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Is unlimited vacation a perk or a pain? Here’s how to tell

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To some, an unlimited vacation policy conjures up images of month-long European getaways and guilt-free staycations. To others, it can be a source of endless anxieties.

If I take two weeks off, will my coworkers think I'm a slacker? Is it okay to vacation more than my boss? Have I really worked hard enough to deserve a vacation?

I get it. For almost a decade, my company offered unlimited vacation time. As we grew to 40 employees, questions like these began lingering beneath the surface — particularly among our junior employees. Last spring, my executive team decided it was time to put the policy up for a vote for all of our employees to decide.

When my staff ultimately decided to strike down unlimited vacation in favor of a more finite policy based on tenure, I can't say I was surprised. The problem is that unlimited vacation isn't as obvious a perk as, say, a bottomless keg of cold brew coffee in the kitchen. It's much more nuanced.

If you're considering a job that offers unlimited vacation, take a step back and consider these three questions first:

1. Will you actually take time off?

If the idea of having to decide how much vacation time you deserve sounds stressful, you probably won't thrive under an unlimited policy. Accruing vacation days, and being incentivized to actually use the days you've earned, may be a better fit.

Even as CEO, I can attest to this. Under our unlimited plan, I realized I was only taking a yearly total of about two weeks off. Under the new plan, I'm planning to use most if not all of my five weeks. To me, the fear of losing these days I've "earned" is what's motivating me to actually use them.

Two psychologists in the 1970s dubbed this common human behavior as "loss aversion." When we're faced with losing something that's been given to us — like vacation days that expire — we'll do what we can to avoid losing it. And so, we take a vacation.

The "use it or lose it" rule built into many traditional policies is perfect for employees who don't prioritize taking time off. In an unlimited vacation setting, this very real need to relax and recharge often falls by the wayside. And that's upsetting, as taking a vacation can actually improve your health and well-being, and alleviate burnout.

2. Does the company even want you to vacation?

It's becoming a Silicon Valley trope that when a company advertises unlimited vacation in a job posting, you can probably expect to be working around the clock.

Most employers justify the demanding hours by saying things in the interview process like, "Our employees work hard, so we want them take as much time as they need to recharge." But some managers don't always take steps to ensure that each team member is actually taking time off.

And that's a problem. In fact, a recent study by the U.S. Travel Association found that 66 percent of employees felt that their company culture was ambivalent, discouraging and sending mixed messages about vacation time.

In the interview process, it's perfectly acceptable to ask the interviewer about whether managers support every employee's need to take time off. If you get the sense that there aren't clear mechanisms in place to do just that, it may be a red flag.

3. Are the lights really out at 6 p.m.?

When I hear about companies like Netflix and GE that have managed to preserve their unlimited vacation policies, my hunch is this: They most likely rely on their company culture to enforce soft norms about what an appropriate amount of vacation looks like. While they may boast about "trusting our employees," what they really trust is their culture.

One of our junior employees recently confessed that while she loved bragging about our unlimited vacation policy to family and friends, she was hesitant to take too many days off. "It's all optics," she told me. "When I first started, I got a sense of how many days people typically take and tried to match that." Today, she's taking two weeks more than she would have under our unlimited plan.

If you get a sense that the company is filled with workaholics and martyrs who brag about pulling all-nighters, be on high alert. Chances are that cultural pressures may stifle your confidence to take the time you need.

Josh Millet is the founder and CEO of Criteria Corp, a pre-employment testing company.

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