I'm a cynic about unlimited vacation policies for a few reasons: 1. At its core, I believe it's a clever bit of financial engineering disguised as a worker-fir

I'm a cynic about unlimited vacation policies for a few reasons: 1. At its core, I believe it's a clever bit of financial engineering disguised as a worker-first policy. All of a sudden your startup doesn't have any accrued PTO to keep on the books, and doesn't have to pay out anything to people who leave (I know this varies state-by-state but at least in CA I got paid out at previous jobs). 2. There's no tangibility to your vacation. You're just given access to this nebulous thing and it is up to you and the company to define a culture and a policy for it, and most of the time they don't do it well. People end up coming up with a "virtual bank" in their heads to justify taking time off and keeping track of things. This leads to totally different value systems between individuals, teams, managers, etc. All of a sudden a number I could look at in my payroll software and was inarguably whatever integer it was to anyone who looked at it is now some weird "idea" that my boss and I have to agree upon, potentially every time I go and take time off. This leads to unfair application of policies across a business, because every employee and manager is different. 3. In an unlimited system, the value of 1 day and 1 week has to be self-assigned by me or my manager, since with "unlimited" the value of any individual day is by definition basically zero. I think this leads people to see their time off as less valuable and are more likely to come online to check an email or respond to a slack. At my current company we have an unlimited PTO policy, but they found people weren't actually "off" when they said they were, so we now have one day a month that is dedicated as a company holiday so that everyone is off at the same time. It's usually used for creating a 3 day weekend, or extending a federal holiday. Overall, I hope the policies continue despite my cynicism, but only with more guardrails. I hope that companies have better policies in the future encouraging employees to take time off. I would like to see companies do more "full shutdown" days like mine currently does. It's a forcing function that benefits everyone.