How do you know someone’s retired? Don’t worry, they’ll tell you.
That’s the old joke, but it hasn’t been my experience.
99% of the time, the retirement conversation runs the other direction.
People are always asking, “What do you do?” but what they mean is, “What do you do…for money?”
Last May I posted on my retirement, mostly to crystallize my own thinking. I also wanted to make a preemptive strike on the questions I could see coming.
Clicks followed.
I thought, man, I should have done that years ago. People love reading about retirement.
As it turns out, it wasn’t the retirement part. They were interested in trainwrecks. They were interested in magical thinking. And they were interested in voyeurism.
It was just retirement. I don’t want to make it seem like I was Neo, breaking free of the matrix. For me, it was closer to Barry from Bee Movie, getting out of the hive.
“Most bee jobs are small ones. But bees know that every small job, if it’s done well, means a lot. But choose carefully because you’ll stay in the job you pick for the rest of your life.”
Lots of people put retirement at the end of their life, but I’ve got a lot of productive years left. What job would I pick if I didn’t have the financial desperation of my 22-year-old self?
Because, well, I don’t have the financial desperation of my 22-year-old self.
Progress!
But taking an unconventional retirement—the kind where you still do some work—gets a lot of eye rolls. Friends ask how “retirement” is going and they use the air quotes and everything. Puke.
But that question is a clue. A clue that they are playing a different game. They only see retirement one way.
As Naval Ravikant defines it: “Retirement starts when you stop sacrificing today for some imaginary tomorrow. You retire by saving enough money, becoming a monk, or by finding work that feels like play to you.”
Nearly everyone I know only sees that first definition. Saving enough money. But enough is a hard one to define. Even for super-smart-eye-rolling-air-quoting-“friends.”
I was after the “work the feels like play,” and for now, I’ve found it.
The best part though, once I got past the awkwardness, is when people ask me what I do.
Trevor Noah captures the situation well.
I feel like a lot of us have become a little too attached to our work, you know? We identify with our work.
Have you ever asked somebody, just randomly, “Hey, tell me about yourself?”
And they’re like “Well, I’m an architect…”
“Tell me about yourself.”
“Well, you know, I own a hair salon…”
“Tell me about yourself.”
“Well, I’m a teacher…”
“Tell me about yourself.” And people will tell you what they do. You know? It’s become the thing that people focus on.
The French don’t do that. No. You’ll never meet a French person who does that. You go up to a French person, you’ll be like “Excuse me. What do you do?”
“Oh, me? I go for walks with my friends. And, you know, I like to, you know, eat good food.”
And you’re like, “No, no, no. What do you do for a living?”
“Ah for a living? Pardon, pardon. Okay for a living, okay. No, I ah. No, I breathe, and, you know, I drink water, and you know, of course I have to make love. You know?”
I don’t live the life of a Frenchman, but I’m doing my own version. When people ask me what I do, what I’ve come to find out is they’re actually asking me what I do…for money.
Because when I tell them about my days—writing, coaching, reading, lifting—they circle back. Again, and again. They want to understand the economics. How much do you have? How much do you make?
It’s a fascinating window into how people value time.
If it gives you any idea of how I value my time, and how full the days are, I intended to write this as a retirement anniversary post. Sort of a check-in because the first post resonated with so many. But you know what? I got busy. Busy writing a book, coaching Little League, and enjoying my life. Busy traveling, having coffee with friends, and taking on new projects.
I had a few ideas and started pulling them together only to realize I’d already passed my anniversary. Retirement is just the darndest thing. You really do lose track of time. Like a kid on summer break.
Thoreau touched on this misunderstanding of time in Walden. “One says to me, ‘I wonder that you do not lay up money; you love to travel; you might take the cars and go to Fitchburg today and see the country.’ But I am wiser than that. I have learned that the swiftest traveller is he that goes afoot.”
Thoreau is suggesting that spending a day’s wage to travel by train, when you could simply set out in that direction, is a foolish trade-off. Eight to ten hours of labor for a lift to Fitchburg to see the country. How far can you walk in 8-10 hours? And how much country can you see. Go!
In modern times, people will trade weeks, months, and years of office work to afford a vacation. They work, so they can take time off work. Like a squirrel storing nuts for winter.
***
I had a few friends in high school that took on a job at the airport. They were throwing bags, loading and unloading airplanes. The hours were brutal, but it paid well, and it had a really cool perk: cheap flights.
But when you work through the night tossing bags, a quick flight to Tahoe for the weekend doesn’t have the same allure. What you really want is a nap.
