Why Unlimited Vacation is Poisonous Chicken Soup for the Soul

Larry Port
2 min readOct 3, 2014

Enough of this unlimited vacation nonsense. For the love of all that’s holy, vacation days should be clearly defined, and they should be mandatory.

I take time off extremely seriously. I’m an entrepreneur with a relatively new software company and am a big believer in vacation. So much so that I built my company in a way that I could take two weeks off and not have to check in with the office. I give entry level employees three weeks off, half-day Fridays in the summer, and all sortsa holiday days.

Before all you haters out there say we can’t be getting anything done, guess again. We move heaven and earth at this company. When we’re here, we bust ass. We’re incredibly capital efficient and productive. We pound out more product and marketing than our well-funded competitors.

Look, this is a simple truth. We all work better when we’re refreshed. Not just a little better. MUCH better.

I mean, who doesn’t return to work with renewed energy after taking a walk down one of these:

How can people not work better after a walk along one of these?

Rebooting is important. Just look at Windows!

So when Sir Richard Branson’s new unlimited vacation policy added a managerial +1 to the concept Netflix made popular, I winced.

My gut tells me that this approach will lead employees to take less time off, not more.

Consider the following: let’s say you have three weeks of vacation that you are required to take, which is what entry level employees get at my own software company, Rocket Matter. How many days off will you have, excluding holidays? Fifteen.

What if you have unlimited vacation days? Will you take fifteen as a kid right out of school? What if no one else is taking fifteen days?

The number of days taken off will ultimately be dictated by social proofing and by whatever forces in the office are seen as advancing a career. If the people who don’t take a lot of vacation rise through the ranks, and you WISH to rise through the rank, you’re screwed. No vacation for you.

My thinking? If you’re an entrepreneur considering unlimited vacation, at least have the balls to provide a minimum number of days to be taken.

If you liked this post, please share it! If you’re another entrepreneur, please reach out to me. If you’re a lawyer and need legal software, check out my company, Rocket Matter!

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Larry Port

Father, Husband, Founder and CEO of Rocket Matter (@rocketmatter). Talk to me about reading, history, health and fitness, and running a software company.