I’m often asked, “How does it feel to be retired?”
Sit down: this could take a while.
The truth is, it’s thrilling and disconcerting and reorienting in ways that I never imagined possible. It’s a complete and utter change of direction from the last 40 years of preparing, building, acquiring, ascending, enduring. Sometimes it feels like I’m flying; other times it’s a free-fall.
I’ve taken several stabs at rendering this experience in a “regular” essay, one with a beginning, a middle, and an end. The kind I’ve written a hundred times. It doesn’t work.
The experience is too different, too weird. So let’s try this instead: a series of snapshots.
The Last Good Job
I once worked at a job I loved. It had all the rewards you could ask for from a job: I liked the work; I enjoyed my coworkers (most of them); I was liked by those I worked with (most of them ); I was paid well; I had a huge amount of autonomy and control; and I was respected by our customers and by the strangers who read the content I wrote as the “voice” of our company. I could go on and on with the things that were right about this job: the commute wasn’t bad; the CEO who I reported to was smart and fair, if a little distant; I had a nice office.
Everyone should have the opportunity to work just once in a job that they truly enjoy, where they feel valued and where their labor is valued, not just financially but in human terms, where you know that your colleagues hold you in esteem and appreciate your contributions to the collective enterprise. It was good.
And then it all went to hell: we pursued and won private equity investment in the company, and it changed everything. The CEO was discharged, and a new one came in. He brought in clowns and charlatans, one of whom championed the farcical rebrand of our product as “fast, fun, and impactful.” But the work became dumb, grinding, and dispiriting. Before, we talked about building a great product; after, it was all pipeline, conversions, and EBITDA. We lost good people, hired bad ones. I tried to protect my team, but I couldn’t. Finally, mercifully, we sold the company, and on March 1, 2021, I burst from the bullshit machine, wide-eyed and disbelieving.
First Retirement
For one month, I was delirious: I read, I walked, I biked, I cooked, I watched birds. For the first time in many years all my time was my own, and the days stretched out unstructured and unbroken by meetings and phone calls and demands. No one had claims on me. I basked in time, in freedom.
Ask me then, and I would have told you that retirement was paradise.
And then, suddenly, I got bored. One night I sat out on the back porch with my buddies, all still working, and I bragged about how great retirement was, exulted in the superior life I was leading. But when they left I felt ashamed and I woke up the next day and had to admit that I didn’t know what to do with myself. My buddies all had jobs to go to, paychecks coming in. But me: I had another day where I had to figure out what to do.
I started tossing out job applications and—bing, bang, boom—I signed on as a Curriculum Development Manager at AWS. I had 14 direct reports, spread across the country: a full team developing training for AWS’s customers. Days full of meetings, one after another, and in between navigating the labyrinth of Amazon’s hiring and employee evaluation system, trying to speak this unique Amazonian language and to live the leadership principles.
What fresh hell was this? I was paid well, ridiculously well, and worked from home, but the work was of such disjointed inconsequence, done amidst rapid turnover and an atmosphere of random disconnection, that it drove me mad. The turning point came when a new director was named for our business unit ... and I could immediately see that he was a complete fool. I couldn’t live like this.
After 11 weeks in that job, I quit. Second retirement began.
And with it, the slow realization that no part of my life would be the same, perhaps ever again. All the things I had grown accustomed to, everything I had built up in terms of experience and reputation, all the armor I had put on to survive ... it all fell away.
Money
The money, of course, stopped right away. One day we were standing in the money stream, and the next day we were standing on the bank, drawing all our money from a finite pool, a supply we’d try to make last until we died.
We had prepared to step out of the money stream, of course. For the last several years of our working lives, we monitored our spending, the better to understand how much we’d need to live on each year. We figured we could make it, so we stepped out.
It’s one thing to live on a budget in theory, quite another in practice. When you’re standing in the money stream, you might spend too much on dinner, but you say, oh well, there’s another paycheck coming in. Standing on the bank, you know there’s no more coming in. You’ve got your lifetime supply of restaurant money right there, pal, and you better use it wisely.
Track Car
I had picked up a very expensive hobby during my working years: I bought a hot car and tricked it out for the race track, and then I went to the track 10 or 15 times a year. When we retired, we set aside a “track budget”—and suddenly I could count the number of track days I could afford. I started to ask myself, “Am I getting enough out of this experience to justify the expense?”
I answered that question last September, driving home after two delirious days on the track at Area 27 up in British Columbia: I’d done everything I wanted with my track car. So I sold it and pushed my remaining “track budget” chips onto the table to pay for a “bucket list” trip to Europe to drive at Spa de Francorchamps and the Nurburgring Nordschleife, two of the greatest tracks in the world.
This, I decided, would be a much more satisfying way to spend that money than just visiting the same old local tracks again and again. I’ll report back on whether that bet paid off. (See: Seduced by Speed.)
Status
It pains me to share this next bit. I feel a bit ashamed. But it’s real and I don’t want to hide it from myself: I’d been a money- and status-conscious egotist.
I liked making a lot of money. I liked knowing that I could buy pretty much whatever I wanted (with limits, sure, it’s all relative). I liked taking my kids out to fancy restaurants on their birthdays and at Christmas, I liked going on cool trips, I liked buying fitted shirts and getting the newest electronics. I admit it! It was fun.
