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If you’ve ever wondered what it looks like to travel or relocate with a specific purpose in mind — whether chasing a sport, a skill, or a craft — or what life is really like in two of the Midwest’s most underrated cities, then take a listen as my guest Wade shares his experience training for pro wrestling and speaks about his home city of Chicago and his extended time in St. Louis.
Originally from Chicago, Wade is a filmmaker, documentary maker, and funeral industry professional who took up pro wrestling training as part of a passion project — spending two years immersed in a world that connected him with names like Carlito, Scotty 2 Hotty, Hornswoggle, and rising AEW talent. He also spent extended time in St. Louis with his wife, getting to know the city not as a tourist, but as someone living in it.
In this episode, Wade takes us through Chicago’s food scene, sports culture, neighborhoods, and hidden gems, before sharing his honest take on navigating the city’s reputation. He then shifts to St. Louis, covering local spots, community events, and what slow, intentional time in a new city can do for your perspective. His travel topic digs into what it really means to travel or relocate for training — the commitment it demands, the community it builds, and why staying focused on your purpose is everything when a new city is full of distractions.
After the interview, Triston shares thoughts on designing travel around a goal and what it means to pursue a craft with intention.
Main Points & Some General Points/Stories Discussed
Location: Chicago, Illinois & St. Louis, Missouri Travel
Topics: Traveling to Train for Sport & Committing to Your Craft
Main Points
- 00:00:00 – Cold Open
- 00:01:55 – Get To Know Wade “The Person”
- 00:11:35 – Insight on Chicago, Illinois
- 00:29:08 – Insight on St. Louis, Missouri
- 00:41:03 – Get To Know Wade “The Traveler”
- 01:02:56 – Travel Topic: Traveling to Train & Build Skills
- 01:24:30 – Rapid Fire Questions & 30 Seconds of Glory
- 01:28:44 – Post Interview: Triston on Designing Travel Around a Goal
General Points/Stories
- Wade shares how a documentary project led him to two years of pro wrestling training at CSW in Chicago
- Wade explains Chicago’s surprisingly deep pro wrestling scene and the major talent that passes through
- Wade discusses the wrestling hubs across the US — Florida, Iowa, Wisconsin, and Illinois — and what makes a region become a hub for a sport
- Wade reflects on how to stay focused on your training purpose when a new city has a lot to offer
- Wade speaks on the value of bringing trusted people into your pursuits and building community around your craft
- Wade shares what extended time in St. Louis taught him about slowing down, reflecting, and experiencing a city like a local
- Wade talks about Chicago’s safety reputation and offers a grounded, honest perspective on navigating any city well
- Wade explains how his definition of success has shifted across careers in funeral work, filmmaking, and wrestling
Things to See and Do
Chicago, Illinois
- Harold’s Chicken — beloved local fried chicken chain
- MacArthur’s Restaurant — family-owned soul food institution on the west side, frequented by major artists
- Al’s Beef — Italian beef sandwiches and Chicago-style hot dogs
- Aurelio’s Pizza — Wade’s personal favorite for deep dish
- Giordano’s — iconic deep dish pizza spot
- Museum of Science and Industry — one of Wade’s favorite Chicago attractions
- Shedd Aquarium & Field Museum — classic Chicago cultural stops
- Brookfield Zoo & Lincoln Park Zoo (Lincoln Park Zoo is free)
- Navy Pier — waterfront attraction in downtown Chicago
- Chicago Bulls games at the United Center — lively crowd and great atmosphere win or lose
- Wrigley Field area — iconic Cubs ballpark neighborhood worth exploring
- CTA Train System — blue, red, green, brown, purple, and yellow lines cover the whole city
St. Louis, Missouri
- Forest Park — large, scenic park ideal for walks and outdoor time in the heart of the city
- Soulard Market — lively farmer’s market running every Saturday
- German Cultural Society Center — community events bringing different cultures together
- Protagonist Café — intimate independent coffee shop with used books near the Soulard area
- Cassandra’s Kitchen — solid local food spot with a mix of cuisine styles
- Lake of the Ozarks — a short drive from St. Louis, ideal for scenic riverside getaways
- Ferguson — neighboring area worth exploring for a quieter, community feel
Resources Mentioned
- CSW (Chicago pro wrestling promotion and training facility where Wade trained)
Connect With Wade
Watch his films on Vimeo: vimeo.com/wadefilmmaker777
Connect With The Backpacker Society
🎒 Explore more travel conversations at backpackerssociety.com/
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