20He’d be happier if he wasn’t a hunter
Throughout 14 seasons of Supernatural, Sam has made it clear plenty of times that on some level he resents getting forced into the life of a hunter. Dean seems to love it, but Sam wishes he could get away and lead a normal life. This isn't exactly specific to Supernatural as pretty much every
superhero seems to feel similarly about their own lives, but it still makes us feel a little guilty watching him.
At this point it's well established that Sam would be happier if he never became a hunter. He would have gone to law school and lived a normal life-- something that's actually been shown in alternate realities. Sam wants to get off the endless rollercoaster that is Supernatural, and Dean still gets uncomfortable whenever he brings that up.