IF MEDICARE’S A MAZE, its Part D drug plan is a maze within a maze, with no one good path and plenty of so-so choices, along with a couple of potential “gotchas.”

Until 2006, Medicare offered no coverage for outpatient drugs, so today’s situation—however imperfect—is certainly an improvement. It’ll improve even more for people with high drug costs in 2024 and 2025, as I’ll explain at the end of this article.

What if you have Medicare Advantage,

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.

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,

“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.

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,

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.

I DON’T TRACK MY finances that closely and I don’t make big financial moves very often. Partly, it’s because I’m so busy with other things. But partly, it’s because I’ve come to see the virtue in benign neglect.
Still, this is shaping up to be a surprisingly busy year. I’ve taken a handful of financial steps—with three key goals in mind:
No. 1: Prepaying retirement. Like many others as they approach retirement,

MY FATHER-IN-LAW Carson was a stereotypical engineer—organized and precise. All four of his children know the motto “measure twice, cut once.” Carson applied these traits to his finances, which he managed on behalf of himself and Mary Jean, his wife. Mary Jean depended on this.
As they aged, Carson maintained his mental acuity, but he was the first of the two to deteriorate physically. Mary Jean was strong physically but slowly surrendered to Alzheimer’s.

I WAS AT WORK WHEN my daughter called. “Grandpa was taken to the hospital in an ambulance, and you need to meet Mom and Grandma there as soon as you can.”
I entered the hospital room 45 minutes later, and I saw my mom in tears standing next to my dad’s lifeless body. Dad’s hair and face were spotted with wood chips and dirt, and he was wearing a torn flannel shirt and old blue jeans.

RICHARD NIXON IS best known for the infamous Watergate scandal. But how many of us remember that, prior to Watergate, he got caught up in another scandal over a suspect tax deduction?
In 1969, Nixon donated more than 1,000 boxes of his official papers to his presidential library and attempted to claim a $576,000 charitable deduction. This caused an uproar, and served to start turning much of the nation against the president.
Congress got involved,

IT WAS PROBABLY THE last time I would see my brother. I’m 78 and ravaged by a chronic but controlled cancer, a stroke warning and a stent. Rich is 74, with a health profile only a little less foreboding. Both of our parents died at 81.
Always cordial but not always close, we’ve worked through his resentment about how I abdicated my role as an older brother and my jealousy about his close relationship with our explosive father.

REDUCTION IN FORCE. Layoff. Redundancy. For months now, the media have been running articles about technology companies shedding workers.
In October, the headlines became personal: My manager eliminated my position. It was the first layoff in my 37-year career and an early 60th birthday surprise. My last day would be in mid-December. After another year of positive performance reviews and accompanying financial rewards, the news was a shocker.
After that fateful call with my boss,