The Case Against Retirement That Has Nothing to Do with Finances

Peer Pressure in your 50’s?! Really? My friends and I were sitting around a table at a restaurant in Scottsdale. 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 had 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, or ran medical practices, or were C somethings – COO, CFO, CEO. We invested, saved, paid our dues by meeting payrolls, placating clients, and white knuckling through recessions with a brave face. Our homes were paid off, we had portfolio’s that had compounded daily for decades and passive income from buy out plans. So now it was that time of life for choices. And 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 skate by. I opened the desert 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 that has to work, this is a party of nine), 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? Don’t I want to take some time at the end of my life and revel in what I built? Don’t you want to wake up and know there is nothing you HAVE to do today, that you can do whatever you want? Aren’t you 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 in fact 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 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 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. 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 somehow 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 does La Jolla and the Everglades…but you know what else does? Suffering.

“So…you worked like hell 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 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 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. His most recent book is Aging Disgracefully.

Find Danny on LinkedIn, Twitter, and at &

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