The Traveling Businessman: How I Spent 5 Months Running My Business on the Road. (Part 2 of 3)

The Traveling Businessman: How I Spent 5 Months Running My Business on the Road. (Part 2 of 3)

Part 2 of 3

Check out Part 1 if you missed it.

Too Comfortable

We live our lives too comfortably. We have our daily routines. We collect our stuff. We like things the way they are and when change comes, it makes us cringe. We long for the time spent working, watching Netflix, doing things for our kids, then going to bed. Then we wake up the next day and do it all over again.

We like the occasional week or two of vacation and talk about how we wish we had more time to travel but what do we do about it? Work. Kids. Netflix. Sleep.


For most of my life, I’ve know I would be independent and self-employed. I didn’t know how but I always considered myself to be somewhat unemployable. I always wanted to move up faster than I was ever allowed. I've never enjoyed doing work only to help other people achieve their dreams of being successful. When I was 19 years old, my boss told me I had a problem with authority. I was offended at the time, but as I got older, I realized what he said was kind of true. I have a hard time listening to people who don't have proven experience.

All this leads to 2013. I moved to Austin, TX. Just me and my St. Bernard, Mac. I moved to work at Apple with their Pro App support team. I was happy to be there and even happier to discover Austin. I had no idea what an amazing city Austin was. Anyone from Austin will resent me for spreading good things about it, though. It’s getting pretty overcrowded there.

Time to Take the Leap

I decided while I was in Austin, it was now or never. It was time to make the jump. Startups and entrepreneurs were everywhere. If I was ever going to ever start my own business, it was going to be now. I gave my two weeks at Apple and cashed out my 401K. I decided to start music collaboration website with my friend, Brian, called Sound Drop. Something I'd been toying around with for several years.

Long story short, Sound Drop (renamed ryffed) ended up failing and I moved back to Salt Lake City with my wife. I believe Sound Drop failed for several reasons: bad marketing, poor execution, money, impatience, and an overall lack of interest. It was a hard pill to swallow but looking back, it couldn’t have worked out better. While creating Sound Drop, I needed a video on the home page to give people an idea of what our service was all about. We didn’t have money to hire anyone, so I decided to learn After Effects, and I loved it.

When I finally pulled the plug on Sound Drop, I looked back to try and figure out what I learned. I wanted to feel like my entire experience wasn’t wasted. As I began thinking about it, I thought back to the time spent making my video. I remembered how much I loved making it—I’m happiest when I get to be creative. I decided to take my video and look for other companies in need of a similar product. I ended up finding a production company looking for exactly what I was making.

Since then, I have grown my portfolio and have worked for companies all over the US and the UK. I make videos for tech companies, healthcare companies, and everything in between.

I edit and animate explainer videos and am lucky enough to do it all from my own home. I get to spend more time watching my daughter grow up and learn new things. I get more time to do the things I want to do.

I Created a Job for Myself

Three years into it, work was good. I was busy. It took a while to get a good routine going. Working from home comes with its own challenges most people don’t see. Once my routine was set, I began to feel almost like I was working for someone else. My days were scheduled for me and I couldn’t take a day off whenever I needed. I know this sounds petty, but you become self-employed for the perks and freedoms that come along with it. You also give up some of the luxuries of having an employer. For example, cheaper healthcare, 401K, paid holidays, “security,” etc.

This got me thinking. What else am I not taking advantage of while being self-employed? What happened to my freedom? I work from home, which means I could work from anywhere. Why wasn’t I taking advantage of this? And so the idea for an open-ended road trip was born.

We didn’t exactly know how long we were going to be gone. What if a month into it, we start regretting everything and come running back home? Or maybe we’ll fall in love with the nomad life and never have a permanent address again. We weren’t sure so we thought it best to take it one month at a time. We’ll spend one month in each location so we can unpack our stuff, and settle into the new city. We could enjoy our time there without feeling the rush to do and see everything in a short amount of time.

Time to Go

So July 1, 2016, came. We packed only what would fit into our car, strapped our baby girl into her car seat, said a little prayer to the road trip gods, and left our home in Salt Lake City. Our first stop was Austin, TX. We moved away from Austin about two years prior. We found ourselves missing the delicious queso and kolaches that were flowing abundantly from the Lone Star state.

The animation work I do requires a lot of computer screen space. So I work mostly on a monster 27" iMac. This makes the whole dream of sitting on the beach doing work on my laptop not all that feasible. Although some people can make it work.

The drive from Salt Lake City to Austin is about 22 hours. In the past, I've made the journey on my own without stopping. As I near 30, I've found it to be a little more difficult than it once was. There isn't quite enough coffee to keep me going. I made my wife think I was stopping halfway for her, but it was mostly for me. Don't tell her.

We set up shop in a hotel room in Albuquerque, NM. I used the horribly slow internet (didn't think that part through) so I could download some client assets. It was so slow, I had to let it sit all night just to download a gig of video. After choking down the free continental breakfast the next morning, I got a few work things done and then we hit the road again.

Throughout the entire road trip, I tried to schedule video projects in between travel days. This didn't always work out and ended up with us having to break out the laptop and spend a couple hours working in a Starbucks in some random town (also painfully slow internet).

Finally Made It!

Several baby breaks later, we made it to Austin. My wife's aunt lives in North Austin and happened to be traveling the same time we were going to be there. She was kind enough to let us stay in her home for the month of July. I set up my office and started work again. Aside from being in a new time zone, it was just like I was home. As far as my clients knew, nothing had changed. Success.

During our time in Austin, we hit up all our old favorite spots. We sucked down what must've been several gallons of queso and hundreds of tacos. Maybe a bit of an exaggeration, but my pants were definitely tighter by the time we left. Mmmmmm....queso.

Austin is one of my favorite places. There are always things going on there. Everything from ice cream festivals to Bastille Day celebrations to Chicken Shit Bingo (look it up). The music and food are always spot on. We were on the move quite a bit and ended up getting a little burned out. Lesson learned: take it slow.

Did We Make a Mistake?

A couple weeks into our stay in Austin, we started looking into where we wanted to go next. This was when we started getting cold feet. We knew Austin well because we spent two years living there. It was still pretty comfortable to us. Now as we planned our next stop, it was going to be completely new. We were going to venture off into the unknown. We could go anywhere, but where would we go? Are we sure we really wanted to keep going? It would certainly be easier to just head home after the month was up.

We sucked it up and decided to press on. Our daughter was happy. Work was good. So we booked our next place. Washington, D.C.


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