New Worker Mag » Digital Nomads » On being a remote CEO

by Karoli Hindriks

I’m the kind of person who believes in the magical life-enhancing properties of travel. Whether it’s for business or pleasure, traveling encourages the movement of ideas and helps us all see the world from new perspectives. That mission—spreading ideas and innovation beyond borders—is what I’m working on with Jobbatical, the global hiring platform I co-founded a bit more than two years ago.

My most hardcore travel extravaganza of recent years—or perhaps of all time—happened in September 2016, when over a one-month period my travel trajectory went like this: Estonia-Singapore-Malaysia-Singapore-Malaysia-Australia-Malaysia-Japan-Malaysia-Singapore-Estonia. What looks like a serious accident with a typewriter is, in fact, just par for the course when you’re the founder of a startup with global reach.

My most recent absence from the Jobbatical office was also precisely one month long. Enough time, apparently, for my desk to be reassigned to a new team member. Now I’m a digital nomad in my own office, with no desk to call home. It’s a small price to pay for the privilege of getting to see so much of the world—and there are plenty of comfy beanbags to choose from (as required by startup law), so my loss isn’t that great.

Over the course of that fateful month, I did my work from the USA, Costa Rica, Panama, and the USA again. For me, working on the go is the new normal. We humans tend to get used to situations pretty easily if they repeat often enough. As soon as I open my computer or my smartphone, it’s like I’m entering my office virtually. In many ways, it doesn’t feel that different from being in the same room with the rest of the team.

In reality, of course, working remotely requires a different structure of communication and I’m still learning how to be present for the team even when I’m on the other side of the planet. Our team as a whole has learned countless lessons over the past year. Getting a constantly growing startup team to work as a unit when people are distributed all across the globe has been the learning experience of a lifetime. Managing expectations, wrangling time zones, and keeping communication flowing freely—all the while remembering that people are just people, wherever they are—is a balancing act for all of us. With the use of tools like Slack, Asana, Timetastic, and the art of common sense, I think we’re getting close to uncovering the secrets of efficient remote work.

To stay connected while I’m away, I like to carry my team in my pocket (in smartphone form) and share snippets of my travel experiences. In Costa Rica, while I was interviewing a senior sales candidate for Jobbatical via video call, I suddenly spotted a huge iguana. I cut our discussion off, ran to the iguana and showed my interviewee the tiny monster via our video call. Team Jobbatical knows me well enough not to be surprised when this sort of thing happens. They’ve all seen footage of me being chased by monkeys on a morning run in Malaysia. In the same vein, my regular announcements of “I almost missed my flight because this crazy thing happened” don’t even raise an eyebrow anymore. But the candidate was rendered quite speechless by my little adventure with the iguana.

I’m not afraid to declare that I love the world and its creatures in all their weirdness, and I believe that sharing such moments of genuine emotion helps shape a culture of openness. And beyond that, it’s just fun!

It’s not just the work aspect of remote work that can be challenging. I myself am lucky enough to be highly adaptable to time differences, and my 4-year-old is also already a master of traveling, having accompanied me on so many of these trips. My personal struggle is the fact that I have Restless Legs Syndrome, which becomes quite torturous on long flights. That’s one reason I’m crazy about collecting frequent flyer miles and bargaining possible upgrades to Business Class (for the bed). Another thing I’ve found is it is essential to be well prepared for in frequent flying are the effects it has on your skin. On long flights, I always have to wear the most moisturizing face masks, even if it means my fellow passengers see me as the lady with the scary face for the rest of the flight.

On balance, it’s obvious that these are minor inconveniences. What’s a patch of dry skin compared to the extraordinary privilege of being able to build and lead a startup team from the lush jungles of Costa Rica? What could be more rewarding and eye-opening than meeting clients from NYC to Singapore, hearing their stories, and working with them to build a more open world? Restless legs or not, I can’t think of anything I would rather do with my life.