THE GOLDEN YEARS of life are often heralded as a time of relaxation and freedom, but for many, this period brings with it the daunting complexities of health care management. My journey through the labyrinth of Medicare Advantage and the elusive Medigap plan is a testament to the challenges faced by countless seniors across the nation.
The Allure of Medicare Advantage. Initially, the promise of Medicare Advantage seemed like a beacon of hope.

COULD HUMBLEDOLLAR be replaced by a website chock-full of articles created using artificial intelligence? The short answer: It would be remarkably easy—and I fear readers wouldn’t object, especially if they didn’t know how the articles were generated.
To show what’s possible, I requested eight personal-finance articles from three freely available artificial intelligence (AI) tools, ChatGPT, Google’s Gemini and Microsoft’s Copilot. The first of those articles is published today, with the other seven appearing over the next four days.

LIFE HAS A CURIOUS way of presenting us with unexpected opportunities for growth and learning. For me, one such moment occurred during an ordinary workday when I found myself trapped in an elevator with none other than Jack Bogle, the iconic figure in the world of finance and founder of Vanguard Group. Little did I know that this unforeseen predicament would lead to a profound exchange of ideas and invaluable investment lessons.
The day had started like any other,

I’VE NEVER BEEN MUCH of a collector. As a kid, I tried collecting comic books for a short time. I found that, after I read them, I had little use for them. I stored the comic books in an open box in my closet, where their translucent sleeves attracted a thick blanket of dust but little interest.
Later in life, I started a small wine collection. I didn’t get too far. It turns out I drank the wine at a rate far quicker than I acquired new vintages.

THOSE WHO REGULARLY read posts on Bogleheads.org—and I’m guessing a good chunk of HumbleDollar readers do—know that the Bogleheads’ philosophy is to:

Never time the markets.
Buy only broad-market index funds via either mutual funds or exchange-traded funds.
Invest 25% to 75% of a portfolio in stocks using such funds, with the rest in bonds, and thereafter rebalance as needed. How big a percentage should you put in stocks? That’s based on risk tolerance.

I’VE BEEN WRITING FOR and reading HumbleDollar for more than six years.

I’m struck by the number of articles and comments that talk about things like divorce, job loss, health issues, adverse financial events and caring for elderly parents.

When articles discuss such experiences, the pieces are typically well read, with numerous comments, including many expressing empathy. The amount of personal information shared is amazing. No doubt readers can relate to many of these events.

THERE SEEM TO BE four subjects that folks are reluctant to discuss with acquaintances, friends, intimates and often themselves: money, sex, religion and death. A few months ago, I broached the subject of money, to wit, my investment history—territory well-trod by this readership.

I will now turn to the literal and figurative last item in the above lineup of forbidden subjects: death. As a physician, I have some knowledge about the death of others.

THIS IS MY 150TH article for HumbleDollar. My first appeared on Aug. 12, 2019. I’m not sure when I became aware of the site, but it’s become an important part of my life. I’ve truly enjoyed the writing, along with reading the work of others and interacting with the editor, other contributors and readers.
For my 150th, I thought about looking back over the past five years and compiling a list of 150 observations.

WE BOUGHT A SAILBOAT and trailer in 2008 for our son for his 15th birthday. At the time, he was too young to own a boat, so I registered it in my name.
Fast forward 15 years, and we finally got around to transferring the title to our son. Transferring the boat was quick and easy. Transferring the trailer was not.
Cars, trucks, boats and trailers all have unique vehicle identification numbers, or VINs.

“I CAN’T GET DIVORCED.”
“But Randy, I thought you guys were moving toward one.”
“I mean, I can’t afford to. I just went to see my accountant and a lawyer.”
“And?”
“Remember, California is a community property state. Even though I made almost all our money, Sarah’s entitled to half of it. I know she was dedicated to raising Harris all those years, but wow, Steve, I’m cooked.”
“But you were such a sought-after internist.

I’M A TERRIBLE READER. I have been my entire life. This was very upsetting to my mother, who felt reading was the key to success.
In fact, my entire family were great readers. Sunday’s New York Times was a fixture in my parents’ house. They’d spend hours reading every section. I hated it.
My father was born in the Hell’s Kitchen section of New York City. He attended Purdue University, studying chemical engineering,

IN THE INVESTMENT world, there’s no shortage of data. But how useful is all that data? To help get to an answer, let’s consider four questions:
1. When the economy is strong, is that good for stocks? The simple answer is “yes.” According to textbook finance, the value of any company should represent the sum total of its future profits. When the economy is strong and profits are higher, that should be good for stocks.

OUR RETIREMENT INCOME is built on a slew of financial products and strategies. But we should think less about the gory details of each—and more about the role they play in our overall retirement finances.
The fact is, while each of us comes to retirement with different levels of wealth and different desires, we all want both a sense of financial security today and confidence about our financial future. How can we best meet those twin goals?

LET ME PLAY THE contrarian. A dominant narrative today is that—compared to earlier generations—younger workers are both economically disadvantaged and less inclined to do anything about it.
Such notions have been bandied about for at least 2,000 years. Horace wrote that “the beardless youth… does not foresee what is useful, squandering his money.” For a more modern take, check out these comments from HumbleDollar contributors and readers lamenting the financial plight of today’s younger generation:

Company “loyalty to employees in large measure no longer exists.”
“Young people are forced to contend with the twin challenges of relatively low salaries and high student loan burdens.”
Baby boomers are “fortunate in a way that’s nearly impossible for Americans today.”
“Many workers are strapped today,

AS A KID, I WAS usually one of the last chosen for pickup games, be it softball, basketball or football. My athletic prowess was limited to being the fastest kid in my neighborhood, but it seems I lived in a slow neighborhood. I had moderate success on a local swim team, but again found that success didn’t translate to surrounding communities.
Into my teen years, I was plagued by allergies and asthma. It wasn’t until the late 1970s,