Unlimited PTO: The Magic Trick That Isn't.

Now you see it. Now you don't.

Years ago, I went to a holiday party on one of those fabulous John Wayne boats in Newport Beach. The kind that cruises through Balboa’s Christmas lights while you sip something festive. Classic Southern California Christmas—warm, bright, and just a little magical.

But as both a guest and an HR person, my night was quickly hijacked. The company founder found me before I’d even finished my first drink and started asking about PTO. It was his holiday party, and yet, he couldn’t let go of that one question.

But before I could answer, Tenn and Peller, the local off-brand magician duo, kicked off their show. The famous “lady getting cut in half” trick began, and suddenly, I was struck by an HR alarm bell. I leaned in and whispered to the founder, “That’s a workers’ comp claim waiting to happen.”

He nodded, grabbed a drink, and dismissed me with a casual wave. It’s funny—people always ask for advice they don’t want to hear. They want someone to confirm their gut feeling, not listen

As I ordered my champagne cocktail, thoughts of Unlimited PTO danced in my head. My boss was pushing for it, employees were on board, and everyone seemed to think it was the next big thing. But something wasn’t sitting right with me. It felt too good to be true.

Unlimited PTO—sounds perfect, doesn’t it? No more tracking time, no more worrying about accruals—just PTO whenever you need it.

But here’s the problem: it’s a corporate magic trick, designed to look like freedom, but leaving employees tangled in uncertainty.

Why? Because, as the book Algorithms to Live By says, "The more options you give someone, the less likely they are to make a decision.” Unlimited PTO sounds like a dream, but it leaves employees with too many unknowns—will my time off be accepted? How do I know if I’ve taken too much?

Think about it. Most people won’t take the time off because they don’t want to seem like slackers. And without clear boundaries, that’s exactly what happens. The system isn’t well-defined, and uncertainty reigns.

And that’s when the trick is revealed. The illusion of PTO freedom collapses. The company wins because employees are too afraid to use it—and the company doesn’t have to pay for it. It's no longer a liability line item. It’s the kind of corporate sleight of hand that looks too good to be true—and usually is.

I contacted those low rent magicians, Tenn and Peller—and asked them to take a deep dive into whether Unlimited PTO is a corporate magic trick or a miracle. Spoiler alert: they weren’t impressed.

The more I thought about it, the more I realized: This isn’t about employee empowerment. It’s about company control. Unlimited PTO isn’t a golden ticket—it’s a sleight of hand that gives the illusion of freedom, but has a lot of strings attached.

You might be expecting a rabbit out of a hat, but here’s the real trick: the rabbit ain’t getting no PTO.