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‘Are Unlimited Vacation Days Really Unlimited?’

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Dear Boss,

I have a friend who started a new job recently. She had been laid off during COVID when her company had to eliminate about half of its staff. Given what she had told me about how she acted at work — routinely leaving early without making up the hours, refusing to ever work late, and generally acting like she was doing the company a favor by being there — I was not surprised that she was one of the people laid off.

When she started her new job after a few months of unemployment, she was really excited and kept talking about how hard she was working and how many hours she was putting in. But for the last few months she’s been taking a truly crazy number of days off. Almost every week, she tells me she’s taking a day or two and always says, “It doesn’t matter, I have unlimited days.” She also claims that she frequently works “really late,” but based on the hours she’s described, it sounds like she’s only working a little beyond the typical 9-to-5. Then the other day, she told me she’s “barely working” over the next month or so because she’s taking off multiple days per week to extend various weekend trips and holidays. This alone was a bit worrisome to me, but I became more concerned when she added that she’s taking more days than everyone else, and that her co-workers don’t take advantage of the unlimited days. I tried to gently ask how she’s able to get so many days off, saying that most people I know who technically have unlimited days aren’t able to actually take as many days as they want. She clearly got offended and replied, “Well, I’m allowed to do it and my boss hasn’t rejected any of my requests yet.”

So, first, is it really acceptable to take a ton of days off if you technically get unlimited vacation days, or is there some kind of implied limit?

And second, is there a better way to broach the topic with my friend? She did not grow up around anyone who worked in a traditional office job, and over the decade we’ve been friends, she has frequently been shocked over basic office etiquette (for example, how deferential you have to be to bosses, how much notice you typically have to give for days off, business-appropriate attire, etc.). I don’t say that to be mean or judgmental! I would hate to see her get laid off again or have another professional setback because of this, and I don’t think any of her family members have the relevant experience to think this is odd or set her straight.

I’m also selfishly curious as I start my own job search, because if this is actually normal then maybe unlimited vacation days should be higher up in my search criteria.

Unlimited vacation days can be really weird.

They sound great in theory! Who wouldn’t want unlimited vacation? The problem is that it rarely works that way in practice.

In fact, there’s research showing that, on average, workers with “unlimited” vacation time actually take fewer days off in a year (13) than workers who are given a specific number of vacation days (15) … and twice as many of those with unlimited time off say they “always” work on vacation. That’s most likely because, without clear guidelines, people become unsure about how much time off is really okay to take and how much will be seen as excessive. Not wanting to be seen as slackers, they err on the side of caution and end up taking less time than they’re entitled to.

Another drawback to unlimited vacation time is that you can’t save up any paid leave — which means that you wouldn’t get the cash payout you might otherwise receive if you left your job with accrued vacation time remaining. (Not every company pays out accrued leave to resigning employees, but many do, and many states require it.) In fact, that’s been a major incentive, if not the incentive, for employers to switch to unlimited leave; it can end up saving them significant money in the long run.

The most interesting thing (to me, anyway) about unlimited vacation time is that it requires managers to truly manage their teams. They need to be assertive about encouraging people to take time off if their workloads allow it, and recognize and address it when someone’s workload never allows it. They also must be forthright if someone is abusing the system — and create a shared understanding of what that would even look like. Generally that’s something like “as long as you’re meeting your goals and not delaying anyone else’s work, you can manage your own time off as you see fit” … but that can be trickier than it sounds, particularly if employees’ work goals are unrealistically ambitious or if the work environment is so fast-paced that time off means you’ll always be delaying someone else’s work. That can lead a team’s most conscientious employees to feel like they can’t ever take time off responsibly, or can only take very little. Managers have to be really hands-on and fair-minded to effectively manage a team that has unlimited vacation time — and many aren’t.

That brings us to your friend. It’s possible there’s more to her situation than you know (like a health problem, an unusually slow period at work, or an explicit conversation with her manager affirming this is okay), but it sure does sound like she might have a fundamental misunderstanding of how this all works. If that’s the case, her manager is deeply in the wrong for not explaining it to her … but there are plenty of negligent managers who avoid having even mildly unpleasant conversations, and unfortunately that won’t save your friend, if at some point the company gets fed up and decides she’s taken it too far.

In theory, I suppose it’s possible that your friend works at the one company in existence where “unlimited” vacation days truly does mean unlimited, without regard for one’s work. But that seems awfully unlikely. Typically employers have hired you to do a job, they want you there doing that job, and “unlimited” includes the unspoken subtext “within reason and as long as your work is getting done.”

As for how you might broach this with your friend, it sounds like you’ve already tried. I’m not sure there’s much to be gained from trying again! It’s a kind impulse to want her to understand how this might be perceived and that in most companies it could lead to her being let go. But you’ve already raised it and she got offended — which seems like a pretty clear “butt out” sign. The one exception might be if you have a very close friendship and you frame it as, “I won’t bring this up again if you ask me not to, but I couldn’t forgive myself if I didn’t say something now and you ended up getting fired.” If you go that route, make sure you’re direct — no hinting around, just bluntly saying, “In my experience, unlimited vacation isn’t really unlimited, there are implicit limits, and you can get fired if you repeatedly take a lot more days than everyone else.” But from there, you’d need to back way off and accept that how she navigates this is up to her.

Order Alison Green’s book Ask a Manager: Clueless Colleagues, Lunch-Stealing Bosses, and the Rest of Your Life at Work here. Got a question for her? Email Her advice column appears here every Tuesday.

‘Are Unlimited Vacation Days Really Unlimited?’