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.

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.

WHENEVER FOLKS declare that their goal is to one day write a novel, or get in great physical shape, or learn to speak Italian, my immediate reaction is always the same: If these were things they really had a burning desire to do, they’d have done them already.
Which is why you should be skeptical of the article that follows.
Now that I’ve turned 60, I’m thinking about how I’ll divvy up my time in the years ahead.

WHEN I CLAIMED SOCIAL Security benefits, I had no idea how much there was to know—and how much I didn’t know. Bear in mind that the Social Security website didn’t exist until the late 1990s, and back then only minimal services were accessible through the site. In addition, most people didn’t fully appreciate the advantages of delaying benefits.

In my naïveté, I thought I would go to my local Social Security office to find out what options were available for claiming,

I TURNED AGE 62 LAST summer and, as with most birthdays at this stage of life, I had a pretty good, but non-spectacular day. On my birthdays, I tend to focus on enjoying the day itself as it stands before me and, for that one day, I don’t worry too much about the future, or all the adult stuff I have to do, or problems I might have to solve tomorrow, or the problems I think up in my head that would probably go away if I just stopped thinking about them.

WHEN SOME FOLKS MAKE the all-important Social Security claiming decision, one worry outweighs all others. Their big fear: The program’s funding will “run out” in a few years and therefore they “can’t depend on Social Security being around,” so the smart strategy is to claim benefits at 62, the youngest possible age.
This is not a big worry of mine—largely because Social Security won’t “go broke.” What’s happening to the program’s funding is that,

I RETIRED FROM MY other job in 2022, so I could return to our family farm. Upon leaving, one of the first decisions I had to make was whether to take my pension as a lump sum or as monthly annuity payments.
The pension plan based the lump sum on length of service, salary and age, plus the interest rate as of the prior December. The lower the interest rate at the time of retirement,

DID YOU KNOW THAT more than 500 retired ballplayers aren’t receiving pensions for their time playing Major League Baseball? It’s true.
Today, the average salary per player is $3.7 million a year and even the last man on the bench receives a minimum salary of $700,000—and yet many old-timers are getting shafted by the sport they loved to play.
The story goes back more than four decades. During the 1980 Memorial Day weekend,

IN MY ONGOING EFFORT to reduce our accumulated stuff, I was trolling through our collection of old thumb drives to see what I should download, save or toss. Among them, I discovered the 258-page presentation from a two-day retirement course that my old employer sponsored in 2006.
I wondered how the advice had—17 years on—stood the test of time. As I reviewed it, I found some excellent suggestions and some that were lacking, though I hesitate to fault the presentation’s authors.

HOW MUCH DO I NEED to save for retirement? How much will I spend in retirement? Can I live comfortably in retirement? Can I even afford to retire?
I can answer all these questions, but most likely none of my answers will be exactly right—for you. Experts tackle these questions, too, but provide inconsistent answers. Google any of them and you’ll get a range of results. Without knowing your situation, such shotgun advice is pretty meaningless.

I MESSED UP MY retirement planning—but I have few regrets.
I don’t know if or when I’ll fully retire. Arguably, I’ve been at least semi-retired for the past nine years. That’s how long I’ve gone without a fulltime job. On the other hand, during those nine years, I’ve continued to earn enough to cover my living costs and I’ve worked longer hours than at any time in my life, thanks mostly to that insatiable mistress known as HumbleDollar.

I’M ANNOYED BY the financial independence-retire early movement, otherwise known as FIRE. Most annoying are the FIRE bloggers who present their fantasy world of radically early retirement, but don’t like to be questioned, challenged or criticized. As if I’d ever do that.

FIRE folks typically have a few things in common. They were high-income earners before “retiring” and their households usually had two incomes. They’re willing—indeed eager—to embrace a frugal, nontraditional lifestyle, sometimes outside the U.S.

I’M A BIT EMBARRASSED to admit that, until I started toying with the idea of early retirement a few years ago, I was pretty ignorant about how Social Security worked. I didn’t even pay much attention to the FICA payroll taxes that were deducted from my paycheck.
As I looked into it some more, the prospect of receiving lifelong monthly checks from the government came as a pleasant surprise. I started researching how much I might get.

IN MARCH 1999, I began my job at the chemical plant where I still work today. During the weeklong orientation, I had my 26th birthday. It was the start of a job where I felt I couldn’t make any excuses. I needed to be an adult.

I would be making good money. After graduating high school in 1991, I’d averaged $18,000 to $23,000 a year in various jobs. In my first full year at the plant,

WHEN I WAS IN MY 20s, I was lucky to work for a company that offered a pension plan—and that put me on the road to retirement. Today, unfortunately, company pensions are rare. How can you ensure a comfortable retirement? Try shooting for these age-related milestones:
Age 25. Start saving at least 15% of your gross income. As I mentioned in an earlier article, a Fidelity Investments study found that if you save 15% of your gross income every year from age 25 through 67,