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If I lived in the Pokemon world, I'd definitely be a teacher. Probably live in Violet City and work at the Pokemon School, but I'd travel to different towns and regions often to offer kids starter pokemon and just experience the world.
In my down time I'd try the Pokemon League challenge but it wouldn't be a priority. One day I'd like to be a gym leader in my own city where I can start a higher level Pokemon school. A place where I can teach people about the more subtle details of training and the world of pokemon - IVs, EVs, catch rates, the regions of the world, etc.
Duskull would've been my starter hopefully, and I'd specialize on ghost types, so I'd probably be replacing Morty in Ecruteak, and starting my school there. Top team would be my personal team and the one I'd use to challenge the league, bottom team would be my gym leader team that I'd select from depending on how strong the opponent is, like how they showed in Origins.
When I meet kids who are ready for pokemon on my travels, I'd like to give them less common pokemon as starters, stuff like Phantump, Spheal, or Baltoy. Just interesting Pokemon that they might not have otherwise wanted. The point is to see if they'd give up on their ambitions after getting a non-typical starter, or if they'd learn to love their Pokemon no matter what.
When I get old, I'd like to retire in Agate Village in Orre, hopefully with a wife. I'd still probably visit Ecruteak regularly to see how the school is holding up, and I'd still take joy in starting people off on their journeys.
I'd like to live my life with the philosophy of shaking off the stereotype that ghost trainers are all sad, lonely, scary old people - I want to be full of life and constantly pushing for people to be their best. Ghost type pokemon are the most full of life pokemon of any, after all - they could've moved on to the afterlife, but decided to hang onto life as a Pokemon and explore the world that way. That's where my inspiration comes from.
