1. tennis- just love playing the sport, couldn't imagine a better way to make a living
2. 1st Line C for the leafs- just a dream position. I don't even care if the team sucks like it does now, I would be incredibly happy with the leafs either way. Hard to not have this as my #1 job, but tennis with all the nice vacation spots you would play at has to be top.
3. 2b for the yankees. i hate the team so god damn much as a jays fan, but I can't imagine a better organization to play for. Not a bad spot to be playing alongside Jeter and A-Rod in the infield.
4. WR for the colts- maybe the best QB of all time throwing you the football, making you look like a star? Hard to pass that up. Manning could make almost anyone look great. That would just be a very fun offense to be apart of. Playing WR opposite Fitz would also be great though just because of the player he is as well as the person he is. Harrison would be great mentor though.
5. PG for the Raptors. Not a great organization at all, but have to play with the hometown team. Hard to imagine a better feeling than taking your hometown team from mediocrity to the top.
I'd much rather be a top tier player loving the game and improving to be the best rather than some no name that doesn't have to do much. No way to want to live a life imo.