I agree with Awakening: the People-Pleaser route is very overrated, because anyone who works too hard at pleasing other people will probably also have an inner taskmaster who's never satisfied. I don't think my parents pushed me much to achieve. They didn't have to. I saw people around me who did better, and I became frustrated by my own lack of achievement.
Eventually, I finished college and have taken jobs that don't challenge me much since that time. But that doesn't stop me from hearing the voices from friends and family saying I should do better, have a better job, make more money, get married, whatever....
I may not have a lot of answers but I know I can't put time frames on anything I do any more. I may not do much right, but I will always do something right, enough to never give up.