Becoming A Remote Worker

I realized this week that, without really thinking about it, I joined a growing society of people who travel around the world, working from unique “offices” (read: the beach, a surf hut, the desk you poorly constructed to watch your children swim in the pool while writing a policy document...) while experiencing and engaging in new cultures. I've always envied the people who do this; mostly singles and seldom family people. But, here we are in Portugal – I'm working from a surfing lounge – with six kids, a wife, and a dream of doing this for at least a year or two. Perhaps we'll find a new home while we travel and we'll settle in but, in all likelihood, we'll travel to half a dozen countries over the next two years before settling into something more normal.

I've been a “laptop hobo” for many years, preferring the white noise of a hipster coffee shop to the potential monotony of an office, but I've always had a home study or office desk to be based out of. I don't yet know what this adventure will entail but, as we get started, I thought I'd share five tips on becoming a remote worker.

  1. Get the Right Tools (and keep them minimal) - Seriously, keep it light! There is an allure in having a lot of technology, and it's easy to go a little crazy (check out Woz's bag!). Make sure you've a good roaming plan on your phone (or go unlocked and get a local SIM). Get a light laptop (seriously, do you need all that power?!). I prefer the overpriced yet incredibly simple and elegant MacBook. Be sure you can jump into conference calls whenever you're needed, or others will quickly become frustrated with your workation; you really don't want that!
  2. Ensure You've the Right Job - We tried to do this a couple years ago; well, we kind of tried to do this a couple years ago. We moved into a friends beautiful cottage out on a lake and I setup shop in the garage. It's was a lovely rustic setup and I couldn't have been, more excited. At the time, I was working as a CXO for a great startup (Two Hat Security) hellbent on saving the internet from trolls and toxic users. At the beginning, the remote work was working well enough but, as the year went on, I was required in the office more and more. The result was spending my weeks in town and then returning to the cottage on the weekends. As lovely as it was, I wasn't so much a remote worker, I became a remote dad.
  3. Become a Pilgrim - My friend Corey wrote a paper about the difference between a tourist and a pilgrim. It's excellent and you should ask him if you can read it. Basically, tourists consume and pilgrims preserve and absorb. If you're going to become a remote worker in a foreign land, you can't just expect to consume a culture and become better for it. That's like saying that binge watching Friday Night Lights will make you a better American football player. Rather, seek to preserve the culture and blend in as best you can. When you can't blend in, be honest about it and allow the locals to teach you what it means to be local.
  4. Be of A Like Mind - If you're looking to do this solo, feel free to skip to the next tip. For those of you looking to travel with a partner, friend, or family, be ready to experience significant disruption to normality. You can read all the Lonely Planet books you want but nothing can prepare you for your first adventure in a non-English speaking country where things are just different from what you're used to. If you're prone to suffering high volumes of stress in your relationship when challenged by new things, consider working on that first.
  5. Adventure & Purpose Await You - People have been asking us recently why we're doing this. There are a couple of easy answers but they'll end up being lies if we don't actually take up living while we're exploring. It's incredibly easy to find a monotonous routine within a completely different culture. For example, we've now been in Portugal for 3 days and we've completely lived in this one stretch of land between the beach and our villa. It's a great stretch, but it's what you do when you're on vacation (or you've created an entire community within this small area). It's unlikely that we'll learn to live within this culture if we don't find a community to engage with while we're here. That's scary though, especially as we've no easily identifiable place to start building this community from. Within the next couple weeks, we'll rent a vehicle and begin to expand our boarders. As we do this, we'll hopefully find a place to actually plug in. Perhaps it will be through a language school or maybe through a surf school. Perhaps we'll find a church to attend or some community group which meets regularly for whatever reason. The point is, adventure and purpose aren't found by hiding, they're found by living and being bold. My wife's friend recently sent her a quote. Beautifully illustrated, it says, “Be you boldly”. When in a new culture, that needs to be lived out carefully as sometimes our boldness becomes arrogance in a culture yet unknown to us. But, assuming you carry with you the heart and humility of a pilgrim, boldly go and become a cultural ambassador for both the cultures you've already learned about, and the culture that you're now a remote worker within.