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Wednesday, October 28, 2026Oct 28

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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.
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. 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.