I think that's exactly what he grappled with. He was drawn to Luke and Leia and felt some loyalty to them, but they came with this rebellion thing that he didn't want to get involved in.

In some ways, the movie Solo really showed how he always had these heart-of-gold tendencies, despite trying to be an outlaw. Then by the time Luke and Leia show up, the outlaw part is catching up with him just when he's found people who can convince him to care about the bigger picture.

Also, in Solo he tried to appear more jaded than he was (? perhaps?). I always imagined him with a soft center, even in TFA it came across to me. Like he was mildly cynical, but the whole "too cool for school" was just an act.