The Traveling Businessman: How I Spent 5 Months Running My Business on the Road. (Part 4 of 3)

The Traveling Businessman: How I Spent 5 Months Running My Business on the Road. (Part 4 of 3)


Check out Part I if you missed it.

Check out Part II if you missed it.

Check out Part III if you missed it.

On the Road Without a Home

Feeling frustrated with our last stay, we packed up our car and headed east. Because we left so quickly, we never even had time to plan our next destination. It was a little nerve-racking. Up until now, we planned 30-day stays at each location. Now we were faced with a weird two-week window between leaving Pennsylvania and when our next stay was booked on Cape Cod.

The logical thing to do was to try and contact our next Airbnb host and see if they had an early opening for us. As we pulled away from the cabin, my wife started making phone calls.

After several unsuccessful voicemails and emails, we decided we needed a "plan C". We found a hotel a few miles into New York state and stayed the night. We had a much needed nights rest and started our journey again in the morning. Still waiting to hear from our next host, unsure of where we were going, we kept on our path toward Cape Cod. If we didn't hear from our host soon, we'd have to bite the bullet and pay the full price for a two-week stay somewhere else.

As we continued down the freeway, we received a phone call from an unknown number. Luckily for us, it was our host in Cape Cod! We told him our situation and he was more than happy to accommodate. He told us the code to get into the house and we were all set.

Cape Cod, Massachusettes

Later that day, we pulled into what would turn out to be our favorite Airbnb of the entire trip. It was a small beach house with a gravel driveway. There was a grill in the backyard and an outdoor shower for rinsing off after the beach.

My "office" ended up on the kitchen table, which was mostly in the way the entire time. Unfortunately, there wasn't another surface anywhere in the house I could use as a desk.

Our time in Cape Cod was both relaxing and busy. I had several large animation projects I was working on that took up a lot my time. Not so much so, I couldn't still explore the Cape with my family.

Cape Cod is full of little beach towns all along its coast. The small town we were living in was Dennis, MA. We were there right at the end of the season. Once Columbus Day hit, a lot of the touristy places started shutting down. It ended up being us and the retirees left. We spent a lot of time walking the mile stroll down to the beach. We saw several incredible sunsets and played in the warm sand.

Halloween happened while we were in Massachusettes, so naturally, we drove up to spend it in Salem. This was my wife and my second time spending Halloween in Salem. They whole town decorates for Halloween. Needless to say, it's a pretty big deal there. There are witches reading palms and a reenactment of the Salem witch trials. It's a good time.

Our theme for our costumes was "wanderers." I dressed up as Waldo, my wife was Carmen San Diego, and my daughter was a very adorable Amelia Earhart. I spent the night feeling like a celebrity. For some reason, the Waldo costume was a huge hit. I had people running up to me all night asking for pictures. Yelling "I found you!" at me as they walked by. It was hilarious.

We explored everything the Cape had to offer. We even ventured off the Cape several times. We saw Plymouth Rock (one of the biggest disappointments of the entire trip—see photo below), spent a few days in Boston, and ate a lot of Lobster.

Homeward Bound

We decided while we were on the Cape, it was going to be our last major stop before heading home. We felt pretty satisfied with the time we spent on the road and all of the amazing things we had seen and done.

It's amazing how easy it was to keep my business going no matter where I was. We had a couple of small struggles to work through on the way, but for the most part, it was smooth sailing. I could meet with clients and coordinate work with my team from anywhere. It was a wonderful realization and completely freeing.

Despite the fact we were on the road for several months, we still managed to see our family and friends. We started our trip with a month at our Aunt and Uncle’s home in Austin; we eased into our adventure while still surrounded by the comfort of family. My in-laws flew out to visit us in Washington, D.C. for a few days. We were able to spend time with our friends, Dan and Sarah, at their amazing home in Virginia. We even had long overdue reunion with old friends in Baltimore where I tried blue crab for the first time. It’s always nice to see a familiar face when you’re away from home for so long.

The Journey Home

As we began planning our drive home, I wanted to squeeze in a few more stops along the way. Things I knew I would never do unless I was already in the area. The top two stops I wanted to make was Niagara Falls and Mt. Rushmore. I knew if we didn't stop then, we probably never would.

The day finally came to pack up all of our belongings for the last time and start heading west towards home. The total drive time was about 35 hours. Ouch.

I've always been the type of person that likes to get in the car and get to where we're going. No need to make a long trip even longer. So as we got close to our first planned stop at Niagara Falls, it was admittedly difficult to stop. We arrived at night, so stopping to see the Falls would mean we'd need to get a hotel and see them in the morning. We had only been driving for 8 hours (small potatoes after driving all over the country), so we decided to catch them next time we visit Toronto. From what we hear, the Canadian side is better anyway.

We ended up driving through the night. We drove about 22 hours before stopping in Omaha, Nebraska. We booked a room in a really nice hotel and ended up getting a free room upgrade because we tried checking in too early. Score!

The next day, we woke up and hit the road. Still a little exhausted from the long haul from the day before, we considered how much we really wanted to see Mt. Rushmore. It would add about three extra hours to our trip...Rushmore was out. We wanted to get home.

Home Sweet Home

About 15 hours later, we pulled into the driveway of our house. We made it.

I look back now and I can't believe we were gone so long. It was surreal. The business was doing great. My family enjoyed the experience. My daughter has already seen more of the world than I ever did at her age. It was on this trip she learned to walk. I know she probably won't remember it, but at least we have pictures.

Would I do it again? Probably. Would my wife? Probably not for quite as long. Now that we've been home for several months, we've been considering where we would go next. The West Coast is definitely an option for a bit of a shorter trip. Other than that, our next trip might need to be international.