5 Months On The Road: Lessons Learned

October 18th, 2014

Traveling, being your own boss, deciding what to do day by day without planning, all of these things do not come for free. Freedom has a price.

I always remind people that this type of nomadic lifestyle is not all paradise. It involves compromises. Here’s a few examples:

Connections with friends and family

We have made efforts to go visit old friends that moved away in several places around the country. It’s been great to see them. At the same time we wish we could have spent more time with them, making a Saturday night out every weekend. But people are busy, have schedules that do not match ours and we want to see other places as well. So the connection is brief, and sooner than you know we are back onto the next destination.

As the Thanksgiving holiday is approaching we are reminded that this will be one of the first years that we will not spend it close to our family. It’s a sad thought, but we’ll try to make the best out of it (we always try to).


Although it’s slowly changing, many people are not comfortable hiring someone who is constantly moving. As a user on Twitter pointed out, “this lifestyle cannot look good on a resume”. The statement is true in many aspects. You will unlikely land a normal job while being on the road. You have to be your own boss, find your own clients, sell your own services. You are also restricted in what type of jobs you can do. Road construction is not something you can take with you on a trip. Software development, accounting, writing, design, translating tend to work much better. An independent type of work brings in income fluctuations that are not digestible for everyone. As a long time poker player, I don’t mind financial fluctuations. But I can see how it could be worrisome for many.

Age differences

Most people that remain in a campground for more than 5 days are typically over 60. They are retirees and that’s why they can afford to do it. We haven’t met many stationary young people at campgrounds. Most come and go over the weekend. While I love learning from the wisdom of older gentlemen, I cannot start a conversation about the latest iPhone. Surprisingly I miss talking about that stuff (just a little bit… and luckily there’s Twitter to help out with that).

Networking is more difficult

A strong relationship develops with time. I regularly join meetups in every place I visit so that I can meet new people. But if I stay in a place only for one month at most, I don’t get to hang out with the same people more than 3-4 times. Clearly not enough time to develop a strong bond with a person. Keeping in touch with internet helps bridge the gap, but there’s no substitute for in-person interaction.

So what’s next?

We are currently staying in Myrtle Beach, South Carolina until the second week of November. We are thinking of heading toward Florida after that. The weather has been very kind and has provided us with a very new experience for both of us. Having lived in northern climates our whole lives, we’ve never been able to wear shorts at the end of October. Temperature is 73F. Weird, and lovely.