Two Questions for a Remote Worker

I wrote this really clever piece a couple years ago about the tools one needs to be an effective remote worker, a term that has since come to be far more than a buzzword to me. I wrote about how important it is to find a nice small computer, have a stable mobile connection, and some good headphones to block out the extra noise. At the time, we were staying in this beautiful village north of Lisbon in Portugal. It was a happy season, but the contract I was engaged with had me travelling with increasing frequency, I was becoming less of a remote worker and becoming more of a remote dad/husband.

Over the following two years, which basically brings us to today, I’ve had long periods where the work didn’t flow nearly so frequently as I’d have liked it to, and periods where I’ve spent far too much time pursuing various projects away from where we were as a family. I’ve settled into a couple great contracts at this point, and find myself with more room to breath and reflect on my life as a remote worker.

There are two questions I didn’t properly ask myself when I first began this journey as a remote worker. I’ll even confess that after two years, I’m only now just beginning to answer these questions in a meaningful way.

What am I hoping to gain as a remote worker?

What am I willing to give up in order to be a remote worker?

When I think about what I was (and still am) hoping to gain, it’s obvious enough to say freedom and autonomy are the top reasons most people (including myself) would choose to work remote. There are practical reasons too, many people work from their houses or villages to avoid the commute into a big city. Still, others do so because they long to have the concentration afforded by having no one other than your cat around to bug you.

For me, my wife and I wanted to bring our children to various cultures and cities so they might become enriched by the diversity, exposing them (and us) to the rich tapestry of people and ways of life. Also, how amazing is it to learn about Ancient Rome while exploring modern Rome?! I’ll also confess to a romanticised idea of sitting in cafes around Europe and writing world-changing policy documents and communications. But, I wasn’t yet willing to give up the regular opportunity to work directly–face to face–with co-workers and clients. I also wasn’t ready for the constant battle of trying to hobble together all the elements of a good work station. And so, even as we have been travelling as a family, I’ve continued to do additional travel by myself in order to network at various events, and have the opportunity to build relationships with clients, partners, and industry peers. If I’m honest, there’s also a healthy amount of FOMO (fear of missing out) involved, I just can’t imagine missing the safety meetup of the decade. What if there’s a potential client that I’d never have met if I wasn’t at that event which might require me to travel 6 hours on a train for a 2 hour meeting? And there’s that meeting in two days, makes sense just to stick around here for that event too, I’m already here, right? It’s this thought process which lead me to becoming more of a remote dad/husband.

In a statement of personal reflection, I gave up the wrong thing.

Deciding why you want to become a remote worker is for some a luxury. Many remote workers do so for reasons entirely more practical than for the freedom to travel or work from an ideal work space. For some, it’s not even a choice; perhaps they haven’t the ability to move to where the job is, or they have mobility issues which preclude them from the opportunity to co-locate with their colleagues. Perhaps this great gift of modern connected technology has given people more options to work with great companies, regardless of their circumstances. But, for those of us who are taking advantage of the perceived luxury of being able to work from anywhere, the question of why is more nuanced and ought to be given careful consideration. One ought to consider if their motivation to work remote is realistic given their means, their opportunity, and their ambition. One also ought to consider what they have to offer as a remote worker so they can avoid taking more than they give, whether it’s to the company that’s afforded them the opportunity and trust to work from a remote location, or the culture in which you visit.

But I think the question of what you’re willing to sacrifice is possibly an even more important question, and one that is super hard to answer when you’re on the cusp of making your what’s in my travel bag video.

Side note, there are over 180 million what’s in my bag videos…

Working remotely can be amazing! I have incredible memories of sitting at a seaside bar in the South of France, working away on my laptop in the warm spring sun while my kids play in the sand 10 meters away from me.

But I also have a lot of memories where I’ve stayed up for 1a for a meeting with someone on the Canadian west coast. Or wasting half my day looking for a cafe with WiFi. Or finding a cafe that will allow me to plug in my computer to charge it. Or, when I’m incredibly lucky, finding a cafe that has both WiFi and power outlets. If you’re freelancing, you often have to decide between taking that meeting with a potential client on the same day that you were going to hike the Alps, or miss going out to the pub with some friends you’ve met while travelling because there’s an opportunity to join a meeting that’s entirely focused on something that you want to advance in. Often, you find that you need to sacrifice the endless opportunities available to you, wherever you are, or an opportunity to advance your purpose and career (not to mention earning potential).

But, I paint a dim picture and I don’t intend to. For me, I’m learning that I have to sacrifice some of my career ambition if we’re to continue travelling. I have a couple excellent clients, and it’s enough to be working with them, and giving them my professional best. I want my children to remember being in the French Alps with me, not being in the French Alps while I was somewhere else.

When I ask myself the first question, what am I hoping to gain as a remote worker? The answer is clearer to me now, I want to further my understanding of various cultures and witness the changes (good and bad) to these cultures in this time of incredible and rapid change.

As to the question, what am I willing to give up in order to be a remote worker?Quick career advancement. This is actually a really hard one for me, not because I’m an insanely ambitious person, but because I have so many ideas for various companies, and how I’d lead those companies. But learning and gaining these experiences are better investments for me. As for my wife and children, I want to have this experience with them, and I want my kids to grow up understanding different cultures in a far richer way than they’ll be able to by watching YouTube videos or following interesting people on Instagram (although that too can be valuable). This is an investment in them!

My mother and I are doing a research project together, we’re looking at what makes remote workers successful, and we’re learning a lot of really valuable things (you should check her blog out). We just finished a trip through Europe where we visited several co-working spaces in Finland, The Netherlands, Germany, and England. One of the things that really stuck out to me, as we met with remote workers, is how loaded this designation is. One thing is clear though, work is changing, and for those of us doing the remote working thing, it would be wise of us to see ourselves as late pioneers. To be sure, there are people who have been working remotely for far longer than Yonder has been talking about it. But the reasons why people are working remote, and the sheer number of people doing it now has so dramatically increased that there is a ton of learning to be had right now. Some of us will do it well and bring incredibly valuable best-practices that will help the whole business community. Others of us will crash and burn, either because it wasn’t the right thing for us or because our managers/clients failed to provide the support and direction needed to be successful. This too is incredibly valuable. So, be observant and share what you’re learning along the way.

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.