These are all very common time trades, and people are getting fleeced.
Reframing that time trade is about reframing what and how much you need. Most people don’t know how much is enough. They move the goal posts so often, they can hardly believe when someone wins the game with a chip shot, or walks off the field entirely.
Leon Bean, founder of L.L. Bean, had a simple response to those that wanted him to grow his business rapidly to make more money: “I’m already eating three meals a day, and couldn’t eat a fourth.”
The Fisherman
I originally read this story in The 4-Hour Workweek and it slapped me right in the face.
An American businessman took a vacation to a small coastal village in Mexico. As he walked the pier in the early morning he noticed a small boat and a fisherman who had several large yellowfin tuna.
The American complimented the Mexican on his catch.
“How long did it take you to catch them?” The American asked.
“Only a little while,” the Mexican replied in surprisingly good English.
“Why don’t you stay out longer and catch more fish?” The American then asked.
“I have enough to support my family and give a few to friends,” the Mexican said as he unloaded them into a basket.
“But…What do you do with the rest of your time?”
The Mexican looked up and smiled. “I sleep late, fish a little, play with my children, take a siesta with my wife, Julia, and stroll into the village each evening, where I sip wine and play guitar with my amigos. I have a full and busy life, señor.”
The American laughed and stood tall. “Sir, I’m a Harvard M.B.A. and can help you. You should spend more time fishing, and with the proceeds, buy a bigger boat. In no time, with the increased haul, you could buy several boats. You’d eventually have a fleet of fishing boats pulling in yellowfin tuna.”
He continued, “Instead of selling your catch to a middleman, you would sell directly to the consumers, eventually opening your own cannery. You would control the product, processing, and distribution. You would need the leave this small coastal fishing village, of course, and move to Mexico City, then to Los Angeles, and eventually New York City, where you could run your expanding enterprise with proper management.”
The Mexican fisherman asked, “But, señor, how long will all this take?”
To which the American replied, “15-20 years. 25 tops.”
“But what then, señor?”
The American laughed and said, “That’s the best part. When the time is right, you would announce an IPO and sell your company stock to the public and become very rich. You would make millions.”
“Millions, señor? Then what?”
“Then you would retire and move to a small coastal fishing village, where you would sleep late, fish a little, play with your kids, take a siesta with your wife, and stroll to the village in the evenings where you could sip wine and play guitar with your amigos…”
I love that story. The trick is, you’ve got to know how many fish you need.
Knowing What I Know Today
“If I had my time again, knowing what I know today,” Felix Dennis writes, “I would dedicate myself to making just enough to live comfortably, as quickly as I could—hopefully by the time I was thirty-five years old. I would then cash out immediately and retire to write poetry and plant trees.”
Dennis ballparked his “comfort” at $60 or $80 million, but to each their own. Cocaine lovers need a little extra. But at least he knows his number. That is more than I can say for most.
He wrote poetry, planted trees, and published some wonderful books. Maybe he did some breathing and making love as well. The life of a Frenchman. He actually did one better—he moved to France. Purchased Mandalay Estate from David Bowie. I’m sure it was a nice place but in the back of his mind I think it was about avoiding all of that disingenuous “tell me about yourself…” he received elsewhere.
He knew how quickly people shift from “what do you do?” to “what do you do for money?”
People want to talk about the economics, not the activities. They want to understand the monetization, not the meaning. When I mention writing, the follow-up is rarely about the ideas or the craft. It’s about readership numbers, revenue streams, and growth metrics.
Sure, more of all that would be great. But the reason I write is mostly about clarity of mind. If I left all these ideas in my head, especially the bad ones, I’d go absolutely mad.
But why do people shift the conversation this way?
Money is easily measured. A way of keeping score. Do you have a good job? What most people mean is, do you have a good-paying job.
But the first rule of management, and this goes for managing yourself, is to measure what matters.
And if you’re already eating three meals a day…couldn’t eat a fourth, heading back to the office to earn a fifth and sixth seems like a strange trade.
But a common one.
Remember, your last shirt has no pockets.
So, who are you when someone says, “Tell me about yourself”? Are you your job, your bank account, your possessions?
Or are you the hikes, the meals, the friends?
The fisherman, Henry David Thoreau, Felix Dennis—they all point to the same truth: wealth isn’t about what you own, it’s about how you live. Try the French approach, or even the Fisherman’s. Tell them about the wine you sipped, the guitar you strummed, or the kid you coached. Because that’s what you really do, regardless of where the money comes from.
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