Mr. Chatterbox: How Do You Know When it's Time to Retire?

In this month's Mr. Chatterbox, Bob Plunket asks, "How do you know when it's time to retire in Sarasota?"

By Bob Plunket July 1, 2013

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I saw in the paper this morning that Barbara Walters has decided to retire, which leads to an interesting question for us boomers: "When is it time to quit your job?" Barbara quoted a song from Cabaret as the basis for her decision. "When I go, I'm going like Chelsea," meaning that when she does it, it will be once and for all, with no regrets and no second guesses. Unfortunately, she misquoted the quote—it should be "When I go, I'm going like Elsie"—thereby answering her own question: It's time to go when you can't remember what you're talking about.

I myself have been retired for almost a year now and I love it. True, I still have to write this stupid column to supplement my meager Social Security benefits, but as you can see, I am basically "phoning it in." I used to worry so about getting it right and being clever. Now I just write whatever pops into my head. Then it's back to The Price Is Right and the Jody Arias trial.

I do miss certain things about going to work every day. I miss the people—the young and attractive ones, anyway. What fun we would have during those long afternoons when the boss was out of the office, trying to sell ads or sitting in the bar at the Ritz. The younger staff members would pour out their troubles to me—their problems with the people they were dating or trying to date. Then we'd look up shoes and clothes we might want to buy online. Or check out the mug shots of people we know who had been arrested lately, and then laugh and laugh. That kind of stuff I miss.


What I don't miss are the office politics. The co-worker who's after your job, the drop in readership that's being blamed on you, that brilliant idea you had that nobody is getting behind—I can't believe all the time I wasted obsessing about such things. It was all so unimportant. Now, with my time my own, I can obsess about the things in life that really matter, like that neighbor who puts out his garbage on the wrong days or all those mysterious things about the way your cable TV is set up. I can get Channel 296 but not Channel 297. Why? Why?

You want to know what I really miss most about work? The supply closet. I haven't bought a supply in 30 years. Nowadays I invent reasons I have to drop by the office every couple of weeks, and then I leave by the back door, but only after looking both ways and slipping into the supply closet for some legal pads, pens and pencils, highlighters, folders, and maybe a new stapler, even though I never use staplers and have about 10. I also have remained very friendly with Bea, the receptionist. I've even promised her my mother's old mink coat if she'll just keep slipping my mail through the postage meter.

Here's what I've learned about retirement. It's a constant mental processing of how to spend the time you have left before you die. Do you travel? Get a new hobby? Do you get a fun job or start some interesting business? Do you spend your time eating right and exercising so you'll live a little longer? Do you stay home indoors and try not to panic? I've tried them all, and none is quite right.

But I have learned "the secret"—the thing you have to do to make it work. And it's really pretty simple.

You have to set up a situation where every day is pleasant.

This means you avoid situations that make you anxious. You don't deal with people who make you feel bad or hurt your feelings—or you just plain don't like. You don't do things you think you "should" do—like raise money for some charity you don't care about, or attend the latest play, or even follow current events. Who cares what happens in Syria? It's not my problem anymore. I'm more concerned about what I'm going to have for dinner. It's when you can finally achieve this harmonious balance in your life that you know that you are successfully retired.

And you want to know something else I've discovered? There is something about beautiful weather that makes old people feel good. That's why I'm so bullish on the future of Sarasota. This place is perfect for old people to sit in the sun. And we certainly don't need loud hippie music coming from bars downtown. Who do those young whippersnappers think they are? I've got a little high-tech business they can start up. It's called going back to wherever you came from. We don't need you here, except for heavy lifting and waiting on tables and driving us around after dark.

Yes, retirement can have many pleasures, but the most fun is figuring out whom to leave your money to. It's amazing how many people want it and how nice they'll be to you if there's a possibility they'll get it. Just look at Ulla Searing. I'll never forget the night I saw Leif Bjaland take her to the opera. He was running around like a chicken with its head cut off. He had to get her out of the car and into her wheelchair, then wheel down the aisle and get her in her seat, then wheel the wheelchair back and stash it somewhere, then run back and watch the opera—he was on the go all night.

The trick here is to keep the door open to them all for as long as you can. I don't exactly lead them on, but I do tell them that I will "help them out." That could mean anything. And don't feel guilty about doing this. Everybody does it. My own grandfather did it to me. I thought I was getting millions. And I ended up with $1,500 and a Longines wristwatch.

There is one thing they don't tell you about when to retire, though. You don't make that decision. God does. Barbara Walters discovered this when she fainted at the British Embassy. She woke up on the floor all bloody and realized, now is the time. The same thing happened to me in the parking lot at Publix. So don't plan too rigidly. The moment will come. And when it does, just try and pass out as gracefully as possible.


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