I RECENTLY STARTED reading Think Again, the new book by Adam Grant. Subtitled The Power of Knowing What You Don’t Know, Grant’s book got me thinking about all the ways that, over the years, conversations with clients have led me to look at things through different lenses. Below are eight such topics:

1. There’s one important financial question that stumps most everyone—for good reason. In building a financial plan,

ONE OF THE TOUGHEST financial challenges most people face—second only to accumulating enough for retirement—is deciding how to convert those funds into retirement income. Especially when the goal is to never run out of money.

I pride myself on being informed. This morning, I received my comeuppance. I was reviewing my 401(k) account, which is administered by Fidelity Investments. I had taken my required minimum distribution for 2021, but was exploring other ways I could withdraw money.

I’M A MORNINGSTAR subscriber. I find that the site provides investing and personal finance information that’s sensible and useful for the average person, and that it promotes good investing and planning behaviors. Still, I was taken aback by a recent article, which discussed four funds that investors have been buying.
In terms of deciding what I buy, I don’t really care what others have been purchasing. Still, it’s interesting to see, so I checked it out.

HAVING LEFT the nine-to-five world, I face a decision: What to do about health insurance? I’m a single, generally healthy millennial. Historically, I’ve not run up major medical bills. But as with the financial markets, past performance doesn’t guarantee future outcomes. Here are the five options I’ve been considering:
1. Continue COBRA. When I left my job, I kept my old employer’s health plan, but I have to pay the full cost of coverage.

IT’S EMBARRASSING to admit in a public forum that I failed at retirement. But I’m doing so—because I think people can learn from me, and thereby avoid making the same mistakes.
I spent my entire 38-year career in the banking industry. Naturally, I learned a lot about money and investing. I helped thousands of clients save for their own retirement. On top of that, my wife is an investment advisor.
But despite all that knowledge and expertise—and having enough money to retire comfortably—I still managed to find my way into retirement hell.

AMONG PENSION PLANS, foundations and other institutional investors, the dream is to invest with top-quartile money managers. But, alas, that appears to be an impossible dream. Most managers end up disappointing.
Sadly, it’s the same for everyday investors who buy actively managed funds. Most funds wind up lagging behind the market averages, and that’s before factoring in the high taxes these funds often generate and the extra risks they take.
Lots of reasons for this failure have been identified: Money managers stray from their investment discipline,

AND SO IT BEGINS again—trying to figure out the mess that is Medicare.
A 132-page book from the Department of Health & Human Services arrived in the mail recently. “Medicare & You 2022” is four pages longer than the 2021 edition I received earlier this year, when I was turning age 65. I could barely bring myself to pore through the pages of that one, as I endeavored to understand the myriad choices facing me as I hit that magic milestone.

I WAS SITTING AT MY computer one lunchtime when an email popped up from one of my credit card companies, saying I’d just purchased nearly $12,000 of jewelry at a store in Toronto. Within minutes, I was on the phone to the card company.
I was quickly referred to the fraud unit. I told my story. The company credited my account, cancelled the card and mailed me replacements. Weeks later, I had to complete a form,

TIME AND AGAIN, we’re reminded to fully understand a question—particularly when the question is complex—before acting or deciding not to act.
“Johnny pushed me” may have been the whole story, but not likely. Why did Johnny push David? What was the context? How are the two boys connected? What’s their history? Was it a big push? Did it do harm?
Ideally, we want to know the whole situation before we decide what to say or do.

THERE’S A FAMOUS quote that’s often attributed to Thomas Jefferson: “I’m a great believer in luck, and I find the harder I work the more I have of it.”
Making your own luck is a concept I’ve long believed in, and have written about before. Clearly, luck plays a role in all human endeavors—finances especially. I’m particularly intrigued by the intersection of luck and hard work. But how exactly can we add to our store of good luck?

REUBEN KLAMER, one of my greatest financial teachers, died last month. I never knew his name until I read his obituary. Klamer invented The Game of Life—the one that’s played with a spinner, a small plastic car full of blue and pink stick people, and lots of money.

I grew up in the 1960s, long before the internet or video games. Board games were what we played when it was rainy outside or when we had family gatherings.

IF I WERE STARTING my career all over again, I don’t know how well I’d fare in today’s economy. By contrast, if my dad were alive, he wouldn’t have any trouble finding work. He was good with his hands and could fix anything. He was a machinist by trade, but he could’ve easily been an electrician, plumber or carpenter.
All the disasters we’ve endured during the past few years have created an explosion in skilled,

I SERVED ON A GRAND jury earlier this year. We heard more than 100 cases during our three-month stint. Our task was to issue an indictment if the state showed probable cause that a crime occurred. If we indicted, cases would then move on to traditional jury trials.
Some cases involved cybercrime. Others included private records subpoenaed by the District Attorney’s office from technology and phone companies, financial institutions, hospitals and commercial businesses. The experience was eye-opening.

IT’S A COMMONLY HELD belief that market risk is a function of time in the market. Simply put, risk falls as our holding period lengthens. This is the notion behind time diversification—the idea that more time allows us to diversify across different investment periods, resulting in reduced risk.
For example, the S&P 500 has historically generated positive returns in nearly every 20-year holding period, even after adjusting for inflation. Armed with this data, one of the first things financial advisors ask clients is about their time horizon.

WE’VE ALL SEEN the headlines: The tight U.S. labor market has prompted many businesses to increase starting salaries and offer hiring bonuses to new employees. But what about pay increases and bonuses for the workers who stick around, rather than jumping from one job to the next?
Like the employers who neglect loyal workers, many of us make the same mistake as we balance work and family. I’m certainly guilty. Every time I work late or take on a “side hustle,” there’s a tradeoff—less time with my family.