March 31 was a big day for my friend, Sandra. When you read this, she will be one of the few, the proud, the voluntarily retired. I know this because she’s been making her friends look at the retirement countdown on her phone daily. Sometimes more than that. And once in a while, we’ll even ask to see the latest spinning numbers.

It doesn’t seem possible that one of my pals is old enough to walk away from her 8-5 gig and live a life of leisure. Sandra’s been working since she was a teen (I think that was before child labor laws. Like 1911, right, Sandra?), so what a sweet achievement.

My retirement date looks pretty dim and far-off from the cheap seats here in nearly double nickel land, but if the stock market is willing and my children eventually move out for good, there’s a decent chance I may retire before 82.

It wasn’t always this way. Working for a small business in my twenties and then co-owning that small business in my thirties did not equal a 401K or any retirement savings whatsoever. We were just happy we could get paid regularly.

Making a move to be the director of a tiny nonprofit would usually mean more of the same. Fortunately, my particular nonprofit is a program of a community college. Behold the State of Wyoming benefits!

Retirement can be such a fraught word – inducing longing, fear, sadness, anticipation, disappointment, or celebration. I’ve seen some combination of these emotions occur in the first month of retirement! It’s such a huge adjustment. Your schedule, focus, and plans are all upended, and it’s now up to you to decide on what and with whom you spend your time. This can be felt as exciting freedom or scary as hell.

When my parents retired at 60, they never looked back. It was apparent, almost instantly, that they were twice as busy as when they were working. How was this possible? They had forty hours devoted to work alone. How did they get it all done before? They weren’t sure either, but no time to talk! They were busy! And happy. They loved planning their free time and filled it with activities they enjoyed.

On the other hand, my dad’s best friend is still a practicing attorney in his 80s and will leave his law office feet-first. Practicing the law is who David is; his life and his profession intertwine. For others who work in occupations with mandatory retirement ages, many aren’t ready for the push out the door, leaving them rudderless and questioning their identity.

With the advent of the Great Resignation and the upheaval of ‘typical’ work as we know it, how people view their employment (and thus, their retirement) is in flux too. Sandra and I have had steady jobs our entire adult lives, assuming that we would be able to stop working if we’d been fortunate enough to amass the funds to make that happen. Those on more flexible schedules, who work from home, can travel with their job, might not see retirement as a natural conclusion.

Here are some things I know about myself that will serve useful if and when I’m able to retire. I will need to have plans, trips, classes, and other scheduled events to structure my time. If I have days left wide open for the foreseeable future, there’s an excellent chance I won’t get out of bed. Ever. The more I have going on, the more I will get done. I always thought that if I were home all day, I’d clean out all the closets, organize my zillions of photos, and have a color-coded junk drawer. During the Covid-enforced stay-at-home, I did none of those things. I need a deadline, not endless time.

I will also plan as much travel domestically and abroad as I can afford until I want to stay home. Since my kids were born, I haven’t been abroad, and it’s starting to chafe. Get ready, passport! You’re going to get stamped and stamped often!

Whether retirement means reinvention, relaxation, or recalibrating, it’s worth thinking about what yours may look like. I’ll close by quoting one of my daily New Yorker cartoons that obligingly appeared today. A man is at his retirement party and has been asked about his future. He replies, “No plans set in stone yet, but I’ll probably spend some time getting on my wife’s last nerve, maybe hyperfocus on the lawn.”

Indeed.