How far would you go to share your love of pickleball, meet people across America, and prove that joy, community, and adventure can all fit into one unforgettable journey?
In this episode, Dean Matt Dean shares the remarkable story behind his 48-48-48 Challenge, an ambitious pickleball adventure that took him by plane to 48 states in less than a month to play pickleball with people from every walk of life. A longtime CFO, pilot, filmmaker, author, and proud owner of his own aircraft, Dean talks about how he first discovered pickleball after moving from the Chicago area to Florida, and how the game quickly became more than just a hobby. What started as curiosity soon turned into a big dream inspired by endurance athletes and his own desire to combine flying, travel, and pickleball into something totally unique.
Dean explains how he planned the route, coordinated courts, transportation, housing, and local players in nearly every stop, and ultimately traveled more than 9,000 miles while playing pickleball with senior pros, local club players, public officials, Special Olympics athletes, and even a 97-year-old woman who became one of the most memorable people on the trip. Along the way, he shares stories from places like West Virginia, New Mexico, California, Wisconsin, Idaho, and beyond, revealing how each stop offered its own version of hospitality, joy, and human connection.
This is a fun, uplifting, and inspiring conversation about pickleball, aviation, the 48-48-48 Challenge, Florida pickleball, senior pickleball, community, travel, friendship, resilience, adventure, and the life lessons that remind us there is nothing quite like pickleball for bringing people together, softening our edges, and showing us the best of what people can be.
📘 Our book Life Lessons from Pickleball™ is now available on Amazon
Order the book here: https://a.co/d/0bHPFYve
A collection of short, true stories from players around the world about community, resilience, and joy through the game of pickleball.
A portion of proceeds supports Operation PaddleLift, through the Global Pickleball Federation, distributing paddles, balls and nets to underserved communities around the world.
Contact us: www.lifelessonsfrompickleball@gmail.com
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Music gifted to us by Ian Pedersen: @ianpedersen
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