Avoiding the Cult of Retirement

for moderately privileged and highly idealistic dirtbags

The journey to true wealth begins with an idea that you’ve heard before, but it’s worth saying it once more, out loud, altogether now:

Don’t live for retirement.

Your body may fail you. Your investments may evaporate. You might get hit by a bus.

Money can always be earned. Time is nonrenewable. So live your life now, at least in part, rather than deferring it forever to the future.

There, you did it. You escaped the cult of retirement.

Or did you?

Are you grinding away in a high-paying job while spending very little, hoping to retire early? Then you are still in the cult. You’ve rethought consumption but not production.¹

Are you trying to build a business that will run itself—some kind of infinite money machine? Then you are still a cult member. You still imagine that money will solve your biggest problems.²

Are you burying your head in the sand, plodding away at a job you don’t particularly believe in, just trying to enjoy yourself on weekends and holidays? Then you, too, are a card-carrying cult member. You’ve just misplaced the card.

The cult of retirement will make you do silly and harmful things. After a hard day’s work, you will come home and wonder, “What exactly did I accomplish?” Tired and disillusioned, you will self-medicate with food, drink, drugs, and frivolous indulgences. The resulting hangovers will drain yet more of your precious time and money.

Even if you do succeed in making lots of money, even if you hit “your number,” there’s a decent chance you will look back on your efforts with a mixture of shame and self-doubt, filled with the gnawing awareness that you have traded away something vital.

Much like school, retirement is something in which almost everyone believes—and this alone should give you pause.

Even those who profess alternate visions of success tend to return to the idea that not working + lots of money = liberation. But if miserable lottery winners, listless retirees, and drifting trust funders have anything to teach us, it’s this: retirement is not the promised land.

What the obsession with retirement misses is this: more than money, more than ease, more than comfort, what people need is purpose.

Normal people find their purpose in shared time with loved ones: family dinners, brunch with friends, visits to grandma, school recitals, religious communities, and vacations with their spouse.

Normal people take normal jobs in order to generate the money necessary to spend time with loved ones. When they retire, they hope to spend even more time with loved ones. Work also provides an identity: a way to neatly describe their role in the world.

This is all well and good—for normal people.

If you are reading this, I’m assuming you’re not such a person. You are either a dirtbag, dirtbag-adjacent, or dirtbag-curious. You are a non-normal individual who finds deep purpose in intense, physical experiences like climbing, skiing, surfing, trail running, long-distance hiking, mountain biking, cycle touring, dancing, acrobatics, or long-term travel. You also find purpose in the communities of like-minded weirdos who coalesce around these activities. You find your identity here, too. And hopefully you still make time for grandma.

But dirtbags and normies curiously share a common belief: the idea that work is to be avoided. One believes that work is a means to an end for having a normal social life. The other believes that work is a means to an end for “getting after it.” Both seek their purpose primarily outside of work.

I admire dirtbags. They’ve taken a giant leap away from the cult of retirement. They don’t wait for weekends, employer-approved vacations, or some mythical future to live their purpose. Dirtbags are rich in time, experience, and connections. They don’t have much money, but at least they don’t struggle with full-time jobs sapping energy.

If dirtbags didn’t resent the part-time or seasonal jobs to which they inevitably returned, then their lives would be even more amazing. If they could have purpose all the time, how good could life become?

The classic deal is this: Try to earn lots of money, with little regard for purpose or time. If you succeed, then you’ll enjoy lots of time and purpose upon retirement.

The risks of the classic deal include: Not actually saving enough to retire (due to the money you spend self-medicating) and not enjoying your retirement (due to tiredness of body and spirit).

The dirtbag rich deal is this: Try to have it all now—deep purpose, time wealth, and sufficient money—at the risk of forsaking a security net that others consider essential.

If you fail, you may end up relying on family, the government, or a romantic partner. You may live in a trailer, work at a big box store, and face daily indignations that more diligent adults (those who “sucked it up” and “did what they must”) consider humiliating.

The risks are real. The dirtbag rich deal is not for everyone. It’s best suited, in fact, for one particular group: the moderately privileged and highly idealistic.

“Moderately privileged” means that you, like me, were born into the progress party. It means that you enjoy multiple advantages that let you lead an empowered, self-directed life: decent health, a stable upbringing, some form of education, and membership in a society that does not powerfully discriminate against you. (For my social-justice-oriented readers: this may be a larger group than you imagine.)

“Highly idealistic” means that you, like me, are not content to merely reproduce your privilege. It means that you want to redistribute your unearned gifts by living a different kind of life, by tinkering with new notions of “progress,” and by experimenting with new versions of “freedom.” Instead of dwelling in ease and comfort, you will take the chance to make art, innovate with business, build movements, and bridge cultures. Rather than seeking riches and retirement, you’ll attempt make a unique, purposeful contribution to Team Human—today and tomorrow, all the way to your dying days, while enjoying yourself along the way.

The most important question isn’t: Can everyone in the world become dirtbag rich today?

But rather: Will you do more good in the world—both for yourself and others—by attempting to live like this?

And: If your life ended unexpectedly tomorrow, would you regret trying?

Green River (Utah), 2019

[This is an excerpt from the Dirtbag Rich manuscript-in-progress. It probably won’t end up in the book.]

1. Listen to my critique of FIRE (financial independence, retire early) on TikTok.

2. Yes, I’m referencing The 4-Hour Work Week. I have more thoughts.