xavier might work! had this guy working in an org connecting the homeless community with arts programs. was hoping he had his start in actually making art, but after a family crisis forces him to be more pragmatic about his life choices, he settles for a gratifying, if boring, operational role. the assistant (or really just a young coworker if anything) would preferably be a former charge (cal here works primarily with homeless youth) who eventually coasted their way into an instructor role because of their innate talent in (name your medium here). cal's more straight-laced than most and cut his freewheeling art school days early, so i could see him living vicariously through this young assistant, or perhaps inadvertently getting persuaded to join the debauchery against his better judgment.