That time I quit my job and moved to Iceland


Well, not moved to Iceland, exactly. But three weeks ago, after three and a half years of loyal labor, I did give notice at my job. And tomorrow, I fly to Iceland for what was, when I originally booked the tickets, an indefinite period of time. And I loved that it was indefinite. I fear predictability. The root causes for this uprooting adventure include boredom, a short, muted daily crisis concerning the meaning of life, an inspiring girlfriend, and delusions of grandeur, but I think that those root causes soak daily in the fertile soil of my dread of habit and of the commonplace. Here’s how that fear became a single stuffed backpack and a plane ticket- and that restlessness became an abrupt left turn off the beaten path.

In college, I began work as a developer for a company that makes (fantastic) custom-embroidered and printed apparel and accessories. It was a desk job. It paid alright, provided security, and I was always improving as a developer, learning from the amazingly talented programmer that was my boss, Fabrizio (he’s (very) Italian). I graduated college, had a two-year run as the keys player for a great band (still holding my job), and when that band broke up, my stress levels finally normalized and I settled into work as my main priority. At that point, more than ever, every Monday, Tuesday, Wednesday, Thursday, and Friday, my life became very routine. The job itself was comfortable, but felt like a dead end. It made me impatient. I grew anxious; I began to look for ways to get out. I sought out another music project, hoping to build up a small fanbase and begin touring. I applied for other jobs. I sat at my desk and watched cargo trains pass on the tracks near the office and fantasized about hopping on one and heading off into sweet uncertainty.

I met my now-girlfriend Melissa at the company when she joined the marketing team. We connected over shared dreams of travel and aspirations of creative fulfillment – her in writing, myself in music. Our friendship was strained by our obvious chemistry. When the time was right, the  friendship broke, and we began dating.

She revealed to me early on that she had always wanted to go to Iceland. You can ask her why. But, initially, traveling there was this sort of distant possibility, discussed almost like kids might discuss going on road trips when they finally turn sixteen and get their licenses. There was this inexplicable wall between the possibility of doing this and the decision to do it. Until one day, for Melissa, there wasn’t. Her ballooning dreams of that adventure, all the things she read about Iceland, the videos she watched of its beautiful landscapes, her ego soaking up “you can do it” from everywhere from Pinterest to Rand Fishkin’s blog – all these things finally reached the edges of her mind, pushed up against that withering wall between “someday” and “right now”, and cracked through.

She put her first foot on the path to Iceland in an ingeniously simple way. She drew up a letter expressing her desire to travel there, as well as detailing her talents and capabilities, and sent it off. To whom? Everyone. Any connection she’d ever made, assorted companies she wanted to work with, Icelanders. And people responded. People wanted to help. Eventually, she had a breakthrough, when one amazing tour company, Icelandic Excursions, decided to give her the adventure of a lifetime in Iceland, on the house. In exchange, Melissa would promote and describe the adventures on her blog.

She was set. She would go to Iceland and support herself through her writing – a dream come true. What about me? I stood on the other side of that now-crumbled wall, invited, tempted, but unsure. I had three options. I could stay in Wilmington, NC, and continue to work my desk job.  Or, fueled by a competitive spirit, I could take a dramatic leap of faith in the direction my own uncertain dreams. Or finally, I could attempt to get a telecommuting position, and work as I traveled with her (and perhaps occasionally departing on my own). I could share the adventure, embrace the unknown, and eventually arrive back in the U.S., a world-traveled man, inspired, and with any luck, focused- ready to set foot down the path toward my own great accomplishments.

There really was no decision to make. I was coming to Iceland, too.

We booked one-way tickets. We would spend a month in Iceland, and then hop over to Europe, adventuring however we felt fit. We gave our three weeks’ notices. And tomorrow, friends, we board a plane, across the Atlantic, and into an entirely new adventure. Tomorrow is the end of routine, the end of certainty. I have no idea what tomorrow will bring, and I have never been more excited for that.

Keep up with the adventure at : the latest posts on our travels, collected from both of our blogs.

And, follow me on twitter @imoutofcontext .