You need to ask yourself: Why does the company do this? Why does the company not grant everybody 50 vacation days by default and encourage employees to work mor

You need to ask yourself: Why does the company do this? Why does the company not grant everybody 50 vacation days by default and encourage employees to work more by paying out small bonuses (like $500) for not taking more than 50% of their vacation days? It's because they want the employees to not take any days off. Peer-pressure is insanely strong in those environments. You are supposed to feel bad to letting your colleagues do the work, while you voluntarily (!) take time off. Especially at start-ups there is always something for you to work on. As an employee it's easier to agree on like 25 vacation days/year beforehand because then it's in the contract and both parties can point to it when there are problems. If a colleague has a problem with someone taking more vacations days, it comes down to their own inability to negotiate more days for themselves; not to some "backstabber" leaving their colleague behind for some fun. As I said, there are cases where unlimited vacation days work out but I would say those are the lucky 1%.