5 Secrets To Making “Workations” Productive

One of the best things about building a technology company is the ability to work from much anywhere. One way to take advantage of this is to go on a “workation“. I took my first workation three years ago when I decided to spend six weeks in Canada over the summer. The plan was to work in the morning, enjoy the boat in the afternoon, and finish up anything at night. To my surprise it actually worked quite well. Since then I’ve done a half dozen and feel blessed to be able to live in a world where this is possible. Here’s some secrets I’ve learned along the way to make them productive.

1. Find A Great Location

To have a productive workation you need to find a place that not only has amazing sights and weather, but great internet and a place for you to work. Once you’ve decided on your destination, I would recommend using AirBNB or VRBO to find a real apartment or condo. Having your own place – instead of staying on a resort or hotel – will definitely help you stay focused on the “work” part of the day. Last year we did a week of Kiteboarding in Aruba, and this year (where I’m writing this from) we’re in Exuma, Bahamas. Both places have great internet and desks for Renee and I to work from.

2. Structuring Your Day

The plan is to get up get started early. If you’re looking to maximize your time, you’ll do start with something active, then get working on the most pressing projects. Here’s how I structure my day.

  • 6:30AM – Workout / Run
  • 7:30AM – 12PM (Noon): Team meetings, complete major projects, calls
  • 12PM – 6PM: Activities or just relaxing
  • 6PM-8PM: Dinner (In-house or nice restaurant).
  • 8PM – Bed: Emails, review projects, paperwork
There’s always exceptions to the schedule but in general this is schedule has proven the most engaging and productive.

3. Make Your Health A Priority

As I mentioned above, I like to start my day with a workout. If you’re in a place that warm, you’ll want to go out before the sun start beating down on you. One downfall I see happen many times on “vacation” is to let loose and eat like a pig. I actually take the opposite approach and leverage the time away to get back into a routine and feel good about my health. Kicking off your day with a workout also makes for a very productive morning.

4. Communicate With Your Team

Since I’m physically away from the office, I usually turn to Skype Video (1-on-1) or Google Hangouts for connecting with the team. Video lets everyone see you – which I feel is super important. I’m big on transparency and I don’t hide my schedule. If I’m going to be around in the morning, then gone surfing in the afternoon, then I tell them. Whenever possible I also try to keep up on emails so that I can help move things forward – even if I’m sitting by the pool.

5. Work Hard, Play Hard

The whole point of a workation is to work hard, and play hard. I’ve always been an adrenaline junky, so I’m trying to plan my trips around extreme sports. Either snowboarding, snowkiting or wakeboarding. I always opt-in to connecting with a local to fast track your experience and quickly get the lay of the land for the area you’re in. It might cost money, but it’s usually well worth it in the end.

Those fives secrets have helped me not only be more productive and see the world, but also come back to the office feeling recharged and not overwhelmed.  Will this scale once the family grows? I’m confident we’ll make it work.

Let me know if there’s any locations or tips I should consider for my next one!

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