I've just accepted a position at a YC startup with "unlimited vacation days". The founders seemed genuine when they said that as long as your work is getting done, it wasn't a problem.

I still agree that it causes ambiguity about how much time off is "too much".

I was very wary of the "unlimited vacation policy" at my new company and asked about it during interviews. Most interviewers agreed that it could cause people to not feel free to take vacation, but that the company really meant it and there wouldn't be negative consequences if you took vacation.

Fast forward to 6 months into the job and I've taken days off for long wedding weekends and have some more extended travel planned in the future.

I agree that "unlimited vacation days" can be a red flag, but it really just means to be more curious and thoughtful about the culture during the interview process and find out what it really means.

I recently joined a NYC company with "unlimited vacation days", and they do actually mean it. I mentioned this very trend when I was interviewing. They responded by saying they expect me to take AT LEAST three weeks of vacation a year.

Now, some of my coworkers are workaholics and won't take that much. But I have had success in just saying "I want to take these weeks off."

Apologies for the side-track, but I once had a boss offer to give me "unlimited vacation days" as a colloquialism for firing me after complaining when he took away some vacation days company-wide. Good to see the phrase has evolved.