My company has "unlimited" time off and it was a red flag for me before joining. The thing that got me past the red flag was that both founders saw it as their

My company has "unlimited" time off and it was a red flag for me before joining. The thing that got me past the red flag was that both founders saw it as their responsibility to set the standard for the amount of holiday taken, and would take significant holidays in order to define the culture. The thing I've enjoyed most about "unlimited" holiday though is not the length, but the fact that I don't need to differentiate between holidays and sickness. That may sound like an obvious distinction, but it's not. Sometimes I know that for my own (mental) health I need a day off, but I'm not _sick_, it doesn't need to be a specific day, it could be any day in the next week maybe. Justifying it as a sick day would be tricky if there is a distinction made, and taking it as a holiday is a bit unfair on the employee because it's not really about the holiday. Unlimited time off means there is no distinction and you can just do it without thinking about it. Another thing that improves our approach is that while we don't technically have a minimum (there are guidelines), if someone leaves they are entitled to 4 weeks paid leave in their last year and we make this up in time/salary to ensure leavers don't lose out. Last time I checked we hadn't actually had to pay anyone as all leavers had taken enough holiday. It takes a lot of discipline to get right, and so it's still a red flag for me, but it's one that can definitely be overcome and can be a strong positive if the company has the right attitude.