Why I Will Never Retire. And Why the Premise Itself Might Be Wrong.
Greetings,
June’s pre-order incentive for my book Real Wealth is now live. Pre-order this month, tell me you did at tylergardner.com/book, and I’ll send you a three-part exclusive podcast series—the unfiltered version of my own financial story that didn’t make it into the book. The mistakes, the pivots, the moments that actually shaped how I think about money. Delivered digitally in early July. Pre-order now and you’re also locked in for every monthly incentive through the December 1st release.
Here are the 5 Reasons Why I Will Never Retire. And Why the Premise Itself Might Be Wrong.
1. Retirement used to make actuarial sense. It no longer does. The retirement system was designed in 1935 when the average American life expectancy was around 62 and the retirement age was 65. The system was designed, quite deliberately, around the assumption that most people would not survive long enough to enjoy it. This was either very practical or very dark depending on your disposition, but either way it has absolutely nothing to do with your life in 2026.
We are now routinely looking at twenty to thirty years of post-career life. Twenty to thirty years. I like pickleball. I enjoy a good walk. I have bloodhounds who require significant daily exercise and have strong opinions about which route we take to optimize their sniffari experience. But the idea of structuring the back third of my life around the absence of meaningful work genuinely terrifies me in a way that no market downturn ever has.
2. The people who never got the memo. Here is just a partial list of people with more money than any reasonable person could spend in multiple lifetimes who are nonetheless completely, almost frantically engaged in continuing to build things:
Warren Buffett tap-dances to work at 95. Burton Malkiel writes more per day at 93 than most graduate students manage in a semester. Alex Cooper built Call Her Daddy from a microphone in an apartment into a media company worth hundreds of millions and has shown no interest whatsoever in stopping. Whitney Wolfe Herd founded Bumble at 25 after being pushed out of Tinder, took it public, and keeps building. Sara Blakely built Spanx from $5,000 in savings into a billion dollar company and immediately started her next thing. Charlie Munger was reading, writing, and arguing about ideas until the week he died at 99.
Note: I don’t highlight any of the above names because they have money; I highlight them because none of them seem to care about the money.
The pattern across all of them is not workaholism. It is not pathology. It is what Csikszentmihalyi spent his career trying to describe: flow. Being so absorbed in something genuinely meaningful and engaging that the question of whether to continue simply never arises.
3. The one question worth sitting with. Here’s your dose of philosophical reflection for the week: If there were no concept of retirement waiting for you at the end—no finish line, no date circled on the calendar, no penalty-free permission slip from your 401k—what would you change about how you’re living right now?
And the harder version: if you had to do exactly what you’re doing today for the rest of your life, what would you change?
Because if the answer to either question is “everything” or “a lot,” that is not a retirement problem. That is a today problem. And the retirement system has been very conveniently designed to let you defer that problem for decades, which is an extraordinary service to provide to an industry that profits from your continued participation in a system you’re not sure you believe in.
4. And in case that wasn’t enough, retirement asks you to wish away your life. This is the part that bothers me most and that I talk about online probably more than is socially acceptable.
The traditional retirement model is, at its core, a transaction. You trade the years when you are most capable, most energetic, most mentally sharp, and most physically able for a number in an account. And then you wait. You wait until you are older, possibly less healthy, certainly less flexible, and then you cash in the chips and figure out what you actually wanted in the first place.
David Foster Wallace said he hoped everyone could experience success early enough to realize it doesn’t solve the problems. Jim Carrey said the same thing with considerably better delivery. The real problems in our lives—the existential ones, the ones that keep you up at 3am—are not solved by a number. They are not solved by a date. They are solved by autonomy. By doing good work. By being around people you actually care about. And mostly (and I speak from pure lived experience here) by waking up each and every day to something worth doing well.
And the best part: none of that requires you to be 65. Or retired. None of that requires you to have $1 million in the bank. And none of it—not a single part of it—is improved by having spent forty years in a job you were counting down from rather than building toward.
5. I challenge you to find the work from which you don’t want to retire. I did not start this newsletter thinking about the day I’d get to stop writing it. I didn’t start making short form videos dreading the process of figuring out how to talk about money in sixty seconds. And I certainly didn’t start writing the book counting down the days until I could hand it in and never think about it again. That is not how this works. Take this newsletter as exhibit A: I write to you every week because the thinking it requires is the kind of thinking I want to be doing, and the dialogue it sparks among those of you reading it is the kind of dialogue worth having in this life.
