Of Course Unlimited PTO is Awesome

Unlimited PTO sounds like a no-brainer. Let adults be adults. Don’t nickel-and-dime their time off. If the work’s getting done, who cares if someone takes a few days here or there?

And I agree. It’s the best PTO policy. Full stop.

But it’s also the easiest to screw up.

That’s why you see so many articles and LinkedIn posts railing against the “unlimited PTO trap.” Not because the policy is flawed, but because most companies are lazy. They roll it out with zero structure, then act surprised when it backfires.

Employees are understandably skeptical of anything that sounds too good to be true. And in most places, it is.

When your team is small and everyone is pulling in the same direction, unlimited PTO works beautifully with minimal effort. Goals are clear, communication is constant, and the culture is tight. You don’t need much structure because things are still small and simple. You just yell across the room (or the Slack channel), and everybody knows what’s going on.

At this stage, unlimited PTO isn’t just possible—it’s natural. You don’t need a PTO tracker. You don’t worry if someone’s taking “too much,” because there’s nowhere to hide and nothing to measure but the work itself. If it’s getting done, who cares if they’re in Mexico on a Tuesday?

But fast forward a couple years. You’ve grown. You’ve hired managers. Some people don’t see each other day to day. Goals are still there, but now they live in project management tools and OKR dashboards instead of hallway conversations.

Now things get fuzzy. One person takes two weeks off, no problem. Another does the same and gets side-eyed. Someone asks how many days they should take, and you say “however much you need,” but they hear, “Don’t push it.” Someone else hasn’t taken time off in eight months because they don’t want to look less committed. The trust that made unlimited PTO work in the beginning is still assumed, but no longer obvious.

Counterintuitively, unlimited PTO requires more management, not less.

Not because you’re counting days, but because you’re responsible for making sure people actually use the benefit as intended. That means setting cultural expectations, modeling the behavior, and tracking usage—not to limit it, but to encourage it.

It also means being willing to say the hard thing when someone is obviously taking advantage—or not taking time and burning out silently. Unlimited PTO is awesome, yes. But only if you’re mature enough to do the hard work of transparency, accountability, and honest conversations.

That’s why I rarely recommend it.

If your team is still small and aligned, enjoy the simplicity. But if you’re scaling and still pretending unlimited PTO runs on vibes, you’re not offering autonomy—you’re just avoiding structure.

Unlimited PTO is the best policy. But only if you do the work to support it.

And if you’re not willing to do that work? Just pick a number. People would rather have clarity than pretend-freedom.