Fortune Favors the Bold

The Two Bartlets Many people lead lives of contradiction, toeing a delicate line between what they want and what they are comfortable with. One of my favorite cultural examples of this comes from The West Wing. The stories of President Bartlet (and his administration) oscillate between doing the right thing (at high cost or risk) and going the politically-safe route. Read More …

An Open Letter to “Normies”

In my effort to teach my old self some new tricks, I was poking around on Google the other day and typed “how to survive as a drifter” into the search bar. These following three results caught my eye and are the purpose of this post. What It’s Like Living as a Crust Punk Reddit: I want to become a Read More …

Teaching an Old Dog New Tricks

Sitting here today, I would describe myself as a man who has tasted true freedom and desperately wants to return to life on the road. Or – at least – to have the freedom once again to travel on a whim. It is possible. I know several people who have made it work. Some of them run location-independent businesses and Read More …

Reflections of a Rubber Tramp, One Month Into a New Job (and One Week Into a New Home)

Yesterday, I drove to work along my new route from my new home, and I passed by a Motel 6. I suddenly became nostalgic for the days when a stay at a Motel 6 was a luxury. What, with their flat beds, hot water, and ice machines – they were an oasis during my rubber tramping days. Honestly, it doesn’t Read More …

My New Tramp Name

Something pretty special happened to me this past weekend, and it was so special, that I almost didn’t notice it happened. I finally received a bona-fide tramp name. Bones christened me “Captain”. When he first started calling me “Captain”, I must have dismissed it in my mind because – over the years – many friends have given me many one-off Read More …