How (and why) we decided to spend our lives traveling

Choosing to uproot your entire life isn't a small decision. Here's why we did it

In 2015 I led pretty comfortable life. I had recently moved from a house I rented in Boulder right off the Pearl Street Mall. It was just a few blocks from where I worked as a startup cofounder, and I hardly ever left town in the year I lived there. Boulder isn’t terrible, but it’s small, and I felt penned in.

Now I lived in downtown Denver. The new commute to the office was, surprisingly, a complete non-issue. I would get on the bus a few blocks from home, and get off a few blocks from the office. The entire ride I could read or attach my laptop to my phone’s hotspot and crank out some work. The buses ran every ten minutes, so there was no wait, and no frustration.

The new Denver apartment was great. Decent view, great location. Lots of bars and restaurants within walking distance, and the central transit station opens up your dining choices to the whole metro area. The apartment itself was brand new, so no more struggles with air conditioning, or leaking ceilings, or expensive utilities. No Boulder bullshit about composting. I had a few neighbor-noise issues, but nothing compared to being near Pearl Street Mall. Soon we were in an almost luxurious routine, every evening involving either my girlfriend’s excellent cooking and and my homemade cocktails, or us exploring a new restaurant and new cuisine.

In my career as well, I was comfortable. I was an executive at a well-funded startup that was finding its market fit, growing both in revenue and in personnel. I no longer found myself awake at two am running over arguments in my head, stuck in the rehearsal loop of what I should say or should have said when arguing with a cofounder. The years of stress associated with late-night product issues were finally behind us, and we’d built a strong engineering team I could trust.

My personal life had also reached a great place. Since divorcing years ago I had been hopping around from relationship to relationship, a serial monogamist. If I spent more than a few months with someone it was more a matter of laziness and companionship rather than any connection or love. In mid-2015, however, I had met a wonderful woman who changed that. She was smart, and driven, and beautiful, and made me realize I didn’t need to settle. We spent all of our time together, fell into a passionate and caring relationship, and moved in together. There’s something so foundational in your life when you have someone that cares about you, and that you care about and can depend on.

So why overturn this nice, easy lifestyle? Why subject ourselves to uncertainty and discomfort by taking on the ‘digital nomad’ lifestyle? I’ve never been happier with how my life was going, so why shake it all up now?


Now, I’m not spewing the cliche “we’re becoming digital nomads to get away from it all” or whatever. No, the answer to “why now?” is that I finally have freedom and flexibility in all the aspects in my life that would hold us back from living the way we want.

Financially, we can make this work. It’s not that we have fat stacks and don’t need to work – I’m not the ‘not working’ type anyway – but rather that I can work remotely and sell my time and skills. Also, the technology and industry is only recently to a point where that’s possible and (somewhat) accepted.

Careerwise, the startup had reached a point where the technology could stand on its own and wasn’t holding the company back. The focus of the company had moved from the technology to scaling the marketing and sales. I had spent four years there, so my vesting was complete and I’d never own more of the company than I do now. That made it time to diversify anyway.

Logistically, there’s not a home to be sold, or a car payment to make, or student loans to pay. Not that there’s not a lot of things to take care of but I lead a far less entangled life than most people, and I can more easily uproot everything.

What’s more, this freedom is transient. It’s not long before we’ll want to have a family and settle down. While children don’t make it exactly impossible to live nomadically, they do make it difficult. Some things become reckless or impractical, like staying on a live-aboard for diving. Some things are just less ideal, like moving an infant around on a bus in Ecuador.

The sweet spot in my career is fleeting too. I’m fine and happy to do consulting and freelancing for a few years as I start to pull together ideas for the next startup. But when it comes time to throw myself into the next venture, I’ll want and need to be in a more stable and predictable routine again.

This is the time for us to live precariously. To embrace that not everything has to be simple and comfortable. To get comfortable being uncomfortable. To drink in those life experiences you can’t get while living the domesticated existence. To experience travel and new cultures and new foods and lifestyles.

The time is fleeting.