It never works out that way. I worked at a company with very limited fixed vacation. We got 10 days a year, but 4 were required to be taken between Christmas an

It never works out that way. I worked at a company with very limited fixed vacation. We got 10 days a year, but 4 were required to be taken between Christmas and New Years, which really meant you had 6 days to use at your discretion. There were ways to squeeze some extra, but at best you got 2 weeks. My wife was in a similar boat and switched to a VC backed startup with 'unlimited vacation'. I remember high fiving about it and thinking THIS IS AMAZING. Fast forward one year, she had taken 3 days off in the entire year. The next year when she actually went to take a vacation, her boss asked her "oh didn't you go to that island last year?". The fact that she took almost nil vacation the year before was not remembered. You can imagine she left very soon there after. We have grown up a lot since then, and would never get suckered into that situation now. But it happens. When your boss never lets you take vacation, 'unlimited' vacation is 'no' vacation.