Lonely at the Top: On the Myth and Misery of Being CEO

To outsiders, the CEO title glows with a sort of untouchable glamour. Power. Prestige. The final say. To founders, it’s usually shorthand for: chief stress receptacle. It may look like the top of the pyramid, but it often feels like a bunker. You are the last line of defense between order and collapse, armed only with a PowerPoint deck, a cap table, and the ability to pretend you’re fine on five hours of sleep.

Especially in small companies, the CEO isn’t just “the boss.” You’re head of fundraising, HR, legal, procurement, and crisis management. You are both strategist and fire marshal. If the salaries aren’t paid, that’s on you. If a regulatory filing is late, that’s on you. If a former college buddy you hired turns into a free-rider, you not only have to fire him—you also have to figure out how to do it without a lawsuit or a LinkedIn post about “toxic leadership.”

People think leadership is about vision. It is, in the same way that flying is about scenery. What it really is, is weight. The knowledge that your decisions affect not just outcomes, but livelihoods. That every failed quarter, every delay, every misfire—whether caused by you or not—will ultimately be hung around your neck like a burnt garland.

As the saying goes, “the buck stops here.” It was popularized by President Truman, who kept a sign with that phrase on his desk. It was meant to signal accountability. Today, it's more like an epitaph for executive sanity. Because when things go wrong, the buck doesn’t just stop with the CEO. It sets up camp, audits your calendar, and sends its regards to your stress hormones.

Ben Horowitz captured this bleak reality in his excellent book, The Hard Thing About Hard Things. One passage in particular sticks: “By far the most difficult skill I learned as a CEO was the ability to manage my own psychology.” It’s not raising the money or setting strategy that breaks most founders. It’s the internal monologue. The sleeplessness. The slow corrosion of confidence that comes from delivering bad news week after week while projecting optimism to everyone else.

Who do you turn to? Your investors want reassurance. Your team wants clarity. Your co-founder may be just as fried as you are. Therapy, if you’re lucky. Whiskey, if not. Many CEOs, unfortunately, choose chemical shortcuts. There’s an entire body of research (and Silicon Valley lore) on substance dependency among executives. And yes, if you're Elon Musk, perhaps the ketamine works. But that’s a different story, and a different tax bracket.

There’s a peculiar loneliness in leadership because it’s asymmetrical. Everyone sees your decisions, but not your doubts. They critique the outputs, not the constraints. And inevitably, some well-meaning soul will say, “If I were CEO, I’d do it differently.” Yes, well—you’re not. There’s a reason most people opt out of the top seat. The fantasy is more pleasant than the responsibility.

Even after years, it never gets easier. You grow thicker skin, better frameworks, maybe even a more polished slide deck. But the fundamental shape of the burden remains unchanged: you are responsible. For the people, the plan, the pivot. For holding it all together even as things fall apart. It is not glamorous. It is not fair. It is simply part of the job.

So next time someone tells you they dream of being CEO, by all means encourage them. But also hand them a copy of The Hard Thing About Hard Things, a bottle of aspirin, and your therapist’s number. And remind them: it’s lonely at the top. But at least the view is clear.