The Comfort Trap

Imagination is more important than knowledge.

Why Smart People Stay Too Long

I was at a friend’s company recently when they held a ten-year anniversary celebration for one of their engineers. It was a nice event. There was cake. The CEO gave a speech about loyalty and impact. Everyone seemed genuinely happy.

But I kept thinking about opportunity cost.

Not the engineer’s opportunity cost—that was obvious. They’d traded their peak building years for a salary and some equity that would never fundamentally change their life. I was thinking about society’s opportunity cost. Here was someone clearly capable of creating something new, instead optimizing someone else’s creation.

This pattern is everywhere in tech now, and it’s getting worse.

The Mathematics of Building

Let’s start with the numbers, because they’re clarifying.

Building a significant company takes 5-10 years. This isn’t a rule exactly, but it’s rare enough to see exceptions that we can treat it as one. Facebook, Google, Amazon—they all took roughly a decade to become what we’d recognize as successful. Even the companies that seem like overnight successes usually aren’t. Airbnb was founded in 2008 and didn’t become profitable until 2017.

Failing, by contrast, is fast. You usually know within 1-3 years if something isn’t working. The market tells you, clearly and repeatedly, when you’re building something nobody wants.

Given a productive career of about 40 years, this means you get perhaps 6-8 real attempts at building something significant. Not side projects or lifestyle businesses, but real attempts at building something that could matter.

Most people never use even one of these attempts.

The Premium Employee Phenomenon

What do they do instead? They become what I’ve started thinking of as “premium employees”—people with founder-level abilities who’ve chosen employee-level ownership.

These aren’t typical corporate workers. They’re exceptional. They ship products that millions use. They solve hard technical problems. They understand customers, markets, and business models. In many cases, they’re more capable than the founders they work for.

But they’ve made a curious trade. They’ve exchanged the possibility of building something significant for the certainty of building someone else’s thing.

The economics of this trade have gotten worse over time, but in a way that’s hard to see year-to-year. In 1990, a senior engineer at Microsoft could reasonably expect to retire wealthy from employee stock options. By 2000, you needed to be in the first 100 employees at Google. By 2010, the first 50 at Facebook. Today? Unless you’re at an AI company pre-product-market fit, employee equity is mostly a retention tool, not a wealth-creation mechanism.

Yet the comfort has increased proportionally. Tech companies have gotten very good at making employment feel like entrepreneurship. You “own” products. You make “bets.” You think about “strategy.” But you don’t own anything, your bets are with someone else’s chips, and your strategy is constrained by someone else’s vision.

The Cognitive Dissonance

The interesting psychological phenomenon is that these premium employees know this. They’re too smart not to.

They have startup ideas. Often good ones. They see problems in their companies that could be standalone businesses. They know early employees at successful startups who are now wealthy. They read the same essays about building companies that you’re reading now.

But they stay.

They stay through multiple re-orgs that reset their trajectory. They stay through bad strategic decisions they predicted would fail. They stay through the departure of colleagues who go on to build successful companies.

Why?

The Comfort Gradient

The traditional explanation is risk aversion, but that’s not quite right. These people deal with risk constantly. They join projects that might get cancelled. They work for executives who might leave. They build on platforms that might change. They’re comfortable with uncertainty—as long as someone else owns it.

What they’re actually optimizing for is something subtler: the ability to be selective about which problems they solve.

When you work at a successful company, you can choose to work on interesting technical problems without worrying about distribution. You can focus on architecture without thinking about sales. You can optimize algorithms without negotiating contracts. The company is a platform that lets you do the fun parts of building while someone else handles the parts you’d rather not think about.

Starting a company means you have to do everything, especially the things you’re bad at or don’t enjoy. That’s the real fear—not failure, but discomfort. Not bankruptcy, but boredom. Not running out of money, but running out of enthusiasm for the parts of building a business that aren’t intellectually stimulating.

The Local Maximum

This creates a local maximum problem. Every year, the premium employee gets better at being an employee. They learn the promotion system. They build internal credibility. They understand the political dynamics. They get very good at navigating their specific context.

But none of these skills transfer to building something new. In fact, they often make it harder. The muscle memory of having resources makes it hard to be scrappy. The habit of consensus-building makes it hard to make fast decisions. The comfort of a salary makes the volatility of founder life feel unnecessarily harsh.

So they stay another year. And another. And eventually, they’ve been there a decade.

The Real Cost

The individual cost is obvious: they never build anything of their own. They retire with a nice house and a 401k or ISA but no lasting creation. They optimized for comfort and got it.

But the societal cost is larger and less visible. Every premium employee who doesn’t start a company is a company that doesn’t exist. It’s jobs that aren’t created, innovations that don’t happen, and problems that don’t get solved.

This might sound melodramatic, but consider: if even 10% of the premium employees at big tech companies started their own companies, we’d have thousands more startups. Most would fail, but some wouldn’t. The ones that succeeded would create more opportunities for the next generation to either join or compete with.

Instead, we have a generation of the most capable people in tech spending their careers optimizing metrics for companies that are already successful.

The Window

The crucial insight is that the window for starting something doesn’t stay open forever. Not because of age—plenty of successful founders start in their 40s or 50s. But because of identity.

After a decade as a senior employee, your identity becomes intertwined with your role. You’re not someone who happens to work at Google; you’re a Googler. You’re not someone who solves problems; you’re a Staff Engineer. The longer you stay, the harder it becomes to imagine yourself as anything else.

This is why the ten-year anniversary celebration I mentioned at the start felt so poignant. It wasn’t just celebrating a decade of employment. It was, in a way, celebrating the closing of a door. The engineer being celebrated was talented enough to build something significant. But after ten years, they almost certainly won’t.

The Question

So the question becomes: if you’re a premium employee reading this, what should you do?

The answer isn’t necessarily to quit tomorrow and start a company. That’s the kind of dramatic gesture that makes for good stories but bad decisions.

The answer is to be honest about what you’re optimizing for. If you’re optimizing for comfort, stability, and the ability to work on interesting technical problems without business responsibility, then stay. There’s nothing wrong with that choice. Someone needs to build the infrastructure that everyone else builds on.

But if you’re staying because you’re telling yourself you’re “not ready” or you’re “learning” or you’re “waiting for the right idea,” then you’re lying to yourself. You’re ready. You’ve learned enough. And the right idea is the one you’ve been thinking about for the past three years but haven’t acted on.

The tragedy isn’t that smart people work for others. It’s that they convince themselves they’re entrepreneurs in waiting when they’re actually employees by choice. The sooner you admit which one you are, the sooner you can either make peace with it or change it.

The clock, as they say, is ticking. But it’s not ticking toward some deadline where it becomes impossible to start. It’s ticking toward the point where you’ll no longer want to.

And that point comes sooner than most people think.