Decisions and Regrets

I do not regret the decision I made to retire my law practice, sell my house, and go off on my epic road trip. I regret pretty much every decision I’ve made since I returned to Green Bay. Remaining in Green Bay For two years straight, I contemplated leaving Wisconsin once and for all, and for two years straight, I Read More …

The Myth of the Swindling, Freeloading Poor

In a Facebook thread discussing charity and giving to the homeless, someone challenged me to explain how I can know that a panhandler isn’t pulling a scam by pretending to be poor or homeless in order to get easy money. Cogito, Ergo Sum If we get obnoxiously philosophical about it, who can truly know anything? There is no way for Read More …

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 …

Dreaming of Paradise

I had the most amazing dream last night. Remy and I were living in a cave in the desert. It was dark and kept us cool during the day, and a fire would keep us warm at night. There was a long and winding path from the cave entrance to our den, so wind wasn’t really an issue. Deeper into 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 …

Job Satisfaction & Generation Lifestyles

Last night, I was reading a post from one of my hitchhiker friends on my Facebook feed. In that post, he explained that he had traveled 200 miles that day and was flat broke. He used a gift card to buy dinner and coffee, and then cashed out the rest for beer money. When I see posts from him that Read More …

Welcome to the Freak Show

During my trip, I felt undeserving of the title “crust punk” or “gutter punk” because I had a cushy truck with air conditioning. I was living a more comfortable life than the other punks I had met. But now that the trip is over and I’ve settled into my new temporary living conditions, I think I have earned the title. Read More …

Summaries of Days 34 & 35, and Beyond – Epilogue & Analysis

Note: Sorry this one got posted so late. I think it took five days for me to get around to this one. The trip is now officially over. I returned to Green Bay yesterday (Monday, August 8 – it might be a few days before I have enough data signal to get this uploaded). I am now in Nicolet National Read More …