But, and this is the key take-away, the day it stops feeling that way is the day I’ll change something, not the day I turn 65.
Here’s the only question that actually matters: if 65 weren’t coming to save you, what would you change about today? Answer that truthfully, and you’ll have more answers than most.
And if you want the full version, this week’s episode of Your Money Guide on the Side explores why the wealthiest people I know, literally and figuratively, have zero plans to retire. If you find the show useful, a review helps more than you’d think—it’s how new listeners find the show, and how I know the topics I find fascinating aren’t just fascinating to me and the hounds.
Listen on Apple | Listen on Spotify
Two Things I’m Currently Thinking About
1. One Year of Experience, Fifteen Times in a Row. Years ago, I was attending a coaching clinic put on by the Harvard squash coaches when someone in the room mentioned they had fifteen years of coaching experience, to which the Harvard coach responded—without missing a beat—“Do you have fifteen years of experience? Or one year of experience fifteen times in a row?”
It is the wisest thing I have ever heard someone say while wearing a Harvard fleece.
And I have been holding on to that line ever since.
Because most of us assume that simply by showing up—by accumulating years, by being present for the passage of time—we are somehow growing. That experience is something that accrues automatically, like interest. But the coach’s point is that many of us become so automated in our habits, so settled in what we already know, that we stopped actually learning somewhere around year three and have simply been repeating ourselves with increasing confidence ever since.
It changes how I think about hiring, about promoting, about the word “experience” on a resume. The question worth asking isn’t how long someone has been doing something. It’s what they actually absorbed from the doing of it in the first place.
2. The Remains of the Day and the Art of Actually Absorbing Experience.
Which brings me, as these things tend to do, to an English butler.
I can’t get enough of Kazuo Ishiguro’s writing. In The Remains of the Day, Stevens—our narrator, a butler whose lifelong goal is to achieve professionalism of the highest order—reflects on what separates the merely competent [butlers] from the truly great. The great butlers, he concludes, are those who have “acquired [greatness] over many years of self-training and the careful absorbing of experience.” Note: not the accumulating of experience. The absorbing of it.
That’s the word that I read that brought me back to the squash courts.
The Harvard squash coach and Ishiguro’s butler are making the same argument from opposite ends of the century. You can have thirty years in a room or thirty years of growth from a room. And only one of those is worth putting on a resume. Only one of those produces a legend.
What are you doing with your minutes? Are you absorbing them, or are you just letting them pass by and calling it experience?
And Before You Go…
This week’s newsletter is brought to you by LMNT.
Heading into summer, LMNT just dropped what is essentially their version of an Arnold Palmer—Lemonade Iced Tea—and I currently have a full pitcher of it in my fridge. A little caffeine alongside the salt and electrolytes is exactly what I want after a long walk with the hounds, or in the late afternoon when I’d otherwise be reaching for a second cup of coffee that I don’t actually need.
Now, here’s what makes it different: Most energy drinks use synthetic, isolated caffeine. LMNT uses full-spectrum organic black tea extract from Kericho, Kenya— 7,000 feet of elevation—so the caffeine comes with its naturally occurring L-theanine and polyphenols. The result is steadier energy, less spike, less crash, and only 50mg of caffeine per serving. Enough to matter. Not enough to regret.
I will also say this: my old cycling crew, people I hadn’t heard from in years, have all suddenly resumed contact with me with remarkable enthusiasm. And my sister—an elite marathoner who is extremely particular about what goes in her body—calls more than she used to. The pattern is consistent: every call starts with “hey, great to hear your voice” and ends with “so when can you send me more LMNT?” I have become, without intending to, a distributor, and I cannot decide if that’s a product endorsement or a personal confession.
So if you want to know what we’re all hyped up about, head to drinklmnt.com/tyler, become an LMNT Insider, and get four boxes for the price of three. That’s drinklmnt.com/tyler. And even though I am obsessed with the new flavor, this does nothing to diminish my feelings about mango chili and watermelon salt.
As always, hope this gives you something to think about throughout the week ahead.
—Tyler