The Traveling Businessman: How I spent 5 months running my business on the road. (Part 1 of 3)

The Traveling Businessman: How I Spent 5 Months Running My Business on the Road. (Part 1 of 3)

Part 1 of 3

"Your time is limited, so don't waste it living someone else's life." –Steve Jobs

On July 1, 2016, we began our journey. I packed my family into our SUV and we began a road trip that ended up lasting almost 5 months. It was a life changing adventure. Luckily for me, I am able to run my business from anywhere.

For unknown reasons, I failed to ever make the connection between starting a business and personal freedom. I knew it existed but for some reason, I never felt like it was for me. Most likely it's because running a business is extremely stressful and time-consuming. Especially with a family.

It's Fun to Do the Impossible

Several years into my business my wife and I decided it was time to have a baby. I have always strongly believed when you have a baby, that child should become part of your life instead of the other way around. People stop being themselves when they become parents and forget who they are. We pretend it's the noble thing to do but in reality, it leads to midlife crises and children who grow up thinking the world revolves around them. Because of this mindset, we were able to take our 5-month-old baby on the trip of a lifetime.

When we first had the idea to travel around the country, we had the intention of purchasing a travel trailer. It could double as a hotel and traveling office. One RV trade show later—and the sad realization our SUV was really a CUV (crossover) incapable of towing even the smallest of trailers—we knew our original plan wasn't going to work. Not without a lot more effort and money than we were willing to spend.

Do What You Love and Love What You Do

Since first reading it, the Steve Jobs quote above has always been in my mind. I think about it when I am feeling stuck. It makes me look at my life and make sure I am living the way I want to live and not the way others think I should be living. It's why I am the way I am. It's why when others told us our trip sounded crazy and how it was fate the trailer didn't work out, we turned to a little website called Airbnb.

It was perfect. Airbnb's are everywhere. We could rent out homes along the way. The best thing was, they offered steep discounts if we booked 30+ days in a single location. Sometimes up to 50% off. Although we didn't know how long we were going to be on the road, we did know we wanted to "settle" into each place we visited. We wanted to feel more like locals than tourists. We knew if we only spent a few days or a week in each place, we would be in constant "vacation-mode" and quickly burn out. It's nice to be on vacation, but it's also nice to come home from one.

Where to Start?

It's a pretty big ordeal to plan a trip without an end date. We thought it would be best to decide all the places we would like to see while we were gone. We found an amazing app called Roadtrippers we used to plan out our trip. I highly recommend it if you're looking for a more adventurous road trip. We listed out all the places we wanted to visit and planned the best route to take.

Our first stop was to a city we once called home: Austin, TX.

Check out part 2 here