Five-Minute Friday | Digital Nomad Progression

This is a quick run-through of my journey to become a digital nomad - that is, a rundown of all the businesses I have had that have let me travel the world and create freedom in my lifestyle.
I often talk about being a digital nomad when asked to speak publicly or when presenting workshops or keynote speeches. Afterwards, people often come up to ask how I did it - how I became a digital nomad. But really, until you do it, you can't know what it is going to be like.
It's different for me than for anyone else.
When I talk about being a digital nomad, you don't hear about the boring things that go on behind the scenes; the endless following-up with prospective clients, business partners, and sponsors, the ceaseless efforts to try to make something happen, the thousands of hours of work that go on at home - unobserved, the head-banging frustration to figure things out, obsessing over whether something should be done this way or that, and the painstakingly small, repetitive actions that must be performed to insure success. These behind the scenes hours don't make for compelling stories, but know that every entrepreneur has to put in this time.
My journey to become a digital nomad started with the desire to be an entrepreneur. Although I was interested in full-time travelling eventually, I didn't let the daunting nature of this goal stand in my way. I just started with a coaching business. As a professional cyclist, I taught younger cyclists how to go pro. I trained them to become better athletes and to be better racers. I had clients and I was charging about $250 a month. When I decided to leave grad school and go abroad, I looked towards Asia and South America, places where you can live for about a thousand dollars a month. So, I needed four clients to equal my cost of living. When I had that, I basically knew that I could travel indefinitely.
That gave me the confidence to go to Vietnam, my first country. There was a time when these coaching clients graduated and moved on. I didn't have clients or income for some time and that was when I started the Art of Adventure podcast. Just like anything where you expect to get rich quick, podcasting was not the scheme I expected it to be. Art of Adventure is largely a free show but lots of people kept asking me how to start a podcast. They asked for help, walk-throughs, and advice. So, I started hosting podcast launch groups where people would come over to my house to practice interviewing and to learn how to set up a podcast. I helped a lot of people by podcast coaching and would make about $2000 per month.
At the same time, I was giving a lot of talks. I was speaking for free because I knew that I wanted to be on stage. Eventually I realized that, with everything I had learned from podcasting and all the books I had been reading, I could teach this stuff and get paid to speak. Then on Episodes 48 and 49 of the Art of Adventure podcast, I had David Wood as a guest and he talked about how easy it is to start a coaching practice. I ended up hiring him to teach me how to become a coach and how to coach more broadly about business and life. And so, that's how the coaching branch of my business was born - an idea from a guest on the podcast!
With that said, I've taken so many ideas from guests on the podcast.
A later guest suggested that I should write a book. Eventually I would turn content from the interviews I had done for the podcast into my book, Superconductors. I launched it as a crowdfunding campaign on Publishizer, who is now a sponsor of the Art of Adventure podcast.