FOR MOST SENIORS, purchasing Medicare Part D prescription drug insurance is the right move—even if they don’t require any expensive medicines right now. The coverage insures against the risk of someday needing prescription medication that costs thousands of dollars and might be otherwise unaffordable.

The federal government subsidizes Part D, so it’s cheaper than purchasing stand-alone private drug insurance. Another good reason to enroll in Part D at the first opportunity: You avoid the penalty associated with a late sign-up.

WHEN WE’RE YOUNG, we simplistically view our family’s money journey as one long road with clear signs that tell us to “speed up,” “change lanes” or “get off.” It’s only later, as we gain wisdom, that we can discern how messy the journey is—and how each of us ended up turning onto a different street to pursue financial freedom in our own unique way.
By exploring the money stories of three family members, I have come to better understand my own financial journey.

AS A FIRST-YEAR dental school student in 1999, when I was debating whether to apply for a military health-professions scholarship, I never gave a thought to receiving a military pension. In fact, I don’t even recall knowing that was a possibility.
I was already in debt to the tune of $65,000 from my undergraduate degree, so I was simply seeking financial aid for dental school, typically considered the most costly type of graduate education a person can buy—more so even than medical and law school.

I GOT OUT OF THE ARMY in August 1969. In the months prior, my wife and I discussed our financial plans. Simply put, if I was given a raise to $160 a week when I returned to work, we could buy some furniture for our small apartment. Bingo—we made it. I was earning $8,300 a year.

The other part of our plan was to save my wife’s salary toward a house down payment. She left the job market for good the following July,

HOME DEPOT COFOUNDER Bernie Marcus made headlines late last year with his claim that capitalism may not survive because “nobody works, nobody gives a damn.” I respectfully disagree. While Marcus has one example—people not wanting to work or work hard enough at the stores he founded—I believe America has a terrific future based on four observations:

I was a Boy Scouts leader for 16 years. I like to think that Scouts teach leadership and independence.

“I’D BE HAPPY TO JUST come here every year,” I told my husband. We and our two daughters had arrived on Maui 72 hours earlier. It was May 2000—and our first trip to Hawaii.
We’d signed up for a timeshare presentation in return for discounts on tours and activities. By the time we got to the meeting, I’d fallen head over heels in love with the place. The timeshare salesperson had an easy time persuading me to buy.

TODAY MARKS MY 300th weekly contribution to HumbleDollar. Over time, one key theme has emerged: While personal finance can be complicated, it doesn’t have to be. How can you simplify your financial life? Below are 10 ideas.
1. Tracking donations. In the old days, it wasn’t too difficult to track charitable gifts. You would simply refer back to your checkbook. But today, most people use debit and credit cards,

WHAT’S THE BEST DAY of the year to retire? Many people think it’s Dec. 31. But I used to think my ideal retirement date would be the day in February when the Cleveland Guardians played their first spring training baseball game. What better way to start my retirement than seeing my childhood baseball team in Arizona get ready for the upcoming season? When I wasn’t watching baseball, I could visit the Grand Canyon and Sedona.

NEW MORNINGSTAR research on bond funds echoes what the late Jack Bogle preached—and proved—for decades: Costs are the greatest predictor of fund performance, not stock or bond selection prowess. In investing, you get what you don’t pay for, said Bogle, Vanguard Group’s founder and creator of the first index mutual fund.

There’s a school of thought that claims it’s easier for active bond fund managers to beat their indexes than it is for their stock fund colleagues.

I WROTE MY ESSAY for My Money Journey 14 months ago. Since then, our family’s journey has continued apace—including rethinking where we live.
The highlight of the past 14 months was the addition of another grandchild. We now have four grandsons, ranging in age from five months to 10 years old. Last summer, our younger son and his wife purchased a home in Monmouth County, New Jersey, roughly an 80-minute drive north of us.

I’LL BE TURNING 65 this year, so I’ve been researching my Medicare options. Even though I work in health care—and many of my patients are on Medicare—the task of choosing a plan is no less onerous for me.
I’ve read the information provided on Medicare.gov and watched numerous YouTube videos from insurance brokers. These brokers tend to support two types of Medicare coverage. Retirees might opt for a bundle that includes Medicare Part A,

ACCORDING TO OXFORD Languages, the word invest means to “expend money with the expectation of achieving a profit.”
I like this definition better than some others because it includes the word “expectation,” which therefore should exclude casino gambling and sports betting. But what if you have an expectation of winning? Couldn’t casino gambling and sports betting both be considered investments? As Zach Galifianakis’s character said in The Hangover, “It’s not gambling if you know you’re going to win.”
How can one create this expectation?

THEY SAY THAT TAKING a cruise is a poor man’s idea of a rich man’s vacation. As an unsophisticated traveler, all I knew of cruises were the glowing reports I heard from others who had taken them—and the romanticized versions I saw in the movies.

 My aspirations were based on a movie I saw starring Doris Day, Romance on the High Seas. It’s about a glamorous, adventurous and romantic cruise with beautifully dressed people,

THIS IS MY FIRST article for HumbleDollar. I’m new to the site, but not new to writing for the public and, indeed, I’ve contributed regular columns to some small newspapers.
My life has had more twists and turns than going down a Kentucky country back road filled with hillbillies, of which I am one. Kentucky is either the poorest state in the country or next to it by any measure you want to look at.

PERHAPS YOU’VE SEEN charts like the one below, which comes from Dimensional Fund Advisors. The message: Investors who try to time the market in search of better returns often end up damaging their results. To many investors, this seems intuitive, because trading isn’t easy.
But to others, market timing appears to make a lot of sense. For instance, for years, Yale University professor Robert Shiller has been maintaining a measure of market valuation known as the cyclically adjusted price-earnings (CAPE) ratio.