Photo: Deposit Photos

By Danny Cahill

Peer pressure in your 50s?! Really?

My friends and I were sitting around a table at a restaurant in Scottsdale, AZ. The table was outside. Because there are 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.

The conversation quickly devolved into a question: What’s your plan?

I know my friends and I will get little sympathy.

I have read the Go Banking survey that says 30% of baby boomers have zero retirement savings.

But that’s not us.

We all owned businesses, ran medical practices, or were C somethings—COOs, CFOs, or CEOs.

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, we had portfolios that had compounded daily for decades, and passive income from buyout plans.

So, now it was the time for choices. And around the table we went: travel (Italy and Israel the big winners here), ski resorts (the Alps and Colorado), second homes, 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 that I may skate by. I opened the desert menu and pointed out that the chocolate choices were 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 and said the topic was boring. But you know how peer pressure works. The more I tried to deflect, the more they asked. I said that I’d rather not say and reached for the check (thinking this has to work, we’re a party of nine). And suddenly, we were all 16 years old, and I 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?”

I was asked to elaborate. 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 and revel in what I’d built? Didn’t I want to wake up and know there was nothing I had to do that day? That I could do whatever I wanted? Wasn’t I tired?

“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. So, whether it was the hour, the wine, or the fact that I knew none of us would have been successful in life if we didn’t judge everyone all the time (and done it well), I told them the truth:

I don’t want to travel.

I have traveled nearly every week of my life while building my company. The last thing that I want to do is travel. You can all have my miles.

Waking up in the morning with no plan

Waking up in the morning with no plan other than where and when we are going 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

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 the 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

Speaking of golf, we mostly suck at it. And you guys somehow think that as your bodies age, you will somehow get better at it because you can do it more often. 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 that you paid half-price for.

I don’t live for good weather

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 does La Jolla and the Everglades … But you know what else does? Suffering.

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

“No. Yes. Intermittently.”

“So … 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 has already happened.”

“So 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 them the whatever shrug and one of my friend’s wife said: “Our plans are much better than yours. Just saying.”

Danny Cahill is the author of Aging Disgracefully. He started his career at the headhunting firm Hobson Associates straight out of college. He was its rookie of the year and subsequently its youngest top producer and its youngest manager. At twenty-seven, he bought the company and built it into one of the country’s largest privately held search firms. His success led to a speaking career that culminated in being awarded the recruiting industry’s first (Knutson) ”Lifetime Achievement Award.”

In his other life as a playwright, his works have been produced off-Broadway and he has won the Maxwell Anderson, Emerging Playwright, and CAB theatre awards. His first book, Harper’s Rules, won an Axiom award.

For more information go to Hobson Associates and According to Danny