I have a cool idea, actually.
You know how random things happen in the game, such as you getting a son in your youth team?
Well how about this... Say that as a manager your user made a lot of money from wages, but then you retired and made a new manager. Well, if the old user manager you made had made enough cash from wages, you could randomly see him taking over a club somewhere (like if he didn't make so much he'd take over a conference club, and if he really made big cash then he'd take over ManU or something

)
Seriously, how does that sound? It can be fun and also provide more relevance to the wage feature.