I liked driving a hot car. Jesus, I liked that a lot! I liked it that people looked at my car, that I’d get thumbs up and nods from those who were in the know. Hell, I’d get hoots from 17-year-old kids who dreamed of driving a hot car, and I remembered I was that kid once. I liked driving that car fast on the race track—being faster than others, especially others with more expensive cars. I liked the risk-taking aspect of track driving, sure, but it also stroked my ego. I looked around and I compared my car to others and I counted myself, usually, as the winner. Disdain the egotism of driving a sports car if you like, but you I defy you to live inside a lifelong dream and tell me it doesn’t feel great. It feels great. Felt great. Past tense. I sold the car.
I liked having a high-status job. I was the Chief Learning Officer, dammit, and so what if it was at a small company that topped out at 140 employees. Our PR firm suggested the title: it would make me and the company look better, would help us place my articles in trade magazines and land me speaking gigs at conferences. I know the title was a bit inflated, puffed up, but still, I wanted that title. I felt good about it. It made me feel like I’d done something. I was a C-level executive. Big freaking deal!
I shared all this with Sara the other day, confessed that sometimes I missed the status and the money and the title, when she pointed out to me that I also had something that very few people had and that she always wished that she had. “You mattered to people, Tom. You were so lucky to have that.”
Holy shit: she was right. For a time there—before the money and the car and the title—I had something really special: I mattered, to my company and to the people I worked with. And they mattered to me. We were a small group of people who honestly liked each other and who depended on each other to elevate our small company.
I liked mattering. I can live with less money and with “regular” cars and without a job title ... it’s very possible to live a very nice life without those things. But mattering ... yeah, I miss that. I want to figure out how to matter again1. Let’s put a pin in that one, consider it a work in progress.
In the Absence of Ego ...
Strip away the money and the car and the title, strip away the job where you matter, strip away the status, and what’s left? That’s the next frontier ... that’s the land that I’m walking through now.
I took my first part time job in May. I had one requirement for this job: It had to be physical. I wanted my hands on the work, not on a keyboard; I wanted to make something. I couldn’t go to meetings, especially Zoom meetings—no disembodied, disinterested floating heads, no weirdly absent eye contact. I didn’t care what it paid; it wasn’t about the pay.
I took a job at the local bakery, known for its bread and croissants. I wanted to help with the baking, but they really needed someone who could drive a van full of baked goods down to a local farmer’s market and then “run” the booth at the market. So from May to September I ran a market stand on Saturdays and worked in the bakery one day a week. It’s fabulously hands-on: one day I sell pastries, smile and chat with people; the other day I measure and stretch and roll and pinch, digging the feel of dough in my hands. There’s beauty in the sheer repetition of it. Stretch, roll, pinch, place. Do it again. 100 times. 1000.
I took another gig in September, helping to set up and run a food service operation at the local pumpkin farm. I wanted a part-time job … but it turned into so much more than that. I worked nearly every day for the six-week season, making donuts, making fudge, scheduling and supervising high-school kids, washing dishes, and selling our goods out of this steel silo to the thousands of city dwellers who streamed into the valley to experience fall on “the farm.” Sometimes it felt like we were running a high-volume fast-food joint; other times it felt like camping.
I’m looking for the next thing now.
I read several hours a day, but I’ve canceled most of my subscriptions. I can go to the library for my reading. I’ve found myself asking for free subscriptions from Substack writers I admire. “I’m sorry,” I explain, “I’m on a limited income and I’d love to read your stuff but I can’t afford it.” Talk about having to swallow your ego! I’ve encountered nothing but grace.
I wonder sometimes what it would be like if I went even further down this path, if I took the abnegation of ego all the way? What would that look like? Perhaps I could stand on the corner and hold a sign that said “Help me find the bottom of my ego.” Yeah, that would be too much, too far.
Beyond Status and Money
So, here I am, several years after leaving the conventional working world, the quest for status and money and title are behind me. But there’s still a quest. A quest to find meaning, a quest to matter. Writing this Substack is part of this quest, and it comes with some of the same quandaries.
I’m still the same person, now that I’m retired, though I no longer swagger with self-importance. In fact, I understand now what I might have seen all along, had I not been so distracted by the chase: I am utterly unimportant and always have been. But that should not impede my search for more meaning, more mattering, more understanding. That’s the journey I’m on now. It’s the journey I’ve always been on.
Just to quell any worries about my mental health, I’m quite confident that I matter to my wife, family, and friends. What I’m talking about is a bit different than that … though I’m not quite sure yet how I’d define it.
Hey Tom -- was just thinking last Sunday that it's been a few Sundays since we heard from you!
I'm in the middle of my work day, so I could only skim. But glad to see you back. I'm certain that wherever your quest eventually leads you, it will be a success. (At first blush, I'm not sure how to reconcile the "you mattered to people" comment from Sara, and the "I am utterly unimportant... always" comment you close with. I probably have to re-read more closely, but I suspect that Sara's observations are closer to the truth...)
What a great article Tom, that was genuinely fun to read about your journey and I really appreciated it. It's a nice feeling to have played a small role in your recent life, and I have to say that I do hope we have the chance to interact again, even if just to shoot the breeze! Best wishes to you and your family, and I can absolutely assure you that you still "do matter" to a whole bunch of people!