Peer pressure in your 50s? Really?

My friends and I were sitting around a table outside of a restaurant in Scottsdale. There were no bugs, no wind, no humidity. It was 75 degrees and perfect. People who retire to Florida have simply never been to the West Coast.

Eventually, the conversation turned to a common question: “What’s your plan?”

My friends and I will get little sympathy. I’ve read the reports that roughly a third of Americans have no savings, but that’s not us. We all owned businesses, or ran medical practices, or were C-somethings – COO, CFO, CEO. We invested, saved, and paid our dues by meeting payrolls, placating clients, and white-knuckling through recessions with brave faces. Our homes were paid off. Our portfolios had compounded daily for decades. Now, it was time for a life for choices.

What were our plans? Around the table we went: Travel (Italy and Israel the big winners here). Ski resorts (the Alps and Colorado). Second homes and boats. Going back to school. Starting a charity. Learning a language. A trip to wine country. Or a wine cellar. Or just ordering more wine.

I sat in silence and hoped I might sneak by. I opened the dessert menu and pointed out that the chocolate choices are often coupled with comic book movie terms: “Rogue Chocolate.” “Depraved Chocolate.” “Death by Chocolate.” But the diversion failed.

“What’s your plan, Danny?”

I shrugged, said the topic was boring. But you know how peer pressure works. The more I tried to deflect, the more they asked. When I said I’d rather not say and reached for the check – thinking, This has to work; this is a party of nine – we all suddenly turned 16 years old again. It was like wasn’t willing to talk about how far I’d gotten in the back of my car with my girlfriend’s clothing.

“Oh, we’re not good enough? Your plans are so beyond our capacity to understand? We can share, but you get to …”

“I don’t have a plan, okay? Everyone happy?”

This made no sense to anyone. Didn’t I want to travel? Didn’t I want to take some time at the end of my life to revel in what I had built? Didn’t I want to wake up knowing there was nothing I had to do? That I could do whatever I wanted? Wasn’t I tired?

dominos“Hmm. No, no, no, no, and, uh, no. Can we leave it, please?”

But no, we couldn’t leave it. They wanted to know more. They weren’t judging, just curious. Whether it was the hour, the wine, or the fact that I knew none of us would have been successful in life if we hadn’t judged everyone all the time, I told my friends the truth:

“I don’t want to travel. I have traveled nearly every week of my life building my company. The last thing I want to do is travel. You can all have my miles.

“Waking up in the morning with no plan other than where and when to eat dinner scares the crap out of me. When did you guys start living for food? You talk about food all the time!

“I may be the first baby boomer to retire to New York City. It’s only a grind when you have to work for a living. To be there when all I have to do is walk, people-watch, see shows, go to museums, and absorb energy seems as much a paradise to me as being in a development with a private beach and a golf course is to you.

“Speaking of golf, we mostly suck at it, and you guys somehow think as your bodies age you will get better at it because you can do it more often now. You won’t. You’ll suck more, and the sun will drain your remaining life force. You’ll play 18, take a nap, go to dinner, and fall asleep during the movie you paid half price for.

“I don’t live for good weather. I like the cold. I like how it challenges you to respond to it. I have never been freezing and exhausted at the same time. I know the desert has a ‘certain beauty,’ as do La Jolla and the Everglades, but you know what else does? Suffering.”

“You worked like hell all your life so you could suffer?”

“No. Yes. Intermittently.”

“You want to keep on working at the office?”

“Why is that so crazy? I like my office. I like the young people in my office. They don’t talk about how they feel all the time. They don’t compare everything that happens in life to something that already happened.”

“That’s the plan? Die with your boots on? Working?”

“I don’t have a plan. I only think about it when I see you guys. But no, I don’t want to die at the office, if only because it would be embarrassing. I want to die in my bed, reading a book. And I want my last words on earth to be, ‘I didn’t know that.’”

There was silence while I signed the check and pocketed my credit card. I gave the group the “whatever” shrug, and one friend’s wife said: “Our plans are much better than yours. Just saying.”

Danny Cahill is president and managing partner of Hobson Associates. His memoir, Aging Disgracefully, came out this may. You can find him on LinkedIn and Twitter.

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