Being weird and pursuing peers

Some people travel a long way to find signs of intelligent life. I just went online. (SDASM Archives)

In 2008, I felt like a weirdo.

I was running a business and didn’t know what I was doing, even though I had read every book I could find to help me. That’s not because I was failing; rather, I was starting to progress past the point where general advice could apply.

Plus, I had read Tim Ferriss’ The Four Hour Work Week, which got me fantasizing about a life in which I could travel around the world, working from anywhere. But that felt like something I should keep to myself. Sharing my ambitions felt like a swift way to destroy my career as a neighborhood music teacher.

In an effort to expand my business beyond getting paid for my own time, I had hired additional music teachers and opened a physical location. However, for all my hard work, I felt like I was moving backward.

There was a very short list of people I could talk to about my dreams and challenges, and an even shorter list of people who had been in my situation or knew how to help. Therefore, when I found The Tropical MBA podcast in 2014, I was delighted. Hosts Dan and Ian had not only built a business designing, manufacturing, and selling cat furniture and valet podiums, they were running it from Bali and elsewhere. They were living the dream. Best of all, they had built a community of similarly-minded entrepreneurs around them, hundreds of fascinating people who were happy to exchange ideas with someone like me.

This was the end of my loneliness as an entrepreneur. I started implementing what I was learning from the podcast and its audience, which made my business and life better. Even more importantly, I began to see that what I wanted wasn’t even that weird. In fact, it was achievable. I now had a map and a clear destination.

By 2017, I started attending in-person conferences sponsored by the TMBA’s private community, the Dynamite Circle. I hired a coach that I met in that community. Soon, I joined Akimbo workshops and began meeting entrepreneurs there. In all of these spaces, I realized that I could help others in the same way that my friends and colleagues were helping me. This brought me a huge amount of joy and satisfaction even as it strengthened my own learning.

True peers have not always been easy to come by. I grew up in a small town and went to a small school, where I was lucky to have a handful of close friends. In college, I struggled to fit in—what I wanted didn’t seem to match what we were all headed toward. As a young adult, I worked mostly at jobs where I was surrounded by children, as opposed to fellow adults. To have a rich community of peers is a privilege I am grateful for. I know what it’s like to be without it, wondering whether you’re on the wrong track and everything you want is unrealistic.

When I finally had the resourcefulness, courage, and humility to surround myself with other entrepreneurs, I learned that I’m not the only weirdo. I saw that there were others who were going after similar goals, and I could follow their example. In fact, finally achieved my dream of location independence, in February 2020—just in time for the rest of the world to shut down and start working remotely, too. Oh well. However, now at least I know it’s possible. Time to start moving toward the next dream. With the help and support of peers and mentors, I know I can make it happen.

If you’re feeling stuck and lonely and isolated, know that there are others out there who feel the same way. It can be difficult to break out of a long history of feeling like no one understands, but the world is a big place and there’s room for every kind of dream, no matter how weird. Chances are, there are others out there who get it. If you are willing to put yourself out there, you will find them. And if they haven’t gathered, maybe you can lead them.