Unlimited vacation sounds great on paper. But in some work cultures—especially high-growth tech environments—it’s a complete farce.

Let me be clear: I’m not here to trash my company. I’m grateful for the opportunity. I’ve learned a ton, and I wouldn't trade the experience. But that doesn't change the fact that I don’t feel safe taking time off. Not really.

Even on 16-hour days, there’s always more to do—and if anything slips through the cracks, it still comes back on me. The sheer volume of work makes it almost impossible to stay on top of everything. And because the company operates in a highly reactive mode, everything feels urgent all the time. Thrash becomes the norm.

If I’m even slightly unresponsive—say, offline for a night—people assume I’m not working. That I’m unreliable. The perception shifts instantly. And that perception shapes behavior. That’s terrifying.

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always on, never off

A colleague once told me he wasn’t planning to take any time off during his first year. Not because he didn’t want to—but because he didn’t think he could. The message is clear: time off puts you at risk. Even when people do take it, they still check Slack, still answer pings—because no one wants to be seen as disengaged. So what kind of “vacation” is that?

I’ve experienced it firsthand. I once got dinged for not responding quickly enough to a feature request that came in at 8 p.m. my time, on a weekend. I responded within 30 minutes to say I’d follow up the next day—reasonable, right? But within 12 hours, my manager had jumped in and taken over. He never told me where he posted his response. I followed up carefully, trying to do it right, only to be told I was duplicating work. And then I got flagged for being late.

There’s no winning. You’re expected to be deeply strategic, highly responsive, incredibly meticulous—and available at all hours. You’re supposed to juggle 20+ priorities, run internal tooling projects, lead customer onsites, and still deliver on every single priority.

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perfomative perks

Unlimited vacation with no minimum is not a benefit. It’s a loophole. It creates social pressure not to take time off, while giving companies the PR win of “generosity.” If you care about employee well-being, you should require a minimum of two weeks off. At least. Otherwise, the policy just rewards overwork and punishes rest.

What’s worse is that this dynamic disproportionately benefits those at the top. The people who’ve got large equity stakes have their time highly leveraged. Hell, if each hour I worked brought me notably closer to $100M, I'd be happy to grind.

But this isn’t just a leadership problem—it’s a structural one. In a system where value is measured by responsiveness and performative productivity, real long-term value gets deprioritized. You don’t build systems. You don’t go deep. You just react. They call it “bias toward action.” I call it distraction dressed up as discipline.

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unsustainable

This kind of culture—where being reachable becomes synonymous with being valuable—burns people out, fast. And unlimited vacation without boundaries just accelerates it.

If we want to build workplaces where people can actually thrive, it starts with designing against the race to the bottom. That means structural protections. That means cultural norms that encourage real rest. And yes, that probably means some outside governance—because left to optimize for profit, most companies won’t choose people.

Until then, we’ll keep grinding, smiling, and pretending this is normal.