What it’s really like to work as a nomadic developer

originally posted and edited via Scotch and the Fox

steelhead falls, near bend, oregon

Currently, I am technically homeless and my car is parked on a random island near Seattle.

For the past two years I’ve been working in San Diego as a Software Engineer at Turbotax. During that time I also worked part-time as a Ruby on Rails mentor for an online web development school called Bloc. This September I started to feel extreme wanderlust and was less-than-energetic about the work I was doing. I decided to quit my desk job and pursue mentoring with Bloc full-time remotely so I could solo-travel with no destination or end date in mind. What’s it really like to globetrot solo and be your own boss? Below are some things I’ve learned and experienced on my journey so far.

denali national forest, alaska

Will I like it?

To say the least, this time has really brought back my creative energy. It’s taken me a while to realize that I can create a life where I can code as many hours as I want and still make time for photography and other creative aspirations that make me happy.

Will I feel lonely, scared, or bored traveling alone?

100% opposite. My life is so far from routine; most of the time I feel like I’m on this weird energy high and have a hard time sleeping because I’m so excited. Adventure is happening at every minute and I don’t know who I’m going to meet or what I’m going to stumble into. As far as lonely goes, the biggest thing I’ve learned so far is that there are no strangers — just friends I haven’t met yet. I’m not someone who fears picking up conversation with strangers, so yes this has helped me so far, but truly most people aren’t out to kidnap you. Also pro-tip: if you ever start to feel homesick, check yourself into a cozy bed and breakfast. The warm and homie vibes that come from a home-cooked, communal table breakfast will get you right back on your feet.

talkeetna, alaska

Before I got to Alaska this year, I was looking through tagged images of Denali National Park on Instagram and found a couple profiles to follow that had cool adventure shots. I got to Anchorage and was driving along the Turnagain Arm and stopped to watch a few surfers. I saw one guy walk to his car and I opened my window and said “Oh my gosh you guys are surfing, what’s the temperature of the water?!” He responded and said “It’s about 40 degrees, not too bad, we have really thick wetsuits! You should come back and join us later!” I just laughed and went on my way. The next day I looked on Instagram and got a message from one of those accounts I followed saying, “Hey did that happen to be you who stopped to watch us surf the other day?” I ended meeting him and his friends while I was in Oregon (we both also happened to be traveling in Oregon after I left Alaska).

bend, oregon with him and his friends

Of course, there are downsides to this type of lifestyle.

Since what I’m doing is far from the norm, people often have a hard time understanding it or thinking any of it is real. Recently people have told me they would die to live this spontaneously. While I’m still having a blast, I’ll be real with you: it’s alittle overwhelming. When given this amount of freedom and choice of what one can do at literally any moment, it’s not always like Homeward Bound. The amount of decisions I have to make on a daily basis can sometimes leave me numb and unproductive. My questions vary from: ‘can I park my car here for two weeks overnight without getting towed?’ to ‘will this spray protect me from a bear, a moose and a mountain lion?’ Also, there are a lot of logistics that go behind planning my trips that make it hard for me to stay present while I’m on the trip itself. Tip: I don’t like hiking alone so when I get to a new town I find outdoor enthusiast groups to join on meetup.com.

beaver creek, colorado

Lastly, another emotion I’m feeling is that I’m embarrassed by how lucky I am to be a nomadic developer. I often hear my brain say, ‘This is not real life. You’re too young to enjoy this, nor have you paid any major dues to deserve this flexible lifestyle.’ It’s easy for me to forget that this wasn’t just luck and it didn’t happen overnight. I’ve taken a lot of risks and have had a lot of challenging experiences, but I keep putting myself out there. But with all that said, the emotion is real, and I’ll admit it slows me down and distracts me from living in the moment.

driving through alaska

Alrighty, That’s it for now. As of today I’m taking a little break from traveling full-time and my home base will be Minneapolis (where I’m from). I’m still mentoring for Bloc, producing unplugged retreats, and collaborating with artists on random things. If you want to meet for coffee or collaborate on something, ping me on twitter @bobbilee19

⋐ engineer and evangelist @square | running unplugged outdoorsy retreats for people i look up to @railscamp_usa + @lodgedout ⋑

⋐ engineer and evangelist @square | running unplugged outdoorsy retreats for people i look up to @railscamp_usa + @lodgedout ⋑