There is no such thing as unlimited vacation time. If you want to know how much vacation time you have, ask your HR manager at your “unlimited vacation” org how much vacation they’re required to pay out by law if you separate from the org.
Anecdotally I worked at VMware and Dropbox when they rolled out these policies. I took about the same vacation time as I had used previously and the difference was mainly that I wasn't owed any vacation money when I resigned.
The average worker has no baseline for what amount is appropriate. They think they are always too busy. Their boss thinks they are too busy.
But some people get more by being untransparent. If I’m going on a fishing trip, I don’t tell anyone. If something comes up, “I’m out of the office, I can meet when I get back or do a call.” Nobody knows if I’m traveling for work or vacation.
Untransparent...mmm...I think I like I that word :)
By giving a vague answer the allow themselves the option of pretending like the workload and projects did not allow it at the time you were going to take your vacation.
It's dishonest at best and a devious dark pattern at worst.
I had a co-worker recently who started counting up the time they'd taken off in the last year, realized it was much less than the industry average, and took off for Australia. Seemed like a very reasonable response to me.
This is false; you're misunderstanding the concept of accrued vacation. If you work for a company with accrued vacation (aka accrued PTO), you must be paid for it when you leave...for any reason including involuntary termination. But at a company with unlimited vacation, you don't accrue vacation days, so they don't need to pay you anything for vacation when you leave. Companies do this because they don't have to treated accrued vacation as a liability in their financial statements, so their financials look better.
The flip-side is also that they can't cap your vacation time, and indeed capping your vacation time could trigger a DoL investigation. Additionally, in some states like Illinois, the company must make vacation payouts equal to the amount of vacation the employee could have taken. (No guidance on this but lower level rulings suggest that it's at least the "capped" amount.)
There's also FMLA issues with unlimited leave most startups don't realize. (If you have unlimited vacation, you must pay out 12 weeks under the FMLA. If you offer paternity/maternity leave and accrued vacation, you only have to pay out pursuant to your leave policy.)