I QUIT MY JOB last year and then found I needed medical care. My old employer was required to offer me health insurance—but it was expensive. Luckily, I found a loophole that allowed me to obtain the coverage I wanted at a bargain price. I got the treatment I needed, and saved almost $1,000.

First, a bit of background. More than half of the U.S. adult population gets health insurance through their employer. Indeed,

I HATE TO BE WRONG. I’ve written before about the technique I’ve developed for evaluating health insurance. My wife and I have used it over the years to decide which plan to select. I’ve shared it with friends and colleagues, and many have found it useful in gaining insight into their own health insurance options. I still think it’s a valid and valuable method.
But our recent experience, after switching health insurance mid-year, made me realize it was missing one important variable—the length of time you’ll be in the plan.

IS A DEGREE FROM AN elite school the golden ticket? I recently read Jeffrey Selingo’s excellent book Who Gets In and Why—and came away with some fascinating insights.
Selingo says experience and skills often trump where someone went to college. Each year, 1.8 million students graduate from four-year colleges, with 54,000 leaving with a degree from an elite institution. Simple math confirms employers must fill jobs with more than just graduates from elite schools.

GOT CHARITABLE giving on your mind? Join the crowd. Many folks donate at this time of year, with their charitable giving driven by the charities themselves.

As solicitations arrive, people decide on a case-by-case basis whether to pull out their checkbooks. But some folks follow a more structured process, and that’s the approach I favor. It includes asking these three questions:

1. How much ideally would you like to give? As a starting point,

IF YOU’RE LIKE ME, you almost dread looking at the morning newsfeed. This is why I’m happy to share some good news: The U.S. poverty rate has been cut nearly in half. What’s more, it was accomplished while the economy was practically flat on its back, with tens of millions out of work.
When I was a Washington, D.C., reporter in the mid-1990s, I reported from some of the poorest neighborhoods in Baltimore, Camden and Washington.

MY MOST MEMORABLE experiences are family vacations—and that includes the mishaps. Those become the stories we laugh about years later.
For instance, when our boys were young, we took an overnight train from Bangkok to northern Thailand. We found ourselves trapped for three days in Chiangmai by an unexpected torrential flood. Multiple times, we had to modify our plans for getting back to Bangkok. Finally, we got a flight on a small airplane. As we walked up to the plane,

RON LIEBER, in his book The Opposite of Spoiled, describes a 2012 conversation between Chris Rock and Jon Stewart. In an interview on Stewart’s show, they got around to discussing the challenges both faced in raising children who could remain grounded amid wealthy surroundings.

Rock described how his own modest upbringing differed from the comfortable life his children enjoy. “My kids are rich,” he said. “I have nothing in common with them.”

Stewart agreed.

MILLIONS OF RETIRED baby boomers struggle financially, and yet they don’t eat avocado toast, don’t have a daily Starbucks habit and didn’t graduate college with a degree in women’s studies.
What’s my point? In the comments section of HumbleDollar, there are two recurring themes—that young adults spend recklessly and that college is of questionable value. I understand these concerns and even share them to some extent. But I’d favor a more nuanced view.

JIM AND I JUST CAME back from two weeks’ vacation in Greece and Turkey. We planned the trip at the last minute, and booked our tickets less than a week before flying.

 Many imagine high prices when they think of travelling abroad. But in fact, there are many international destinations that are more affordable than vacationing in the U.S. We spent much less on lodging and food—the costliest items after airfare—than we would in America.

WHAT’S THE REAL PRICE? In September, I wrote about the potential tab for sending our first child to college in 2025. The four-year cost was estimated at anywhere from $65,000 to $430,000, depending on the college chosen.
This wild disparity led me to conclude that college financial planning was like saving to buy a car—when you don’t know if you’ll drive off the lot in a Honda or a Lamborghini.
Since then, I’ve tried to put a sharper pencil to college costs.

AS A MEMBER OF THE lucky sperm club, I reluctantly joined my father in business in 1970. I know it was his dream, but it wasn’t mine. He started his cash register business in 1938 and, by the time I signed on, the industry was still steep in mechanical devices. Not my passion. I liked electronics.
Still, I agreed to do things his way and learn the business from the ground up. He said the first thing I had to do was learn to sell.

LIFE IS EXPENSIVE—especially for young adults contending with budget busters like housing and tuition. If you have adult children facing these expenses and want to help them financially, you may be wondering what’s the best approach. While every family is different, below are three principles that I’ve seen work well.

1. Transparency. This applies in several ways. First, you should let your children know your objectives for these gifts. Do you want to see them spend it on something specific—such as a home down payment—or are they free to use it as they see fit?

SIX YEARS AGO, a colleague came into my office, looking concerned. He asked if I could speak with a client who was suffering from dementia. At the time, I was the Army’s attorney in charge of legal assistance at Fort Hood, Texas. One of the services we provided was drafting wills for servicemembers, veterans and their families.
For our legal office, my policy was that I’d always be the person to deliver bad news.

MY BROTHER-IN-LAW just told me about a technology issue that he’s been struggling with. He was trying to get an old scanner to connect with his Mac. The solution required him to upload some outdated software.
When he finished explaining how he resolved the issue, I was happy he could scan again. I was even happier that I had a $250 personal computer. Nothing irks me more than paying a premium—the Mac premium, in his case—and winding up with connectivity issues.

IT’S OPEN SEASON for many of us—time to choose our health insurance for the year ahead. It’s a topic I got seriously interested in when I took over management of 500 mathematically astute engineers. They challenged me daily to understand how the various plans stacked up against each other. I spent a lot of time looking at various ways to assess the value of the different plan choices, and came up with a framework that worked for my family.