I’VE DECIDED UPON MY retirement date: July 1, 2025. We just passed the one-year countdown point, so I thought I’d share some of my ideas and plans for my final year in the workforce.
This countdown idea, of course, isn’t original with me. Indeed, there are apps that you can put on your phone to count down the time until retirement. I was primarily inspired by a retirement blogger named Fritz Gilbert. He’s way more decisive than I am.

DURING MY INSURANCE career, I worked for a company that focused solely on certain types of businesses, or what’s known as niche underwriting. One niche was called senior living, and it insured continuing care retirement communities, or CCRCs.
These communities typically consist of apartments where retirees live alongside an adjoining nursing home. One benefit: When residents need nursing home care, it’s right next door. If they’re married, the healthy spouse can just walk to the nursing home to visit his or her beloved.

THESE DAYS, IT SEEMS every other article on retirement talks about a neat division between the go-go, slow-go and no-go years, with retirees moving seamlessly from one to the next.

I don’t remember seeing anything about these stages back in the late 1990s when I was contemplating early retirement. Instead, when I quit full-time work in 2000 at age 53, I just wanted to travel before I got too decrepit.

I did travel—extensively—right up until 2017,

RETIREMENT BRINGS with it a host of questions. The No. 1 question: Do we have enough for a financially comfortable retirement?
It’s an issue that’s no longer relevant to me, but it’s certainly relevant to my wife Elaine and to almost all HumbleDollar readers. But that fundamental question is just the beginning.
There’s a host of other retirement questions we ought to ask ourselves—about whether we have the right investment mix, how we’ll spend our time,

I RECENTLY READ AN article by Anna D. Banks, an executive coach and human behavior consultant, who talks about the importance of cultivating friendships in retirement. She discusses embracing new activities, volunteering, reconnecting with old friends, using technology, attending social events, and being open-minded about forming friendships with people from other backgrounds.
All this got me thinking about HumbleDollar.
The Breakfast Club is a coming-of-age movie from 1985—a movie,

I’M NOT PARTICULARLY well traveled. I’ll turn age 65 at the end of this year and I’ve never been to a Caribbean island. I’ve never been to Hawaii or Bermuda. Heck, I’ve never even been on a cruise.

I’ve never been to Canada or Alaska. I’ve been to a couple of the U.S. National Parks, but have yet to visit the Grand Canyon, Yellowstone and Yosemite. 

I’ve been to Europe quite a few times,

MY WIFE AND I HAD intended to live in our single-family home for the rest of our lives. We remodeled several times so we could age in place, and we were confident we were all set for the future.
We knew life could change in an instant. We just didn’t think it would happen to us. My wife fell at home four years ago and suffered a traumatic brain injury. After six months in hospitals and rehab,

WHAT DO WE MEAN BY an “enjoyable” retirement?

I suspect there are as many answers as there are retirees. But one thing remains a constant: the need for an adequate income. Given a choice, I don’t think many people would choose to live a frugal, barely financially sufficient retirement.

My father retired at age 66. I say “retired,” but the reality is one day the owner called him into the office and said he was no longer needed.

JEFF, DAVE, JERRY, Glenn, John, the ElderBeerMen, and then Jeff again. Experts say a robust social network is crucial to a happy retirement. My life’s journey has revolved around a handful of friends who begin and end with the same good dude. 
I was a 15-year-old kid who didn’t like school, and I had the grades to prove it. I did, however, have two burning desires. I couldn’t wait to turn 16 so that,

DO YOU REMEMBER the days before you could drive? You felt like you were on a leash. No freedom. No fun.
I have news for you: Those days could return.
One of the post-age-65 nightmares that we don’t talk about enough: Most affluent retirees live in the suburbs. Homes are miles from grocery stores, medical offices, movie theatres, restaurants and—perhaps most important—drugstores.
In the suburbs, the stream of city-based public transportation usually slows to a trickle.

I’VE BEEN MARRIED TWICE, yet neither time could I take my newlywed wife on a proper honeymoon, let alone a lavish one. Hearing the honeymoon stories of others always left me feeling wistful, tinged with a hint of envy.
My first marriage was a bit rushed. My first wife—now my ex—and I wanted a no-frills civil marriage followed by a simple reception. But my parents insisted on a traditional Bengali wedding with its array of rituals,

I HAVE A FRIEND—we’ll call him Dave—who retired from Wall Street perhaps eight years ago, when he was in his early 50s. Soon after, he designed a sailboat and had it built, and he’s been sailing around the world ever since. In fact, judging from his Instagram updates, Dave is now on his second or third self-designed boat. Or is it a yacht? I don’t know anything about sailing.
At this point, you may be sighing with envy.

I’VE OFTEN BEEN TOLD that I’m too direct. To me, “direct” means to focus on the facts, get to the point, eliminate the fluff, keep matters as simple as possible.

Guilty as charged.

Think of all the time wasted by fluff. After making something more complicated than necessary, somebody is ready to provide a solution to what may or may not be a problem. Fluff thrives on confusion. It can scare folks unnecessarily. Most Americans don’t know how to deal with financial fluff.

MY RETIREMENT BUCKET list includes long drives across the U.S. in search of the unexpected.
Such trips appeal to my frugal nature. As a rule, the total cost of gas, hotels and meals is usually less than the total for roundtrip plane tickets, airport parking fees and baggage expenses. This might not be true for single travelers. But it’s a guideline that works for my wife and me.
We typically pack peanut butter and jelly sandwiches,

WE’RE IN OUR SECOND year as nomads, having sold our Texas home and driven away from our storage unit in November 2022. In the few years before that, we often talked about where we wanted to move, but could never quite decide.
When I retired in 2021, we traveled for most of the next 12 months. At the end of it, we still hadn’t decided where we wanted to live, but we knew we wanted a change,