This is me in January of 2019, in Jackson Hole, Wyoming. That winter, a couple friends and I took a week-long trip to Jackson, WY. We spent 3 days skiing (or snowboarding) and 3 days on snowmobiles, and believe it or not, it was technically a work trip.
Let me back up a little bit to 2014, the year I read Tim Ferriss’ iconic book, The Four Hour Workweek, for the first time. This book opened up my world and introduced me to the concept of lifestyle design. Tim would explain it better than I, but to me it meant intentionally setting up my life in a way that works for me. The philosophy bloomed from the seed of a belief I already held – that the traditional way of doing things didn’t work for me. I didn’t want to find a job, work for 30 years, save my money, and eventually be free to live my life how I want, only after I retire. I knew there was a way to design my life in freedom now, and to live a life built for me regardless of existing standards or norms.
This philosophy shaped and continues to shape my entire life and career, as I continuously optimize for lifestyle, growth, and experiences over money or status. It’s an ongoing and arduous process, but a worthwhile one.
In 2018 while I was living in Charleston, SC working as a budding videographer, some friends and colleagues planned this trip to Jackson Hole with me. I wondered if we could turn this into a work trip and get paid for it. I mean, we were going to be getting epic footage on the trip either way, so why not pitch some companies and see if we can create some value for them while we’re doing our thing?
So that’s exactly what we did. I spent a few weeks cold-calling outdoor gear companies, telling them we were going to Wyoming and we wanted to feature their gear to make some marketing content for them. Eventually I got on the phone with Big Bill, and after finding the link between their needs and our plans, they were on board. They loved the idea. They paid us decent money, gave us free gear, and we had a blast creating awesome content for them which they still use today.
To me, this photo represents freedom. To quote the 12-year-old ski phenom, Kai Jones, “I just wanna fly like a bird.” This photo isn’t just about the freedom to fly like a bird on a snowboard, but to do so every day, no matter where you are in life or how old you are. I decided a long time ago I wouldn’t wait for retirement to set myself free.
Want more stories like this? Sign up below and I’ll send you a fresh one every Friday.