We've already seen Gary go from a Pokémon trainer to a Pokémon researcher and the rest of the cast won't be travelling around forever either. We may never see what happens later, (unless we get an epilogue or series set a few decades later,) but it is interesting to speculate. Let's try to avoid shipping debates here, though.
Ash will probably manage to win a tournament eventually and once he is established as a powerful trainer, his career will probably reflect that. I see him being hired by the Pokémon League for duties 'on the field'. One role will be bodyguard for the tournament torches since he seems to already do that anyway.
Brock could make lots of money selling his Pokémon food.
Misty will probably remain as Gym Leader, (even if she takes a break to travel with Ash later in the series.) Max also looks set to take over the Petalburg Gym when Norman retires, possibly implementing a scheme similar to the game version of the gym.
Jessie, James and Meowth... will probably continue their attempts to capture Pikachu. Or maybe they will see sense and retire into a legitimate lifestyle. (They already nearly did in Vanity Affair.)
Ash will probably manage to win a tournament eventually and once he is established as a powerful trainer, his career will probably reflect that. I see him being hired by the Pokémon League for duties 'on the field'. One role will be bodyguard for the tournament torches since he seems to already do that anyway.
Brock could make lots of money selling his Pokémon food.
Misty will probably remain as Gym Leader, (even if she takes a break to travel with Ash later in the series.) Max also looks set to take over the Petalburg Gym when Norman retires, possibly implementing a scheme similar to the game version of the gym.
Jessie, James and Meowth... will probably continue their attempts to capture Pikachu. Or maybe they will see sense and retire into a legitimate lifestyle. (They already nearly did in Vanity Affair.)
