Vacation On Their First Day

We Ask New Employees To Take A Two-Week Paid Vacation On Their First Day.

By Jason Freedman, 42Floors

Vacations have always been hard for me. It’s a weird thing to say, but it’s true. They just don’t come naturally to me.

I remember when I was in business school, all of my classmates were taking these epic vacations seemingly all the time.

Spring breaks in Costa Rica, pre-internship trips to South America… I saw the pictures and they did look like fun, but yet each time I stayed home to work on my startup.

This was back in 2007 when I was running OpenVote, which was a web 2.0 Facebook app company.  That went nowhere. After two years of making no money for the company, spending all of my investor’s money, and wasting away what little cash I personally had, those pictures of everyone else’s vacations were painful to look at.

But when we finally turned the servers off for OpenVote, I didn’t make up for lost time and go on some sweet vacation. Hell, I didn’t even relax for a few days. I was so in debt and so frustrated with failure that I got right to work filling as many hours of the day as I could with random consulting jobs.

And, wouldn’t you know, less than three weeks later, we had stumbled upon Flightcaster and off I was starting another startup. The time for vacations had passed once again.

I always thought my issue with vacations was just some internal restlessness. That is until I started 42Floors and my good friend Dana told me his version of the exact same story.  There is something about vacations and startups that just don’t work well together.

Forgive me for generalizing…but at a big company, you are trading your time and passion for compensation. Vacation is time off. It’s paying for 11 scoops and getting the 12th for free.

But startups are different. Startups are a mission; a belief that something impossible is actually possible. It’s being part of a team that is working toward some distant horizon. It’s this competing against the impossible that makes it so much fun. Your coworkers are your friends. It’s so much closer to a life style than a job that taking a vacation from your startup doesn’t have the same connotation.

But that doesn’t mean startup people don’t need vacations – we clearly do. If for no other reason than our best ideas come when we’ve been able to disengage from the problem in front of us. Vacations are a change of scenery. They’re a chance for perspective. They’re quality time with our friends, family and significant others. They’re a chance to see the world, to waste away the day reading books, playing chess, trying new things. Vacations are 100% essential.

At 42floors, we created an unlimited paid time-off policy. Everyone takes as much as they want whenever they want. Because we’re smart, motivated, responsible people, we don’t have to worry about this policy being abused.

But here’s the kicker: unlimited time-off doesn’t work.

While the unlimited paid time-off policy works for some of the people some of the time; it still feels too hard to get away. It’s not the social pressure part. We’ve worked really hard to promote vacation-taking in the company. It just comes back to the fundamental issue that vacations for startup people are hard.

So we have been searching for ways within the company to address it, and we’ve come up with a really good one that I thought I’d share.

Everyone Needs a Pre-cation

At 42floors, we heavily, heavily recommend that all new people take two weeks of vacation starting exactly on their first official day.  What this means is that when you get a job offer from us, you’ll pick a start date. And that’s the day we start your payroll.  And that’s the day you leave for vacation.

And you get to take that time to transition from one chapter of your life to the next. If your startup just failed or you hated your last job, you get a couple weeks of mental and physical recovery. If you have a significant other that’s been dying to get away with you, you can go away someplace nice knowing that your first paycheck will be waiting for you when you return.

You’re mentally free to completely let go. Vacations when you’re searching for a job don’t work great because you feel the pressure to find a new job. Vacations in the middle of a job are tough because you have the urge to check in. But vacations between jobs with a signed offer letter in your hand, those are the absolute best. The only thing that holds people back from taking advantage of this perfect time is that it feels awkward to ask.

And so that is why we had to make precation a policy in our company (we would make it actually mandatory, but we have this thing against telling people what to do in our company). Thus far there has been 100% adoption.

Precation doesn’t solve everything, but it’s at least a way to start off on the right foot.  If you’re a founder of your own company, think seriously about implementing this.  You won’t regret it. If you’re an employee in a company, chat about this on Hacker News and, hopefully, enough founders will see it that it could become a thing in the startup world just like free lunch and no start times.  And if you’re looking around for a new gig, well then obviously come check us out at 42floors.  We’ve got like a gazillion roles open and we’d love your help.

Read more on Jason Freedman’s blog

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