How and Why I Became a Nomad
Over the last 30 days, I’ve sold or left behind most of my possessions, put the essentials of my life into a backpack and a carryon suitcase, and moved 5,000 miles away to Berlin. I’ll be here for the next 60–90 days. After that, I have no idea where I will go.

Five years ago, I moved to Tampa, FL from NYC. Before that, I’d lived in Scotland, Philadelphia, and Pittsburgh.
I’m the first to admit, I’ve long sought out geographical changes to solve my problems. But, for the first time in my life, I don’t feel like I’m waiting for something to happen.
I’m simply here. This is the story of how it came to be:
In high school, I couldn’t wait to get to college. In college, I couldn’t wait to get a job. Once I had a job, I couldn’t wait to start my own company. And once I started my own company, I couldn’t wait for it to explode and change the world. The more waiting I did, the more I realized how unhealthy waiting was, and I could never quite figure out how to break that cycle.
I’ve spent most of the last year working to exit WeVue, a company I’d started with a few others nearly 5 years ago that brought me to Tampa.
With a team I love, we built something I was proud of, but for a myriad of reasons I won’t go into, it was time to marry our project with a larger organization, to give it new leadership and support beyond what our team was capable of doing.
That transition took 6 months. It was an odd state of limbo: one where for the first time in as long as I can remember, I wasn’t working towards building something.
I had that time to examine my life and to look at what I wanted my future to be like. At first, my thought was that I needed to go hop on the corporate bus.
So like any good job seeker, I began blasting out applications. I redid my portfolio. I reached out to anyone who was anyone that might have a lead for me on an interesting company. I read the Cracking the Product Manager’s Interview. I spoke to people at Google, Facebook, 5 person startups, agencies, and unicorns.
The more I spoke to people about what I should be doing with my life, the more I realized that no one can tell me what I should do. For every opinion on how my career should go, there’s a counter argument that looks just as valid, and ultimately I knew I was in the midst of choosing my own destiny.
The more I interviewed, the less excited I’d get. One opportunity would pop up, the process would go well, and I’d be convinced that was the perfect job for me…and then I wouldn’t get an offer.
And through that cycle of interviews, rejections, and follow up calls, I was continually questioning myself:
Is this my dream?
For years, I’d tried to convince myself that it was. I came to see that there were two paths in this world for the types of art and design I practiced: I could slave away for years in a shit box apartment creating my own work hoping that some day I’d be “discovered”, or I could go and figure out how the internet works and try to build a company.
While living in New York, I felt like everyone I met was a starving artist who actually just worked at a hipster coffee shop. In LA, everyone is an actor that only just goes to auditions when they can get a break from serving tacos at some Mexican dive bar.
Meanwhile, in places like San Francisco and Lower Manhattan — young people create things that drove the world. They build companies and fortunes where art and design played an integral role. Didn’t that sound more appealing than trying to write a script someone would Netflix and chill to once and forget about the next day?
I came to believe that these boxes I was seeing were really boxes of my own making.
Those people serving coffee and tacos and running off to auditions were often times chasing a dream that I was running from.
The world provides us with shapes and shades and we fill them in ourselves — those stories we tell ourselves, the boxes we think confine our existence are never real. Yet, oftentimes the world conspires to convince us that the box is all there is so that we can sell ourselves on living a life we don’t really want to live.
Had I been doing that all along?
In the midst of all that questioning, I found myself sitting across the table from two guys wearing flip flops at a Capital Grill in Naples being sold on the idea of working for their small but growing marketing firm.
“You guys don’t care that I’m not in Naples,” I asked.
“We’re just happy you’re in Florida,” they said.
“What if I wasn’t in Florida?”
“If you go to China, just send us pictures.”
“So what’s your vision, what’s your mission?” I questioned.
“Honestly, it’s pretty simple. We don’t want to build some massive company. We want to be behind the scenes. We want to spend more time swimming with our kids. We want to fish. And we want to pay for that by helping our clients,” they replied.
Damn…that sounds nice. After spending half a decade surrounded by people building widgets that would change the world, to hear that type of honesty and see an ambition that was not about conquering something but building a life that was worth living for the sake of living sounded like what I’d been looking for all along.
After that meeting, I went to Russia.
Random, I know, but a friend of mine was getting married in Siberia…and one only gets asked to be a groomsman in so many Siberian weddings.
It was there that I realized how much I wanted to be physically moving through the world. I’d tried to sell myself on the idea of living in one place, building up a network and contributing to a community. And while I’m still convinced that has a merit and value, I don’t own anything, I’m not married, I don’t have any kids, and I have this insane itch to see the world and experience all that is has to offer. It was on that trip that I came to realize that perhaps I could make working and traveling my focus for the near future…
When I returned, the guys who want to fish and swim offered me a part time job that would pay me enough to basically live and work abroad. I’d have enough time to work on my own projects or take on other freelancing gigs (Hey! Hire me :)
Defining My Fears
That night, as I pondered the next step in my life, I stumbled upon Tim Ferris’s recent Ted talk on “fear setting”. It’s an exercise that can be done in less than an hour, and it asks you a series of questions related to some big decision you’re making with the goal of getting to the root of your fears. I came to see that, while I had this innate desire to go live a nomadic lifestyle, one by design outside of the confines of what a traditional 9–5 looks like, I was deeply afraid of what that could mean.
Was I giving up on building a company? Was I letting other people down that had expectations for me, most of which I’d made up in the first place? Would I fail miserably, get sick, lose all my money, and be forced to return home in shame. If that happened, would it be that hard to recover from? With enough digging, I came to realize that if I didn’t go — I’d always wonder what life could have looked like if I did.
If I didn’t take the corporate job, I knew I wouldn’t be sitting here thinking about “well, what could my life have looked like working 60 hours a week trying to build someone else’s dream and pretending it was my own?”
While ego can be a harsh mistress, Mr. Ferris also asks you in his exercise if there are people doing what you want to do successfully. “Are they smarter than you?” he asks. Today, hundreds of thousands of people live and work remotely, they travel the world successfully, and I knew I was capable of becoming one of them.
So I took the job and booked a 1 way flight to Berlin that afternoon.
Over the next two weeks, I watched way too many reviews on which backpacks were appropriate to travel the world. I sold my car, gave away most of my clothes, and put the rest in storage. Now I’m sitting a block from Boxhägner Platz, and I’m about to hop on the U-Bahn (subway), head to Schöneberg, and have coffee with some random dude from Portland.
I couldn’t tell you what I’m going to do tomorrow, and that is terrifyingly awesome.
