ELAINE: Follow your dream. You'll still be the youngest lawyer in the country.
This seems more like Elaine's dream for William than William's own dream for himself. Elaine wants her children to maximize their potential, but she's hesitant to acknowledge their actual dreams and passions. For William, this passion turns out not to be law but rock writing.
ANITA: This song explains why I'm leaving home to become a stewardess.
For Anita, and later for William, your identity and the music you listen to are permanently intertwined. Rock music speaks to Anita so deeply that she actually uses "America" by Simon and Garfunkel to explain her decision to leave home.
ANITA: One day you'll be cool.
Anita leaves William with two things when she departs: her record collection and this prophecy. Those albums would soon solidify William's identity as a lover of rock and roll and spark a lifelong exploration of what it truly means to be cool—or uncool.
PENNY LANE: We are not groupies. Groupies sleep with rock stars because they want to be near someone famous. We are here because of the music, we inspire the music. We are Band Aids.
The first thing we learn about Penny Lane is that she is no groupie—she is a Band Aid. She is firm in this conviction and confident in her identity—which, like William's, is firmly grounded in her love of rock and roll.
LESTER: Don't let those swill merchants rewrite you.
Lester, as resident life coach and rock guru, warns William not to lose his identity. The big rock stars and the big rock magazines will try to influence William, he says. But it is William's obligation—to the music and to himself—to stay strong.
PENNY: I always tell the girls, never take it seriously. If you never take it seriously, you never get hurt; if you never get hurt, you always have fun; and if you ever get lonely, just go to the record store and visit your friends.
Life lessons from Penny Lane?
If only she could follow her own advice. She does end up taking things seriously, and she does end up getting hurt. William and Russell make the same mistake. But, of course, it's not really a mistake—if you never take things seriously, you've got nothing to lose… but you've got nothing to gain, either. Sometimes life hurts, and if you never get hurt, you're probably not really living.
RUSSELL: See, I grew up with these guys, but I can't play all that I can play. I'm past them as musicians. But the more popular we get, the bigger their houses get, the more responsibilities, the pressure, you know—the harder it gets for me to walk out on them.
Russell knows that in some ways, Stillwater limits his potential. He is conflicted, because as a musician, he has certain aspirations. But he also has this responsibility he feels toward his band-mates. His preoccupation with this conflict, however, prevents him from fully fulfilling either responsibility.
RUSSELL: From here on out, I am only interested in what is real. Real people, real feelings, that's it, that's all I'm interested in.
For a night, Russell becomes obsessed with everything that is "real." There's an integrity or purity that he thinks is disappearing from his life and from the world of rock and roll. Of course, in Russell's pursuit of what is real, he winds up shirking his responsibilities to the band and tripping on acid on a rooftop, yelling stuff like "I am a golden god." In other words, he gets more out of touch with reality than ever.
LESTER: The only true currency in this bankrupt world is what you share with someone else when you're uncool.
Lester's line to William in his greatest moment of self-doubt is a profound commentary on human connection. Lester knows what it feels like to be down and out, and he's there for William when no one else is.
RUSSELL: Maybe we don't see ourselves the way we really are.
Russell finally shows some self-awareness when he learns what William wrote about the band. It's one thing to be sure of yourself and your identity, but it's a whole other thing to delude yourself about the truth. William's piece is an eye-opening moment for the band: they have the power to change for the better.
They just have to accept that there's a problem first.