"Unlimited PTO" or "Vacation Freedom" or whatever cool term some people person wants to stick on it... it's really only as good as the company culture, boss and

"Unlimited PTO" or "Vacation Freedom" or whatever cool term some people person wants to stick on it... it's really only as good as the company culture, boss and you make it. It's truly a combo of all three and people often forget that last one. I've worked in several companies now that offer unlimited vacation. At first it was very strange to me and to be honest I didn't really utilize it properly at first. As I got older and wiser, I've been better at using it ... and also been at companies that were more vacation friendly. If your boss is all for you taking the time off that you need, because your boss treats you like a fully grown adult capable of doing your work... you're gonna have a great time. If your company culture doesn't look at you like you have 3 heads for taking a half day off, you're probably good to go. If you remember that in order to enjoy the "benefit" of those vacations is to actually take the time off... then happiness is. Most of the time when talking about unlimited PTO vs regular, people hammer on the point of "unlimited PTO = no money when you leave". For those people who want to work at a company for 366 days straight, get their 1yr cliff options, quit, take a month long vacation, get a new job...repeat. Then for them, they are totally correct, the pay out is good. However if you get smart about actually USING your vacation periodically, then who cares about the payout?