Interview with Digital Nomad Aaron Freed

Aaron Freed

In this interview with Aaron, we will learn about his unique way of living the nomadic life which includes weekly location changes, boat hitchhiking and much more.

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Aaron Freed is a true nomad. He avoids traveling with airplanes (kind of ironic since he spent 12 years as a pilot in the US Air Force) and prefers motorcycling and hitchhiking sail boats (15 sail boats under his belt far).

Here are some insights Aaron shared with us:

Aaron is unique in his frequency of changing locations. Usually, digital nomads stay a few months before moving on to the next destination. When he isn’t sailing, Aaron prefers to spend only one week in a place before moving on to the next one. After separating from the Air Force, Aaron turned to entrepreneurship and real estate investing, until the crash of 2008. He then spent three years wrestling with next steps, wondering if should pursue a new career at the age of 40, or go for a completely different lifestyle. He chose the latter and started his nomadic journey.

Aaron believes that once you make a decision to become a nomad, putting a start date on your calendar will greatly increase your chances of actually making it happen. Aaron chose the nomadic lifestyle as a way to run away from his previous life that was not working well personally, professionally, and financially. He originally intended to go only as far as Beirut, where he would start anew. However somewhere in the middle of the Atlantic Ocean, he decided that nomadic life suited him and sought ways to sustain it.

Aaron finds boats by using a variety of boat hitching websites as well as dock walking (thus the title – “Boat hitchhiking and nomadic life”). He says that one doesn’t necessarily need sailing experience (although it certainly helps), and it’s only a matter of weeks if not days before a newbie can become a competent crew member. For those interested in boat hitching, he recommends that you start by reading about it on hitchwiki and joining one of the boat hitching groups.

When you’re ready to make the plunge, he recommends putting together a sailing resume and posting your profile on as many sites as possible (such as cruisersforum). When dockwalking, he doesn’t leave any stone unturned and has found boat maintainers to be one of the most effective ways of finding rides.

Aaron is a little jealous of non-digital nomads (nomads who don’t use the internet to get money) He feels that they get to experience greater connection with local communities that the networked nomad who spends his time looking at a computer screen. The lives of non-digital nomads have an ingredient of uncertainty and dependency which makes their journey more interesting, or at least different in an enviable way. Aaron is actually experiencing this dependency every time he boat hitches. Asking for help or a favor from someone creates connection.

Aaron says “Moving” is a great proxy for “Doing”, until you figure it out. With time, he’s learned to accomplish both simultaneously. When he felt stuck in his life, he was searching for a lifestyle that will create stories, and push to doing more. Interestingly, he is most happy when he gets to a place and feels at home, so the constant change is actually out of his comfort zone. However, he still manages to keep it up due to the benefits those moves bring.

Aaron says that avoiding situations in which you have to be in a certain place at a certain time will improve your quality of life as a nomad. Every commitment you make reduces your flexibility to move faster, stay longer, and be free to explore spontaneous possibility. Impulsive one-way tickets (or one-way boat hitchhiking in Aaron’s case) are the way to go. The skill Aaron is still trying to improve as a nomad is carrying less stuff. The less he has, the happier he is (and the less he looks like a tourist).

While on land, Aaron establishes weekly routines that help him organize his life. For instance, he strives to travel and grocery shop each Sunday, work and exercise Monday through Friday, sightsee and do laundry on Saturdays, and so on.. He finds that little routines and disciplines bring stability that is much needed when one keeps changing locations.

Check out Aaron’s website at

One Response so far.

  1. Marilynn says:

    I have fun with, lead to I found exactly what I was having a look for.
    You’ve ended my four day long hunt! God Bless you man. Have a nice day.

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