Have you ever wondered why pickleball can feel almost ridiculously addictive? Why you can play for two hours, be hungry, exhausted and fully intending to leave — and then somebody says, “One more game?” and somehow you’re back on the court?
Benjamin Grant may have the answer. Benjamin is a former professional player who still competes as a 5.5 player, while now coaching amateurs at New York's CityPickle and advising professional players on the PPA and APP Tours, bringing a philosophical, strategic, and high-energy approach to helping with movement, shot selection, and mechanics needed to play smart and creative pickleball.
Tracie found Benjamin through a brilliant article he wrote for The Dink about flow, the psychological state where the challenge in front of you perfectly matches your skill level and you become completely absorbed in what you’re doing.
Everything else disappears.
Your phone. Your inbox. What you’re having for dinner. Whatever ridiculous thing you were worrying about five minutes earlier.
Contest ends 9/30/26
Because in pickleball, if your attention wanders too far, there’s a decent chance the ball will remind you to come back.
Benjamin explains why pickleball is particularly good at creating flow: the small court, fast exchanges, constant involvement and possibility of finding competitive games at almost any level. You don’t necessarily need four equally skilled players, either. Sometimes the right combination of ages, abilities and strategies creates exactly the challenge everyone needs.
And maybe that explains why we’re always looking for a slightly better game, a tougher opponent or a longer rally. We’re chasing that wonderful feeling when everything clicks and we are completely, blissfully there.
In this episode, you’ll hear:
What “flow” actually is — and why pickleball creates it so easily
Why balanced games matter more than perfectly matched players
How playing better opponents can help you find your next level
Why pickleball forces us to be wonderfully present
The community and connection that continue even between games
Benjamin’s 20-60-20 rule for choosing who you play with
Why “one more game” may be less about obsession than chasing one more perfect flow state
The big takeaway:
What keeps us coming back to pickleball may not be the competition at all — it’s the rare feeling of being completely absorbed in the moment.
Share this with a pickleball player who has absolutely, positively played their last game… until someone asks for one more and tell them to SUBSCRIBE.
Short, practical insights for recreational players who want answers.
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