Jack Flintoft

VC @ Dorm Room Fund, undergrad @ UChicago

Humans as a species have a remarkable ability to conjure up new jobs almost out of thin air.

Eighty years ago, “child care worker” as a formal job title basically didn’t exist. Before World War II, childcare was handled mostly by family, neighbors, or older siblings. Hell, the idea of paying a professional to watch your kids was almost unheard of.

After WWII hit, millions of men went to war, millions of women entered factories, and suddenly someone had to look after the children.

So in 1943, the U.S. government passed the Lanham Act, funding thousands of federally backed childcare centers to keep the workforce running. By 1944, over 3,000 centers were caring for 130,000 kids. Overnight, childcare became a structured profession — and today employs millions.

Jobs that once seemed unimaginable become normal. They always do.

And it’s not just childcare workers. This same pattern plays out across industries. Forty years ago, sustainability consultants and ESG investors would have been laughed out of the room. Twenty years ago, the idea that millions would earn a living as Twitch streamers or Instagram micro‑influencers would’ve sounded absurd.

We as a species keep doing this. Every time society recalibrates, we create new jobs and entire industries seemingly from nothing.

Famously, the ATM was supposed to kill the bank teller. Industryy watchers predicted that automation would make the role obsolete. Instead, they just automated the most repetitive part of the job — depositing and withdrawing cash. Tellers shifted to more customer-facing work. Banks actually opened more branches, and hired more people.

And now, with AI, we’re hearing the same fear again — that this time, work might finally disappear (and rightly so — it replaces labour, and that’s uncomfortable).

But if history is any guide, (a) it might actually bring us closer to the parts of work that matter, and (b) we’ll just keep inventing new forms of it.

And like the ATM example, many of those new forms of work end up feeling more human and less alienating than what came before (think: YouTube creators, Peloton instructors, Fiverr freelancers). Like Smith’s famous example, historically the pin factory worker spent his entire day performing just one of the eighteen tasks needed to make a pin (imagine the isolation!). He might never even see a finished product. You could spend a decade perfecting the art of cutting pin wire and still never once feel the satisfaction of holding the thing you helped create.

Compare that to someone teaching spin classes on Peloton. Their labour isn’t split into eighteen invisible steps. They plan the workout, deliver it live, interact with viewers in real time, and see direct feedback from a community of followers. Fiverr freelancers are similar — they write / design / code / photograph something from start to finish, send it off, and often get a thank you note or a five star review.

These jobs exist because of tech — but they also feel more human because of it.

Yes, we’ve always been good at physical work (or process-oriented work), but we’re even better at the stuff that’s innately human — connection / creativity / care.

That’s why the conversation around AI feels different. It’s not just another Industrial Revolution replacing physical labour — AI reaches into intellectual work too (writing, thinking, reasoning, etc.).

But again, history seems to give us a pattern: tech changes what we do, and we respond humanly by finding new things to do, or ways to do it.

Part of this thinking comes from Marx. He’s often misunderstood as purely “the dude who talks about communism,” but really, if you read even the first volume of Capital, Marx never mentions “communism” or “communist” once (in 1000+ pages).. He was (at heart) a critic of capitalism — and more of a historical economist than anything.

He was fascinated by how capitalism constantly reinvents the nature of work (something my Marx professor last year hounded into me). Marx wrote about its restless need to generate surplus — how every gain in efficiency births new forms of labour. For even if, in theory, we could all live comfortably working two hours a day, we don’t. 

“Capital is dead labour, which, vampire-like, lives only by sucking living labour, and lives the more, the more labour it sucks.” — Marx, Capital I, Ch. 10

Even when machines could liberate us, they didn’t (they needed to keep sucking the “living labour” of humans). Indeed, we just found new ways to keep working — and keep feeding the machine.

But maybe it’s not just the machine. Maybe it’s us.

Thousands of years ago, Hesiod wrote Works and Days, a poem trying to show that work isn’t disgraceful. Instead, idleness is. He tells his brothher that the gods deliberately made life hard so humans would keep moving.

“For the gods keep hidden from men the means of life. Else you would easily do work enough in a day to supply you for a full year even without working; soon would you put away your rudder over the smoke.” — Hesiod, Works and Days

In other words, if life ever became too easy, we’d hang up our tools and stop.

And yet, thousands of years later, we haven’t. Even as work has gotten easier, it hasn’t disappeared. It just keeps changing shape — over and over again, as both Hesiod and Marx seemed to know it would.

And here we are again. AI will replace some jobs — it already has. But if history is any guide, it’ll also reshape what we value, what we pay for, and what we aspire to become.

We as humans will invent new jobs, new tools, new ways to feel useful — just like we always have.

Twenty years ago, no one predicted that being a YouTuber would be a dream job for high schoolers (alas, I tried and failed). No one imagined gig workers making a living on Upwork or Uber. None of this existed in the cultural zeitgeist — until suddenly, it did.

So maybe the future of work isn’t something that happens to us, but rather something we keep making up as we go …

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