Pretend that, for whatever reason, some people are making a movie of your life. And the people in charge of the soundtrack are amazing and can bypass any rules about licensing, yadda yadda, so any music ever written is up for grabs.
What songs would be in a movie about your life?
Not like, what song would be cool to have while you drive a car fast down an empty road, but what songs do you feel were very defining about you at a certain point in time? Or fit nicely with an important event? Or just generally seem to apply to you from an outsider's perspective? Go crazy with this. You can have a three CD movie soundtrack or maybe just a vinyl record with an A and B side.