What's It Really Like To Work As A Nomadic Developer?

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.

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.

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). And yes, we are still talking :)

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 a little 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.

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. 

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: web: www.bobbileehartman.com twitter: @bobbilee19 instagram: @bawbelee

Leaning In/Tipping Over

I leaned in and fell over.

Here's the thing. I work. A lot. I just do. I always have. Because I liked shopping. Because I like good food and good wine. Because I dislike crowds, getting beer spilled on a new outfit and also, because I was a great sober cab for my friends in college. Afterall, safety first! 

So when "leaning in" became a career verb, I put on my Bossypants, said, "Yes, Please!" and took every opportunity to hustle like a Girlboss. Can you blame me? Each of those books tells you to work your tail off, if you want to basically be a badass like any of their authors. What I failed to realize is that those books are condensed career lifetimes. As in, I can't make my entire 2015 about checking every single career to-do off of my list.

At this exact minute in time, I find myself working for no less than 6 businesses/people. Six. And yes, I have as many hours in the day as Beyonce, but she also probably has a personal chef and someone to do her laundry and her hair. I did not wake up looking like this. I woke up puffy, frizzy and needed to brew my own tea, and had to put on my pants two legs at a time because I spent too much time catching up on Instagram this morning.


I didn't realize there was an International Women's Day this month until the reality of my many careers had already sunk into my bones and I skimmed my emails. I quickly found that these women who work hard to be recognized as equals among their male counterparts are seeking quality, not quantity (although technically equal pay would be quantity but I beg to push for the quality of life you can lead as a result of that quantity.)

When I weighed my many tasks against the level of quality work I'd be able to contribute to each outlet, I realized I was spreading myself thin. Too thin. I was dropping the ball on things that actually mattered to me for petty opportunities that I "could" or "might" pursue. I look at those words with the same disdain I do a sweater that I think I *might* be able to unshrink. 

For all of you out there working hard, I hope you are working for what matters to you-- not because you think you should, but because you know in your bones that this-- whatever "this" happens to be--is worth it to you. 

I leaned in, and tipped over from the weight of my world hurting my shoulders. I don't need to do it all right now. I've picked myself right back up, decided what's realistic about my time, and what deserves my energy. These "women's days" are more than just blasting Spice Girls  jams (although that doesn't hurt) and negotiating for your raise, it's also about making your workday meaningful. I hope for all the liberty we've gained, we continue to be mindful of self care--because I'll tell ya what I want, what I really, really want...I wanna, I wanna, I wanna...present the best version of myself--and my work--to the world and it's difficult to do that if you're juggling knives.