Kennedy: Deciding when to retire is not as easy as it sounds

Staff file photo by Olivia Ross / Columnist Mark Kennedy says he has no immediate plans to retire now that he's turned 65, but having friends his age no longer in the workforce leaves him feeling a little pickleball envy.

My Facebook feed is filling up with photos posted by retired friends who seem to be on perpetual vacations.

One high school classmate appears to live on a cruise ship. Another stopped by to see me on his way home in upper East Tennessee from a midweek Braves game earlier this month.

For context, I turned 65 this year, so a lot of my peers, who were also born in the late 1950s, have begun retiring.

Suddenly, I'm feeling a little pickleball envy.

I guess you could say I've started taking baby steps toward retirement. I'm signed up for Medicare — which, by the way, has more complex moving parts than a rich man's Rolex.

I also met with a financial expert last week who talked me through some investment options. (Among the sexy topics we discussed: Immediate annuities, friend or foe?)

(READ MORE: Why near-retirees are terrified to look at their investments)

I'm not one of the 49% of baby boomers currently working who say they expect to work past 70, according to a recent survey by the Transamerica Center for Retirement Studies. Although I would enjoy working part-time for as long as my health allows, I'd rather not die while still punching a clock.

Also, I don't want to die while making the virtuous choice to "optimize Social Security" by delaying benefits until age 70. Chasing perfection is America's silent killer.

I guess I always thought this retirement thing would ultimately be a dictate, not a choice. In an industry famous for downsizing, job loss was always a possibility. Also, when you crest 60, personal health is a wild card that could sideline you at any point.

Either of those scenarios could still unfold for me, but it looks more and more likely that the choice of when to retire will be a matter of personal preference. That's great, but it's also scary.

There are family considerations. With one son who's a senior in college and another who's a junior in high school, our "nest" is in transition, but it's not yet empty.

Meanwhile, inflation is making nest-egg drawdowns more scary, and calculating my life expectancy based on family history makes me feel extremely mortal.

When I was 11, my dad offered me $2 to dive head first off the high diving board at the swimming pool at David Crockett State Park in Lawrenceburg, Tennessee. I walked to the end of the diving board at least five times before I took the plunge, and the next thing I remember was the water's surface punching me in the face.

The punch in the face this time will be leaving a profession I adore. For most of the last 30 years I've written a regular newspaper column that allows me to meet interesting people and share my observations. Newspaper columnists were influencers before we even knew there was such a thing. It's always felt like a precious privilege to me, and it will be hard to let go.

Still, there's something liberating about knowing you could retire at any time but continuing to work for fun. For most of our lifetimes, we boomers have worked our jobs like our lives depended on it. (One of our problems, I guess, is that we have not sufficiently differentiated between our lives and our livelihoods.)

I teach a journalism class at UTC, and the other day one of the students pitched a story about Gen Z's tendency to ditch jobs that didn't offer a good work/life balance.

(READ MORE: Gen Z and Baby Boomers are more alike than you'd think)

I asked: "Raise you hand if you've ever quit a job because you thought it was too demanding."

More than half the students raised their hands.

Not to overgeneralize — I've worked with and taught some amazing Gen Z journalists — but maybe America still needs a few of us never-say-die boomers sprinkled through the workforce for stability.

Or at least that's what we oldsters like to tell ourselves.

Meanwhile, some of us are still on that retirement diving board waiting for our courage — or a big gust of wind — to send us over the edge.

Contact Mark Kennedy at [email protected] or 423-757-6645.