Unlimited PTO

Back when I was contracting, I had zero paid vacation. If I didn't work, I didn't earn money, so I tended to take very little vacation time. I would go on vacations, but I would always spend at least a few hours most days getting billable work done.

With that in mind, I'd have expected to be pleased with any paid time off. And, of course, I am. I can see, at a glance, exactly how much vacation time I've earned. But, watching my available time off accrue (slowly) feels stifling. It is way more time than I'd ever take off as a contractor, but now I'm actually limited by it. And somehow that's worse.

I understand that Unlimited PTO policies tend to reduce the actual amount of time off that employees take. That fits with my experience as a contractor. If I know I can take time off if I want to, I'm less concerned with doing so. When my employer tells me that I have a very specific limit, then I'm naturally going to feel trapped by it.

Human psychology is weird.