE BEEN AWAY FROM the HumbleDollar community for a while. Jiab and I are working on a new book about media literacy, examining the effects of social media influencers on youth consumerism. It will teach kids about responsible web use and how to avoid the traps of the online world.
I’ve learned a lot myself, including lessons that apply both online and IRL, short for “in real life.” As part of our research,

I’M GOING TO SHOW you how to lose money. All you need to do is avoid some simple math, while embracing the widespread but illogical fear of health care costs.

Years ago, I designed employer health plans that gave employees several choices. Each option covered the same health care services. The differences among the options were the deductible, out-of-pocket maximum and premiums. The lower the deductible, the higher the premium you paid. Over time,

LIKE MANY RETIREES, I’ve thought about moving. My two children are living elsewhere, and I have no other family in the Florida city where I’ve resided for more than 17 years. For two years, I’ve researched buying a condo closer to the ocean or even moving to Mexico, where my modest fixed income would go much further. Perhaps I should return to my hometown up north—something two friends from high school have already done.

YOU KNOW IT’S BEEN a rotten year for investors when it’s time to brush up on the rules for tax-loss harvesting. It’s one way to turn negative returns to your advantage, provided you act before year-end.
If you have taxable investments that have lost value this year—and who doesn’t? —the basic idea is to sell them in 2022 to lower the taxes you owe. Realized losses can be used to offset any investment gains you’ve realized this year.

THE FTX FALLOUT IS something to behold. It’s said that the now-bankrupt cryptocurrency exchange has liabilities that could end up being twice what Enron owed when it collapsed more than two decades ago. The hubris of Sam Bankman-Fried (also known as SBF), founder of FTX, is something all investors can learn from.
It was just a few months ago that Bankman-Fried was dubbed the next Warren Buffett and 2022’s version of the late 19th and early 20th century financier J.P.

A UNIVERSAL TRUTH about market bubbles is that they’re​ masters of disguise. Each new bubble appears different enough, at least on the surface, to reel in unsuspecting investors. While bubbles are almost as old as the market itself, the latest example—centered around the cryptocurrency exchange FTX—is particularly impressive. At this point, no one is 100% sure what happened, but this is what we know so far.
Back in 2017, a 25-year-old MIT graduate named Sam Bankman-Fried started a hedge fund to trade cryptocurrencies.

WHEN I PICK HEALTH insurance each year, my focus is twofold: What’s the monthly premium—and what’s the out-of-pocket maximum?
Sure, I want to stay with my primary care physician. But my doctor just announced that she’s leaving Philadelphia to return to her native Massachusetts, so that became a non-issue for 2023.
Meanwhile, I’ve long wanted a high-deductible health plan so I could fund a health savings account (HSA). But since 2014, when I started working for myself and had to buy individual coverage,

PESSIMISTS SEEM LIKE they’re clever and sophisticated, but—if you want to make money—take my advice: Invest like an optimist.
I’m not talking wild-eyed optimists who are over-enthused about meme stocks and nonfungible tokens. Instead, I’m talking about a fundamental belief that economic setbacks are temporary and the future will be better than the past. Struggling to stay cheery amid 2022’s rotten financial markets? Here are five reasons for optimism.
1. The news is terrible.

WHY DO SOME PEOPLE save more for retirement than others, even when their income is the same? It turns out that a difference in spending behavior, rather than a larger salary, may separate better savers from those who struggle to set aside funds for their future.
The Employee Benefit Research Institute and J.P. Morgan Asset Management joined forces to examine the spending and saving behavior of 10,000 households. The households, which were analyzed by age cohort,

I LOOKED UP OUR investment account balance recently. It’s something I’d avoided doing for months. My wife, the voice of reason, said we might bounce a check if we didn’t know how much was in the money market fund. Confession: I don’t balance our checkbook manually.
I waited to log on until after the Dow Jones Industrial Average shot up 14% in October, its best month since 1976. I don’t know why the bear lost its grip on the Dow last month,