How I Stumbled into Digital Nomadism and Backpacked Around the World

Matthew Boutte
The Startup
Published in
5 min readJan 10, 2020

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In the past two and a half years I’ve backpacked through North and South America, Europe, Africa, and Asia, visited 25+ countries (I have a pending Global Entry application and I’m really hoping that I remembered to list all of them), sailed between two continents, lost (and regained) the ability to walk in Colombia, lost (and regained) the sight in my left eye in Paris, and gotten a rental car stuck (and unstuck) in the sands of the Sahara. Next up is a one way ticket to Norway with a Scandinavian rail pass and a quest to see the northern lights (I got skunked when I tried last year in Iceland). All while being self employed online and earning six figures. My parents still can’t wrap their heads around it and always ask me how I afford to do it. I think they think I work for the CIA.

If you had asked me three years ago about any of that, I would have stared back at you blankly. None of it was even a blip on my radar. I didn’t know what digital nomadism was and had never met a backpacker. But that all changed pretty quickly when I got fed up practicing law and a friend called me out of the blue and asked me if I wanted to go to Japan.

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