Hmm ... my parents were proud of me when I was in high school, working, on the swim team, and maintaining well above honor roll GPA, as well as helping with my bro and sis.
In college, that kinda went away as I switched to working and drinking, and maintaining a D average.
When I dropped out my mom was not very proud of me, nor was my father.
Afterwords, I've climbed the corporate ladder a bit and have a pretty sweet gig as a lead analyst. I have a house and make a decent living. I'm in a healthy relationship and it's been smooth sailing for the last year with her ... so I think my folks are happy.