opening a bar (as shown to be a fantasy of his)

opening a gay bar (my preferred ending)

working with kids, potentially at a home like sonny's

working as a mechanic, eventually specializing in vintage cars

becoming the new bobby, helping the next generation of hunters

being a stay-at-home dad with his husband castiel as the breadwinner (cas doesn't work either he just steals money from rich assholes using his powers and calls it being a breadwinner)

(he's with cas for all of these btw in case that wasn't obvious)

spending like a good decade traveling the world via angel express and enjoying his retirement from hunting

becoming a rock star with a cult following, a significant portion of which love sharing around conspiracy theories that he's actually a serial killer who faked his own death and started fresh with a new identity (no one seriously believes this)

becoming a sheep herder (it's the closest thing to a modern-day cowboy he can get. he gets to wear the hat and everything)

moving to hollywood and becoming an actor under the pseudonym jensen ackles

becoming a successful writer purely to spite chuck, outselling the supernatural series easily and receiving rave reviews for his refreshing style and devastating depictions of childhood trauma and breaking the cycle of abuse

building a space ship and searching the galaxy for intelligent life