Blogs from the Ranch

< Back to Our Blog

Working Vacations


Chris Kelly

As you’re probably very well aware at this point, Highgroove is a Results Only Work Environment which means that it doesn’t matter when or how we get our work done, as long as we get it done. This means that working from the beach is okay! Awesome!

While working from the beach seems like a great idea, we’ve iterated a bit on working vacations and have some things you should read if you’re considering combining a vacation with getting some work done. Read on for the details.

Most companies have a strict vacation and holiday policy. You get some number of specific holidays off per year, and a set number of vacation days which you slowly accumulate and get to spend on being completely disconnected from work. At Highgroove, we have mandatory unlimited vacation, and ‘optional’ holidays. If you’d like to work on New Years Day and take 2 weeks off in February to take the longest nap ever, that’s completely ok and your paycheck will be the same.

That said, taking time off is weird! We’re all here to be super productive and we do keep everyone’s schedules pretty booked, so if we take time off it means pushing back some deliverable that a client is waiting on. This is almost always ok, and most of our deadlines are estimation based and not need based, but the temptation to ‘get some work done’ while on a family trip is pretty strong. NPR did a story a while back: Unlimited Vacation Time Not A Dream For Some which included a common thing we hear:

Some critics worry that in a culture of workaholics, unlimited vacation might really mean no vacation; that without a specified time to be “off” employees might feel pressure to always be “on.”

Especially in our field, this is a common feeling because people have smartphones or laptops with them most of the time, and everyone on the team is working a different schedule so 24/7/365, at least one person on the team is delivering value to a customer.

The answer to this is planning to work while on vacation! We tried this out, a handful of people have done ‘working vacations’ and the almost universal feedback is that this is a Bad Thing. Some thoughts:

Working while on vacation is a bummer: When you get somewhere and have the intention of working, something else you want to do always magically appears. You can’t just go do it and say “Tomorrow I’ll work twice as much.”

My trip was just weird because my girlfriend was trying to get me to do stuff during the day, but I just had to work.

Don’t think it’s going to be easy, Because it’s not. It will diminish the enjoyment of vacation, until you get comfortable.

Everyone that has taken a working vacation has gotten less work done than they planned, and it’s negatively impacted what should be a time of relaxation. That said, there is a way to make this work which involved being more structured and setting lower expectations. If you plan ahead for everything you need (quiet, space, time, internet, etc) and can ‘draw a line in the sand’ and block out specific blocks of time, there is a pretty good chance you can take a slightly longer trip and get some work done. Plan to work for 3 hours in the afternoon each day during the hottest part of the day, between a morning at the beach and happy hour. Let everyone you’re with know what this means and make sure that they’re off having fun without you or reading a book on the porch.

You can probably make a working vacation work, and over six days of your vacation you might get done as much as you would have in three days in the office, but when it’s all said and done, it’s probably better for you to just take the time off and relax. You’ll be more effective when you get back! ROWE puts you in control of how you get work done so you’re welcome to experiment, but I know I’ll be going off-grid on my next trip.


Chris Kelly