When is Unlimited Vacation Time a Good Thing?

Are these “cherry on top” policies as good as they appear?

Aaron Webber
3 min readNov 26, 2019

Happy Thanksgiving holiday to all of those celebrating in the US. I know one thing that many employees and workers I’ve talked to recently are thankful for — unlimited vacation policies.

There have been no shortage of articles over the past few months about the pros and cons of the “cherry on top” of personnel policies… the free lunches, the gym access, the unlimited vacations.

Are these policies truly as good as they appear?

Here are my thoughts: Their presence is better than their absence. The idea of free lunch, free gym, unlimited vacation, big hugs, massages in health care packages, whatever it may be… they are all wonderful and largely a (successful) recruiting tool, a culture optic.

But they aren’t as good as made out. Because your ability to use them is limited.

Let me give you an example.

My son got a job in college at a local company, where they had a cafeteria and offered free lunch. He was going to make $10 an hour plus get free lunch plus access to their gym, etc. He came to me and told me how excited he was; I was a tad more cynical. I knew that there is, to quote the phrase, no such thing as a free lunch.

After a couple months, I asked him how those free lunches were coming along. His response was “Oh, I think I’ve had one.” I feigned surprise, and asked how is that? My son told me he was too busy at work to have time to eat, and when he was off his shift, he wanted to leave and go back home, not stick around for a meal.

So again, that policy served its purpose for the company in that it enticed and excited potential employees to accept their job offer. But the reality was that the benefit was going relatively unused. It was just an optic.

I read an article about a month or two ago now that said companies with unlimited vacation policies have generally happier employees. But their employees actually take less vacation than those with a set amount of 10 or 15 days worth of vacation. Some companies with unlimited vacation policies are actually having to set minimums vacation days.

What you want to do as the HR department or the CEO or the high level executive is to create policies and cherries on top that are reflective of the culture and DNA you want to build. Are employees enjoying what they do? Do they feel they’re making a contribution? Do they get recognized for their good work, or vice versa, heavily punished for a mistake?

That’s what really matters, because if you don’t have a sundae, there is nothing for which cherries can go on top. Will employees care about free lunch or free gym memberships if they don’t want to be in your office to begin with?

Within the organizations I lead, I want to put as many cherries on top as possible. One of the goals I have for these organizations is for them to be high on the list of preferred employers in their area. Because that’s important to me.

If providing lunch, if giving unlimited vacation days, if offering free hugs once every couple weeks helps me get there, then I’m in.

But it matters more to me that the policies I endorse and put in place are a personification of the DNA and culture I want to present. If I can put a cherry on the top of that ice cream sundae as well… Hallelujah. Good job and well done.

So, if you do happen to receive a truly free lunch, please enjoy it.

Aaron Webber is a serial entrepreneur and CEO of Webber Investments LLC, as well as a Managing Partner at Madison Wall Agencies.

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Aaron Webber

Chairman and CEO, Webber Investments. Partner at Idea Booth/BGO.