The Safe Path Is Dissolving

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A lot has changed since I last wrote here. After twelve years at ThoughtSpot, most of my time now goes into a new company I started called AmpUp—we help sales teams close the gap between their best reps and everyone else. And somewhere along the way, I learned something about myself that I wish I’d understood decades earlier.

This post is about that lesson. It started as advice to a friend’s daughter, but it turned into something more personal.

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A friend asked me for advice about her daughter, a second-year college student studying electronics. The daughter is anxious about the future—about what jobs will exist, what skills will matter, whether she’s on the right path. I found myself writing a longer response than I expected, because I’ve been thinking about this a lot.

Here’s what I’ve come to believe: For the better part of a century, we’ve lived inside a particular bargain. Go to school, go to college, get good grades, follow directions, and society will give you a safe place. A job. A trajectory. A life you can more or less predict.

That bargain is dissolving.

The Theater-to-Netflix Problem

Before mass media—before radio and television—if you wanted entertainment, you went to the local theater. That was the best anyone could do. Then technology made it possible to replicate human performance at near-zero marginal cost. Suddenly, for a few dollars, you could watch a billion-dollar production in your living room. Entertainment became a winner-take-all market almost overnight.

This is now happening to expertise. Engineering, medicine, law, financial advising, tax preparation—any domain where the core work involves applying established knowledge to routine problems is becoming compressible. Not disappearing. Compressing. A smaller number of people, augmented by AI, can do what used to require large teams.

If LLMs make it so that any routine task—anything that doesn’t require inventing new things—becomes easily automatable, then the remaining work shifts toward invention. Not just fundamental research, but entrepreneurial work: making bets, searching for niches, trying and failing and trying again until you land on something valuable. Having a sharp feedback loop so you fail fast and correct course. Being genuinely good at listening to people, asking real questions, synthesizing patterns no one has seen before.

The Comedian’s Career

A comedian can’t hide behind credentials. They walk on stage and either the room laughs or it doesn’t. They bomb, they adjust, they try again. They earn their place through repeated acts of vulnerability—not once, but every single night.

That used to be the exception. Artists and entrepreneurs lived that way while everyone else had the safety of defined roles and predictable advancement. Now that safety is dissolving. Your engineering career is becoming a comedy career whether you signed up for it or not.

The question isn’t whether you’ll face that exposure. It’s whether you’ll lean into it or spend years resisting the inevitable.

What I Got Wrong

I’m not writing this from some perch of having figured it out.

I spent years giving myself permission to stay comfortable. First there was the green card—I couldn’t take risks while my immigration status was uncertain. Then I became “the technical co-founder” at ThoughtSpot, which meant I had a lane. I stayed in that lane for twelve years, even when I sensed I had more to contribute in other domains—strategy, positioning, customer intuition. I told myself I was being responsible, playing to my strengths. Really, I was avoiding the harder work of developing judgment in areas where I wasn’t already good.

When I finally had the freedom to build something new, I tried to build everything—an agentic AI platform for anything and anyone. It felt expansive and safe at the same time. Safe because I never had to commit. I could stay in the realm of possibility, keep all doors open, avoid the exposure of saying “this is my bet, judge me on it.”

AmpUp exists because I finally made myself choose. Closing the gap between your best sales reps and everyone else. Not a platform for everyone. Not a solution for everything. A narrow lane where I could be wrong in a specific, measurable way.

That choosing was harder than any technical problem I’ve solved.

So What Does This Mean for a 20-Year-Old?

You don’t have to start a company. But you have to get specific about the future you want—even when you don’t have enough information to be certain. Especially then.

The method is: imagine the transformed version of a field you care about, then work backward to what skills and relationships matter today.

Healthcare: In ten years, routine diagnosis and treatment may be largely automated. The premium shifts to rare disease combinations, cases that don’t fit patterns, interpreting what’s happening with patients who fall between categories. And the irreducible core: being present with people in their most vulnerable moments. Machines can diagnose; they can’t hold a hand. If this interests you, maybe you study less anatomy and more pattern recognition, systems thinking, communication. You find the 50 doctors already working on the frontier of this and figure out how to be useful to them.

Finance: Basic analysis gets fully automated. The edge moves to judgment calls requiring synthesis of non-obvious signals—geopolitical intuition, founder psychology, cultural shifts that don’t show up in data yet. A student interested in this might study behavioral economics and history rather than just finance, seek out contrarian investors, and start writing publicly about patterns they notice. Building a track record of thinking, not just credentials.

Law: Contract work and legal research get commoditized. What remains is high-stakes negotiation, novel regulatory territory (AI governance, bioethics, space law), and situations where human judgment and trust are essential. A student might focus less on case law and more on understanding how new technologies create legal vacuums, then find the handful of lawyers actually working on frontier issues and offer to help them think.

Engineering: Implementation becomes cheaper. The premium shifts to problem selection—figuring out what to build, not just how. This means deeply understanding a domain rather than accumulating technical skills alone. The kid who spends a summer working at a trucking company and understanding their actual pain points may be better positioned than one who does another coding bootcamp.

Creative fields: Production quality gets democratized. Distinction comes from having a genuine point of view, building direct relationships with an audience, operating at the intersection of fields. The question isn’t “how do I get hired by a studio” but “what do I have to say that no one else is saying, and who specifically cares?”

The common thread: In every case, the move is from “acquire credentials in established category” to “develop a thesis about where value is moving, find the people actually working on that frontier, and make yourself useful to them.”

It’s less about entrepreneurship as starting-a-company and more about entrepreneurial thinking—treating your career like a search problem rather than an optimization problem.

More Alive, More Scary

I know this sounds hard. It is hard. The safe path was easier—you just had to follow the script. But here’s the thing: the safe path was also, in a way, a trap. A lot of people got stuck in systems that never pushed them to discover what they were actually capable of. They continued as cogs. There was never enough internal motivation or external force to try something unsafe.

The world that’s emerging will be harder. But it might also push more people toward greatness—because there’s no longer a comfortable middle to hide in.

The definition of work is going to shift—maybe as dramatically as it did when we went from breaking our backs on farms to typing on glass screens in air-conditioned rooms. To a farmer in 1924, what we call “work” today would look like sorcery. Or leisure.

But here’s what won’t change: we won’t just sit around in bliss. The hedonic treadmill guarantees new status games, new struggles. The question is whether you’re playing games you chose or games that were handed to you.

Make Your Choices Right

A mentor once told me: “We don’t make right choices. We make our choices right.”

I wish I’d understood that earlier. I spent years looking for the safe bet, the optimal path, the choice I couldn’t get wrong. That search was the trap. The real work was always on the other side of choosing—in the commitment, the iteration, the willingness to make whatever I chose into something worth having chosen.

The fear isn’t just “what if I don’t choose.” It’s “what if I choose wrong.” But that’s exactly what his words answer: there is no right choice waiting to be discovered. There’s only the choice you make and what you do with it.

I don’t have all the answers. This is a hypothesis. But it’s the one I’m betting on—for AmpUp, and for what I’d tell any young person navigating this moment.

Pick a lane. Make a bet. Then make that bet right.

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If this resonated, I’d love to hear from you—especially if you’re a parent navigating this with your kids, or a young person figuring it out yourself. And if you’re curious about what I’m building at AmpUp, you can find us at ampup.ai.