I NEVER PLANNED TO retire at age 53. I wasn’t an early adopter of the FIRE, or financial independence-retire early, philosophy. In fact, I didn’t start saving seriously until my late 30s, when I left my first husband and finally realized that—unlike pensions in my native U.K.—my U.S. pension didn’t come with an annual cost-of-living adjustment.

Instead, three developments in the late 1990s led me to consider quitting. First, I was no longer enjoying my job.

ONE RECENT TREND among newly minted retirees: unretirement. According to an AARP study, some 3% of retirees are back in the workforce one year later, taking on either fulltime or part-time jobs. Often, unretiring wasn’t part of the retiree’s original plan—but we shouldn’t assume it’s necessarily about needing money.
Starbucks’s Howard Schultz, quarterback Tom Brady and Disney’s Bob Iger are poster children for unretiring. Even our HumbleDollar world includes many examples of those who have reinvented,

AS FOLKS HURTLE toward retirement, they often wonder whether they’ve saved enough, debate when to claim Social Security and fret about how they’d pay for long-term care. Make no mistake: Such issues are hugely important.
But amid these financial musings, we should also spare a thought for four other questions:
How can I transform myself from a diligent saver to a happy spender? This sounds so easy, and yet many struggle with it,

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.

MANY RETIREMENT savers fund tax-deferred accounts—with good reason: The money we contribute pre-tax to an IRA or 401(k) reduces our taxable income, plus that money grows tax-deferred until withdrawn.
But there are two lesser-known benefits that are worth keeping in mind. First, with IRAs and solo 401(k)s, you can contribute for last year right up until the tax-filing deadline in April of the following year. That means you can calculate your tax bill, make an IRA contribution that’s credited to last year—and voila—cut the tab you owe Uncle Sam.

WE BEGAN IN 2019 to think seriously about what we wanted our retirement to look like. My husband had retired in 2018. I was aiming to leave my job in 2022. We were hoping to have a plan in place long before my final day of work.
Our first step was to decide where we wanted to live. We were both eager to escape the Pacific Northwest, so we zeroed in on a couple of potential destinations.

RECENT HUMBLEDOLLAR articles have addressed issues of aging, including defrauding the elderly, end-of-life considerations and preparing our homes to age in place. It must be the season for worrying about the elderly because I’ve also had their welfare on my mind, thanks to several recent events.
First, a friend’s 93-year-old mother fell down a flight of steps in her home. A faulty handle came loose from a door at the top of a staircase,

AH, RETIREMENT. You’re blissfully free of the daily grind. If you’ve made plans for this long-awaited milestone, great. What if you haven’t? You may feel out of sync and out of sorts.

I’ve heard it said that, “The capacity to take a fresh look at all things makes a young person out of an old person.” It’s never too late to look anew at the challenges of retirement, while you still have time to resolve them.

I RETIRED ON MAY 27, 2022, which was my 55th birthday. I chose my birthday because it was the earliest date I could leave my job and still be eligible to receive the early retiree health-care benefit offered by my employer.
Mentally, I was ready to go. I’d been employed at a small liberal arts college for 24 years. I’d been there long enough to see an almost complete turnover of the faculty and staff in my department.

I COULD BE KIND TO my home and say it has rustic charm, but that would be pretentious. The truth is, it’s an old house, built in 1930 by my maternal grandparents. It sits on a remnant of the farm my family once owned. It’s a place I love, and where I’d like to grow old, and therein lies the challenge.
More than 20 years ago, my father and I extensively renovated the house inside and out.

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,

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,