A 15 year journey of failure that led me to becoming a remote worker

I’d planned on being an engineer. The stable hierarchy would have managers hand me projects with deadlines and I’d earn a salary fulfilling my duties. But before I could graduate I caught the travel bug. I ended up dropping out of one of the best engineering schools in America to move to Europe in pursuit of a budding rugby career.

Yes, it was a double shock to my family and high school guidance counselor who had all expected me to finish school and definitely weren’t expecting the allure of such an unpopular sport in America would to lead me astray. This was the worst case scenario for me in many people’s eyes. I was easily distracted by new challenges and projects. So maybe I’d never graduate. 

Maybe they had a point. I was too distracted to take my future seriously back then. But I learned that once you’ve left your prescribed path, you can never truly recover. You’ll never be the golden child that you could have been. You’ll always have that blemish. So I embraced it. I gave up scoring my life on how near or far I was from that path. I started to look at what value I could provide and I found that depended heavily on where I was. No one in the US wanted an average looking, native English speaking, young man to work on television. But I easily found work in China and was paid a higher salary there than with any job I’d had in the US. 

Over the last 15 years I’ve proven my doubters right. I’ve been easily distracted, moving from country to country trying to find my place amongst the chaos. No longer was the path in front of me clearly illuminated. I was learning to see in the dark and rely on other senses to move forward. I learned that I couldn’t rely on systems like I’d been raised to. I would learn to deal with people and figure out what people needed and how I could provide value to them.

Unplanned travels since 2006

My myriad of interests lured me down many unrelated paths. From financial analysis and education to transportation and consumer technology, I found myself at conferences in Europe or Asia surrounded by a sea of loyalists to an industry I’d just picked up. Starting from behind meant I had to catch up quickly. I learned to put in the long hours, the extra sessions. I worked six days a week, often living with other colleagues in company housing. Sure, it wasn’t a life of total freedom but I felt I was finding out what I was good at, what I didn’t like and what came naturally to me. Managing other people, building a 3-year strategy, working the night shift, or the early shift, being the mediator, cracking down on bad employee behavior, and learning when to pull the plug on a failing project were all things I’d never done before. I felt these lessons were risk free as I could just move on to the next station if things went south. Again, the worst case scenarios other people were worried about would usually turn into new unexpected opportunities that turned out to be a step up.

I learned to look for opportunities, actively. I assumed the regular channels wouldn’t be kind to someone like me. I hadn’t stayed in the same industry. I hadn’t deepened my knowledge of any specific niche. Instead I was the jack of all trades, finding common ground with everyone but instilling confidence in no one because of my peppered past. So the opportunities I managed to find were mere cracks of light coming from the wall I knew I’d put in my own way. I helped a stranger’s girlfriend gain entry to a nightclub in Shanghai. Her boyfriend bought me a drink to thank me and we ended up talking for much longer than a thank you drink demanded. After discussions on the economy, philosophy, 90’s rock music, and AI language software he remarked that it was too bad his chemical manufacturing company didn’t have a guy like me on the payroll. I put my drink down and looked him in the eye telling him they could have one by Monday. He hired me to help train his Chinese domestic salesmen to expand the business to South East Asia and the Middle East. Moments like this one at the nightclub led me to unanticipated promotions to positions I never even considered myself qualified for. Odd highlights have included being introduced as a Love Doctor on a daytime television program, giving TEDx speeches, teaching children’s kung fu classes, leading philosophy workshops, and advising American investors on emerging Asian companies. 

Speaking at Techsauce (Bangkok 2017)

Through all of this I would meet people working online (full time or part time). I started a few pet projects with some friends testing our newly developed skills. Later I would find myself in situations dealing with clients overseas, or colleagues in different time zones. I was one of those people who already had a zoom paid account well before COVID hit us in 2020. My various interests kept my fingers in many pies simultaneously. I failed and learned how to balance the demands of remote work with a stimulating lifestyle. I’ve seen first hand what mindsets, strategies, and work styles are suitable for the Asian, African, European and North American markets. I’ve seen great ideas die slow deaths but have also witnessed ignorant managers get extremely lucky. 

In 2018 and 2019 I worked with CEOs sharing my perspective from all I’d learned on my journey so far. Their genuine thanks made me realize we could all use a mentor, no matter how far we’ve come. I have only had a select few during my travels but I treasured them. I wish I’d sought out more. In 2020 I reached out to some of my trusted companions in the remote work field. We’d met at digital nomad conferences annually since 2016 and together we have put together Remote Work Mentors. I’ve faced uncertainty, taken responsibility, and challenged myself in businesses all around the world. The worst case scenario people warn you about could be that crack of light that illuminates the first step on your new path.

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