Five Things I Do to Keep My Digital Nomad Journey Alive
Updated: Jan 4, 2022
Over the past two years of being self-employed, I’ve been experimenting with designing my work around my life. This intention led me to Asia to experiment with living as a digital nomad and then to Taiwan, where an amazing relationship has given me a deeper reason to keep this journey alive.
While Taiwan has been a home base, I’ve also lived and worked in Bali and Chiang Mai. Bali and Chiang Mai are vibrant digital nomad communities, but that also means it’s easy to settle into familiar comforts. In Taiwan, I’ve appreciated the often uncertain and uncomfortable states that come with learning a new language and adapting to new cultural and social norms. I’ve had to develop what the poet John Keats called “negative capability.” He defined this as “the ability to contemplate the world without the desire to try and reconcile contradictory aspects or fit it into closed and rational systems.” While being in a place like Bali may make it easier to land a new project, being in a world new to me is more valuable in terms of developing a deeper capacity for learning how to live.
Anyone on a self-employed path faces the inherent uncertainty of the modern “how do I make a living” question. Over the past two years I’ve experimented (with some success) with making money through online courses, writing, consulting, coaching and a podcast. In the process, I’ve noticed that I often take a different approach than many other freelancers and digital nomads. Instead of focusing solely on the outcomes (read: money), I embrace a set of principles which are not “hacks” to get rich quick, but are instead my way of staying true to the person I want to be throughout the journey. Here’s how I would define these principles for myself.
#1 – Follow My Curiosity
I’ve been writing about the gig economy and the future of work for several years. I’ve found that much of the public conversation around these topics is driven by a media narrative that tends towards outrage and panic. Instead of just reacting to this conversation, I’ve decided to engage with my own thoughts, often spending hours writing essays on related topics. This past year, I spent 25+ hours writing and researching the talent platform economy and published an article on it. I had no goals with this other than to add a deeper perspective to the conversation, but the article was shared widely within the industry and several founders of companies ended up reaching out to me. Putting this out into the world has enabled people that are thinking about the same questions to reach out to me and has also given me the positive feedback signal that says “perhaps there is something further here, go deeper!”
#2 – Default to Generosity
One of the biggest traps of freelancing and self-employment is the scarcity mindset. When I am in this mindset my brain is screaming that I need money or that I must find a paying gig. While this may make sense in the short-term, it blinds me from a key aspect of what helped me become self-employed in the first place: building long-term relationships with people or companies that inspire me. Whenever I hear someone struggling with something I can help with, I try to be as helpful as possible.
In Taipei, I’ve volunteered to help people with English and also helped a local company update its website. I do this because I love helping others, not with the expectation of anything in return. It’s also a way for me to show that I care and want to build meaningful relationships in this country. Will these people help me land paying gigs down the road? Perhaps, but that’s not the point. The point is for me to keep learning and to keep engaging with people I actually want to work with.
#3 – Share My Story
Sharing your story in public can be terrifying. What will people think? This can seem like a scary thing, but my experience has been almost 100% positive. Through sharing my story, I’ve connected with people dealing with similar challenges, found others sharing similar curiosities, and received direct requests for business opportunities. While everyone cringes a little when they see shameless self-promotion, people will always be attracted to a good story. I’ve tried to chronicle my own adventures of self-employment in an honest way, including the messiness and the uncertainty of it all. This enables people to connect with Paul the human who has problems and challenges just like me instead of just Paul, the freelance consultant.
#4 – Share Others’ Stories
A few years ago, I found myself constantly meeting people who had amazing stories. I wished more people could hear these stories. So I turned my wish into an action and launched a no-frills podcast. My goals were to learn from the experiment and figure out if it was something I wanted to keep doing. After several episodes, I realized it was in fact a long-term thing and over time it has evolved from a fun, creative project to a more serious endeavor focusing on how we can reimagine work. It’s also a great excuse for me to connect with people I’m fascinated by as I travel. From interviewing Christine Bader about living with her family in Bali to YuTing Chiu making her own instruments in Taiwan, sharing other people’s stories has been a great way to build genuine connections with those that inspire me, reach people that are interested in my work, and continually learn about fascinating topics.
#5 – Curiosity Conversations
Ever since reading Bryan Grazer’s book, A Curious Mind, I have been inspired by how he attributed much of his success to “curiosity conversations” he had with people in the movie industry. He reached out to otherwise famous people and asked them to talk about about their careers. He asked them about themselves in a genuine and curious way. I’ve embraced this in my own self-employment journey, reaching out to people that I am inspired by.