How an Unlimited Vacation Policy Convinced Me to Give up the Freelance Life for an Office Job

I am writing this post from an RV, somewhere between a pristine glacier and the frigid ocean on the eastern tip of Iceland. I’m not just telling you this to make you jealous, I promise. It’s to highlight a point. I live and work in Southern California, so geographically and culturally, I am far from home. But mentally, my work travels with me. Now, before you judge the girl who can’t switch off on her travels, consider this: I work for a company that has created a culture defined by flexibility. What does that mean exactly? In our case, it means that vacation days taken are not counted — (yes, you heard that right, there is technically no limit to the amount of vacation you can take) — and there are no set office hours, with work done at home and work done on site given equal value.

Not only is this progressive and aligned with today’s technological advancements that mean anyone can work from anywhere at any given time, but it is also the reason I finally took the plunge and accepted a full time “office” job after nearly 15 years of working as a freelance writer and marketing consultant.

I’m not going to lie, I loved working as a freelance contractor. I felt like it gave me the best of both worlds — the ability to work with a variety of clients, turn down ones that I didn’t want to work with, pick and choose when I wanted to work (some of my best work has been done at 2am), and, most importantly for me, travel when my kids had time off school. But cracks were starting to reveal themselves beneath the surface… My income would vary dramatically from one month to the next, I could feel isolated through a lack of collaboration, and I often felt like I had more to contribute to the companies I would work with than a short term project allowed.

This seismic shift was taking place just around the time I was referred to a company that was looking for a copywriter/marketer. I was immediately drawn to the culture. It was dynamic, collaborative, fun, and intensely productive. The crew I was working with were utilizing their combined expertise to evaluate businesses, help them refine their model, create killer go-to-market strategies, and ultimately accelerate their success. I loved what I was seeing. I wanted IN. But I didn’t want to give up my freedom. “Oh yes, she who wants it all”, right? Well, not exactly. See, my work life and my personal life have always blended into one. My laptop is a full time appendage. It travels with me on mom duties at the soccer field and on snowboarding vacations to Mammoth. It is a common feature on weekends and late at night when the house is silent. And yes, it even makes a solid appearance while road tripping in Iceland.

So why relinquish the lifestyle I had worked so hard to claim? Well, just like the guy who thinks he will be single for the rest of his life then finally meets his perfect match at 40 years old, I realized I might just have found mine with this company that embraced a flexible work culture and believes that a happy team is a solid team. It took no time at all for me to accept an offer for a full time role, and I haven’t looked back since.

But how can a company be productive when its employees are off galavanting around the world and never in the office?”, I hear you say. Well, like everything in life, it’s not a straightforward answer, but for it to be successful it means understanding the following:

  1. FLEXIBLE CULTURES NEED FLEXIBLE EMPLOYEES Ideally this will be someone who is used to meeting the demands of work no matter when that is, with weekends, late evenings, and the occasional vacation check-in not entirely off the menu. If you are the kind of person who would prefer to clock in at 9 and out and 5 and find the prospect of dealing with some late-evening-proposal-polishing offensive, it’s probably not for you.
  2. THIS IS A MUTUALLY BENEFICIAL AGREEMENT Employ people who respect the culture, and realize that rather than a one way street of freedom, it is actually a mutually beneficial agreement that allows you to take your kids to soccer practice in the afternoon so long as you finish your project after dinner.
  3. HIGH PERFORMING EMPLOYEES SELF-ENFORCE BY DEFAULT High-performing employees simply aren’t going to be abusing a vacation policy by leaving the country every other week. They are here to do a job and they want to do it well. In fact, studies have shown that employees actually take fewer vacation days in companies that offer an unlimited vacation policy. As Patty McCord from Netflix — a leader in flexible company culture — once said, “There is also no clothing policy at Netlix, but no one has come to work naked lately.
  4. A FLEXIBLE WORKING CULTURE USUALLY INCREASES PRODUCTIVITY In today’s world of omnipresent internet connectivity and creative roles that thrive on external stimuli rather than staid office environments, a flexible working culture more likely increases productivity than threatens it. It’s hard to come up with the next big thing in advertising or be inspired to create a content campaign within the four walls of your office building. In fact, some of my best creative moments have come while swimming laps in my pool!

The legacy company set up is, quite frankly, a threatened species. Clocking in and clocking out, two weeks paid vacation, and concentrating on time spent at desks rather than results simply has the focus all wrong. When you love what you do, you want to do it well. And when you achieve a work-life balance (and yes, that does sometimes mean working all Saturday or getting back on some projects while on vacation), the divide between the two parts of your life starts to fade.

I’m not saying there won’t be casualties. There will be those who don’t get that with freedom comes accountability and they will abuse the system. But that just becomes part of a company’s natural attrition process. My guess is that little by little, companies that embrace this philosophy will start to recognize the right personality types at the first interview. And on the flip side, they will attract an increasing number of top level candidates who work best (or will only work) in a flexible office culture.

For me, meanwhile, I will continue to respect the culture of the company that finally got me to commit and hotspot my phone to my computer from an RV in the depths of Iceland.