Yeah, well. This is America.

When I was a consultant, I could not find a health insurance plan that was even vaguely the equal of my current job's health insurance. Not too expensive, but simply not offered.

That's not to say that job insurance is automatically good -- the job I had before being a consultant had worse health insurance that was a little worse than the plans I had as a consultant.

Good luck with that... I don't know what your definition of "good" is, but in looking around when my cobra policy ran out, there were definitely limited options, none of which came close to what most of the worker policies offered, and none covered my retina doctor. The eye injections I get would be more out of pocket than my net income right now... and after 7 months out of work, I was seriously considering jobs paying roughly half of where I'd been the past few years just to maintain a good insurance plan.

I had about 12 months of buffer, but several unplanned home and auto repairs ate into that.

Healthcare isn't much of a differentiator in the kinds of jobs being discussed here. Pretty much all of them will have good healthcare plans that are as close to free for the employee as the IRS and insurers will allow.

You still have to interact with the insanity of the American healthcare system, but you're not being financially ruined by it.

There are three situations from what I've seen, one is toxic workplaces where PTO is closely tracked and people who use it are punished (socially or otherwise). That happens more often in unlimited PTO places, but absolutely happens in places with traditional PTO plans too. Second you have the more common situation where without a use-it-or-lose-it resource people end up taking less PTO than they would normally, this happens naturally A LOT. Third are people who have never worked somewhere with unlimited PTO who are justifying to themselves and others why it's bad :)

I believe it's not intended to be a trap; it's not to encourage taking more or less than a typical amount. Rather, it's done to avoid paying out on termination in places that require doing so as mentioned earlier.

FWIW, no I have not worked in a place with unlimited PTO. Heard a lot of negatives though and that's what scares me off it. The peer pressure to not take PTO would make it difficult for me to actually relax. Everyone is different though and I'm sure there are places where it works. But it's hard to determine that during the interview process. So I'd rather have the guarantee of x number of weeks of PTO where x>5.

Agreed. I was skeptical at first, but I've worked at several companies with unlimited PTO and they all specifically encouraged people to take time off. One place was explicit that the reason they switched to unlimited was to get people to take vacations: "PTO is not meant to be a bonus when you leave the company. We want you to rest and recharge."

My current company recently made a rule that you have to apply for time off through the HR software. Not make it harder to take PTO—all requests are auto-approved-just so HR can track it. At the next all-hands the CEO said something like "You guys work really hard... we're, uh, worried." My manager has been bugging me to take a proper vacation instead of my usual day off here and there.

There are certainly awful, exploitative workplaces out there. But there are also great companies run by good people.

I've heard from friends who worked at an "unlimited" place who said there was a soft threshold at 4 weeks. If you took more than that your boss would very quickly give you a call to discuss it.

Depends on the work culture certainly. Unlimited is, if course, not really unlimited. But whether (for a good performer) it's culturally 2 weeks or 6 weeks matters a lot. Even in an old-fashioned regular PTO company, I had people--though not my managers--incredulous that I would take 4 weeks of out-of-contact time.

More recently, someone I know who worked at a well-known unlimited PTO company told me that a newly hired head of corporate communications quit in short order because the CEO would actually go radio silence on vacation and they couldn't deal with that.

I've only heard bad things about unlimited PTO, but I've only experienced good things. I've worked at two places with unlimited PTO, and at both, I typically took ~5 weeks and nobody had an issue.

At one place I worked at, they only gave 3 weeks, but with the option to "buy" a 4th week with a slight salary reduction that effectively made that 4th week unpaid, but with the loss of pay spread out over the year. It was nice, though I actually wish I could have taken more, especially since the company did a shutdown between Christmas and New Years and forced you to burn a week of PTO at that time, which meant that you really only got 2 or 3 weeks throughout the year to do what you wanted.

It is fairly common, it has been my experience and that of others I talked to, that unlimited in many companies means that you can take 3/4 weeks per year of time off, but you need the authorization of your manager or HR for any additional day. Which is not unlimited, but that's the word these companies use.