GETTING TO RETIREMENT is lazy work for an indexing aficionado. What could be easier than stuffing money every paycheck into an all-in-one target-date index fund? Even building a two- or three-index-fund portfolio takes minimal effort.
Actually retiring, on the other hand, feels like a fulltime job. Who knew that spending money takes more thought than earning, saving and investing it? At age 61, I’m faced with important decisions that I want to get right,

I WROTE MY FIRST article for HumbleDollar in 2017. I’d been retired for nine years and I had plenty of material. I’d made a lot of mistakes with my money over the years.
I was truly a humble writer then, and I still am. My early articles weren’t my best. It was a learning experience. I wrote them using the notes app on my old iPhone 5—an app that was designed for jotting down quick thoughts,

WHEN I WAS FORCED out of my banking job of 36 years, I was age 59 and had enough money to retire comfortably. But I still felt the need to work—because that’s how I’m wired. Working gives me a sense of purpose and makes me happy, but it has to be the right kind of work.
I need work that’s fulfilling and which allows me to help others. I knew myself well enough to realize that,

“HOW MUCH CAN I withdraw from my portfolio each year?” It’s one of the most common questions that retirees ask.
In the past, I’ve talked about the 4% rule, a popular tool for addressing this question. Among the reasons it’s so popular is its simplicity: In the first year of retirement, a retiree withdraws 4% of his or her portfolio, and then that amount increases each year with inflation. If you have a $1 million portfolio,

NOW THAT I’M RETIRED, I have more time to reflect on the larger shape of my life—a tendency that’s lately been strengthened by the fairly common impulse to ponder what to accomplish in the new year.
The disturbing truth: An objective assessment of my life suggests I’m pretty boring. Of course, I’d long known that most other people were boring. But until recently, I hadn’t realized I was one of them.
I also didn’t realize that my capacity to enjoy what looked from the outside like a boring life is,

I EXPECTED TO SPEND early 2017 blogging about my fourth round-the-world trip, which I’d just completed, and planning my next journey. Instead, I spent much of the year on the couch with a heating pad, in between assorted medical appointments, everything from acupuncture to meeting with an infectious disease specialist.

Eventually, I got a definitive diagnosis—I had a form of rheumatoid arthritis—and, in early 2018, an effective medication. But I had been forcibly reminded of something I’d first learned 10 years earlier,

I RECENTLY DISCUSSED Social Security with a friend. After trying to explain the program’s funding, I gave up when his reply was, “The facts are that the Social Security money was misappropriated and there’s no way it can be tracked after all these years. People die before they collect one Social Security check, and others get very few checks. You will never convince me otherwise.”

Yes, that’s the one thing we do agree on: I will indeed never change his mind.

WHEN I RETIRED, I thought a successful retirement was primarily about money—about making sure I had enough income to fund daily expenses for 30 or more years. But now that I’m in my 70s, my investments don’t seem quite so important to me.
Indeed, other things in my life strike me as just as crucial as my investment portfolio’s size. Some say retirement is like a three-legged stool. No, not the traditional three-legged stool of personal savings,

WHEN I FOUND myself unexpectedly packaged off by the bank, I was initially very happy. I was planning to leave anyway because the stress was getting to me. When the bank gave me a severance check at age 59, I felt like I’d won the lottery.
Life was pretty good for a while, but then I was hit by a bad case of retirement shock. I lost my mojo, and had a constant feeling of being incredibly lost and vulnerable.

THE BEST DESCRIPTION for my career would be “corporate vagabond.” I moved the family six times to five different states over 42 years.
Because we never settled down in one place, my wife and I spent 15 years visiting potential retirement locations. We visited sprawling metropolitan areas, small towns, retirement communities and the town where we both grew up. We also considered the areas where we’d lived, but nothing appealed to us.
One evening,

RUNNING OUT OF MONEY is retirement’s biggest financial risk—though this, of course, never actually happens. Thanks to Social Security, almost all retirees will have some monthly income, no matter how long they live.
Still, Social Security alone probably won’t make for a comfortable retirement, though it is the financial cornerstone for many. In fact, Social Security accounts for at least 50% of income for half of retirees. That includes a quarter of those age 65 and up for whom their monthly benefit is at least 90% of their income—a statistic I find shocking.

AT A DINNER THAT I attended recently, someone pointed out that a high percentage of us were newly retired. That included me, as well as a couple who were just reaching age 60. After the dinner, the wife of the couple told me she was offended by being called retired. She’s writing fiction every day and her husband does some consulting work.
The work they’re doing pays, but it’s not by itself enough for them to live their comfortable,

WE LIKE TO ESCAPE the Northeast’s cold each winter, so we just spent 10 days in Sarasota, Florida. Like many others when they’re on vacation, we found our noses pressed against the windows of real-estate offices, perusing the listings and musing about whether we’d want to live there.
Fantasizing about the future is fun and free, but it can also be dangerous. It’s how folks end up buying timeshares and second homes during wonderfully relaxing vacations.

I JUST GOT A RAISE from Uncle Sam—and relief from one of early retirement’s biggest unknowns.
In December, when I turned age 65, I swapped my bronze-level Affordable Care Act policy for Medicare plus a Medigap policy. My wife was already on Medicare. Compared to 2020, when neither of us had Medicare coverage, our monthly cost today for health insurance is $684 lower.
My calculated risk has paid off. As a young adult, I set my sights on early retirement.

I JUST READ THAT the 4% rule is making a comeback. From where, I thought?

Under the 4% rule, you withdraw 4% of your nest egg in the first year of retirement. If you had $1 million, you’d take 4%, or $40,000. In year two, you’d add inflation to your previous year’s withdrawal. Say inflation ran at 6%. You’d multiply $40,000 by that 6% to get the second-year adjustment of $2,400. Add that to the prior year’s $40,000,