Unlimited vacation is a bad idea
I used to love the idea, but after having it a few years, I've changed my mind. Even though I had unlimited vacation, I don't think I took nearly enough time off.
Not taking enough time off is what inspired the title of this post. Of course you can't take "All" of something that is unlimited. Yet, I would frequently feel short changed on vacation. I don't think it was anything intentional on my employer's part and I don't think it was entirely my fault. I lay the majority of the blame on the notion itself.
Why didn't I take more time off?
Asking for time off is still awkward. It feels like I'm putting everyone else out because someone will have to take over my duties while I'm away. Even if there are very few duties, there is still the fact that the output expected from me will have to be delayed. Maybe that's fine. But there's that part of me that is sure that even though everyone is saying and acting like it's fine, there's a little disappointment or even frustration below the surface.
And then there's the fact that in reality "unlimited" does have a limit. It's not like your employer would let you take the entire summer off every year or just take week after week indefinitely. At some point, they will decide your salary could be better spent elsewhere unless you start taking less time off. I don't like that the limit is unspecified, yet we all know it's there. Even worse is that the limit is subjective and will fluctuate depending on the manager and employee.
I never hit that limit. I have a feeling I never even got close to the limit, much less being asked to take less time off. Yet, I was never asked to take more time off either.
What I really meant
Unlimited admin time and sick days more accurately describes what I actually desired when I used to talk about unlimited vacation.
I like the thought that I can run errands as needed without having to cram them into lunch or keep detailed track of vacation hours every time I step out. I also like the freedom to skip out a little early from time to time, especially on Fridays. I do understand that even these freedoms could be abused and tolerance will still be subjective. But if the environment is open about expectations and the use of this kind of "admin" time, then everyone will be doing it and I wouldn't ever feel like I'm taking advantage. That and running errands or leaving early a couple days a week will rarely impact feature delivery.
Even though I rarely need sick days, I also like the thought that they aren't tallied in any way. When you're sick, just take the time off without consideration of any kind of yearly quota. If you're the type who frequently fakes being sick, I feel like everyone can usually tell and we're back to the subjective tolerance of your current boss. If you're truly sick though, even if you're the type who is sick a lot, then it's not like you're out enjoying your time off. No need to add to you misery by knowing that you're eating away your precious vacation time.
A better way
A friend told me the vacation policy of the Netherlands - government mandated minimum of 6 weeks per year. The interesting part is that if for any reason the employee cannot take all 6 weeks, the employer must pay the employee an equivalent amount in the form of a year-end bonus. This sounds very cool and really close to what I would consider ideal.
In my ideal world, vacation would be a range where the bottom number is a forced minimum and the top number is strongly encouraged.
Perhaps we could marry this ideal world with Netherland's approach. Anything below the top number would be paid out. But again, the bottom number would be forced.
Now obviously I'm missing a lot of scenarios that would need to be considered. My first thought would be small businesses. Secondly, who is forcing the minimum? The government? Or would it just be the policy of forward thinking companies. Maybe it would be the thing all the cool companies start doing - just like unlimited vacation is the cool thing now.
I don't know the perfect solution. All I know is that unlimited vacation hasn't worked out so well for me.