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My personal headcanon for Ash Ketchum has always been that regardless of if his dream ever came true he'd never truly stop traveling and learning. Because despite "becoming a pokemon master" being his goal if you actually sit down and watch like Any episode of Pokemon the thing that always holds true is his curiosity and desire to learn everything he possibly can related to pokemon. And he'll try anything to! He did contests and the battle frontier. He'd do those silly little shows with Serena if they'd let him.
So I like to imagine him continuing on in life as this nomad who people don't automatically recognize as anyone important ya know? Just this goofy guy going from place to place always lending a helping hand and hes got a cute lil pikachu on him. And hes often lost somewhere with a friend just exploring the woods to see if he'll find anything cool. Ya know, as hes always been, but older now. And its only once hes drifted once more do you maybe stumble into an article on the pokeweb about him and are like... that guy??