"A human being should be able to change a diaper, plan an invasion, butcher a hog, conn a ship, design a building, write a sonnet, balance accounts, build a wall, set a bone, comfort the dying, take orders, give orders, cooperate, act alone, solve equations, analyze a new problem, pitch manure, program a computer, cook a tasty meal, fight efficiently, die gallantly.
Specialization is for insects." — Robert A. Heinlein
I learned the basics of programming in high school by breaking the Wang 286 my father brought home from work in 1987. It was the first computer in Lobos, the small town where we lived. It never occurred to me I could make a living out of it.
At fourteen, I started playing piano. I played in a folklore group that, after a few years of medals of every color, won the province-wide youth games. The prize was a trip to Europe (apparently there was still something left in the province's coffers in the '90s). Along the way we ended up playing for Pope John Paul II. I never played again after that.
At seventeen I moved to Buenos Aires to study economics with three guys from Lobos I barely knew: my father had talked to every parent he came across with kids the same age, so we could split the rent.
I landed my first job doing customer support and implementing ERP software, until I hit the limits of customization and started digging into how those ERPs were built. I ended up switching careers to study information systems.
By twenty-five I had tried multiple roles and industries. I led tech projects across LatAm, and out of necessity I'd learned enough of each role around me (engineers, sysadmins, business analysts, project managers) to keep things running when someone took vacation, quit, or got hit by the proverbial bus.
I'd also learned to change the diapers of my newborn daughter.
Two kinds of careers
I love getting obsessed with topics. Always have. I start pulling the thread more and more until most of my day goes into it. At some point I let go (something unconscious about the marginal cost of getting 1% better, I guess). It stays there, in the background, until years later it resurfaces because it combines well with something else, or helps me solve something even harder.
But in professional settings, that obsessive behavior was never seen as a virtue: corporations need little boxes with titles, roles, sets of expectations. Managers aren't supposed to code. Tech leads have no business talking to sales. Nobody likes the guy who skips around the org chart. Yet ignoring it is the only way to see the bigger picture.
So I left the corporate world (mostly) and started working at startups, where being a generalist is an advantage rather than a character flaw. I can jump from tech strategy to product definition, from hiring to architecture, from code review to customer calls, whatever the moment demands.
But this kind of career is rarely up and to the right: mine sometimes goes sideways, sometimes straight down. I take lower-paying jobs if they buy me exposure to things I don't understand yet. Every jump expands the surface of things I know I don't know: FinTech, InsurTech, AgTech, BioTech.
Had I followed a specialist's path, things would have been obviously different. Specialization digs deep into a single area. And, in a stable world, that expertise pays: reliable returns, a career ladder, a raise every year.
But the part that goes unnoticed is that it's a concave bet. When your entire edge is knowing one domain better than anyone else, any disruption to that domain is an existential threat. Imagine dedicating your whole life to driving a horse-drawn carriage, or operating an elevator.
A generalist career is the opposite bet. It's convex. You're wrong a lot: some jumps lead nowhere, you take pay cuts to change jobs, you abandon skills and start over more times than you can count.
A few years back I walked away from a well-paying US contract to bet on a local project. But Argentina being Argentina, the political winds shifted and the opportunity deflated before I could capitalize on it. I was back where I started.
It didn't pay, at least not in cash. But that's the shape of a convex bet: you can only lose what you put in, while what you carry out of it can pay off in directions you never imagine.
Look, this isn't an argument for knowing a little about everything. Being shallow has very little upside. What I'm describing is closer to what Kent Beck calls a "paint drip": you move the brush across the canvas following your curiosity, and depth forms wherever you stay long enough. The goal isn't breadth for its own sake. It's being genuinely good at several things, so the combinations become your edge.
Who would you bet an increasingly exponential, AI-dominated world will reward more: the specialist or the "expert generalist"?
Daniel Rabinovich, COO and former CTO of Mercado Libre, says nothing is riskier today than being a super-specialist. On top of managing 140,000 people, he's a magician, a chess player, a speedcuber, and a musician.
There's even a pre-AI version of this debate between Malcolm Gladwell, who popularized the idea that mastery requires 10,000 hours of practice in one domain, and David Epstein, author of Range. Gladwell eventually conceded that his 10,000 hours rule works in what he calls "kind" environments. Settings where the rules are clear, feedback is immediate, and patterns repeat. Chess. Surgery. Tennis.
If you're building a compiler, designing an airplane, or operating on a brain, you don't want the renaissance man. You want the person who has done this one thing ten thousand times.
But most of life isn't kind. It's what Epstein calls a "wicked" environment. Rules are unclear, feedback is delayed or misleading, and you can do the right thing and still get the wrong outcome. Business is wicked. Strategy is wicked. Innovation is wicked.
And a kind environment (clear rules, clean feedback, repeating patterns) is the easiest thing to teach a machine. The specialist's ground is the most exposed.
The least exposed edge
The specialist is optimized for a world that doesn't change much. The expert generalist, on the other hand, is antifragile. To borrow Nassim Taleb's term: they gain from disorder, because every disruption is another opportunity to learn a new domain and connect ideas.
This Harvard study posted 166 R&D problems that specialist teams couldn't crack. About a third were solved by outsiders, and the further the solver's field was from the problem's domain, the more likely they got it. Chemists solving biology problems. Physicists solving chemistry problems.
My years implementing ERPs for Argentine SMBs gave me a good sense of how businesses actually run beneath the org chart. A decade later, that knowledge lets me diagnose problems by seeing past the purely technical. And my economics background helps me frame those decisions in a way non-technical stakeholders can understand.
Knowing a lot about one thing is getting cheaper. Knowing a little about many things, too. What's less likely to get cheaper is picking which problem to solve, sensing when an answer doesn't add up, and connecting patterns across fields. Call it judgment across range.
But no one searches for a generalist
This path has its downsides too. No one types "generalist" into a search box: not recruiters, not clients, not the algorithm deciding who gets found. The market needs a label to file us under, and if we refuse to pick one, we stay invisible.
But you can specialize the doorway and generalize the work.
My own positioning isn't "generalist." It's narrow on purpose. One role, one stage, one market. Defined enough that the right founder knows at a glance I'm built for them. That's the door. But the work behind it is pure range: product strategy one hour, architecture the next, a hiring plan after lunch.
Picking a door specializes your positioning, not your learning. The paint drip keeps spreading underneath. The door can be as narrow as we want, but what passes through it doesn't have to be.
Maybe it's time to change a diaper, plan an invasion, write a sonnet, program a computer, and cook a tasty meal.
After all, that's what humans are for.
Specialization is for insects.
