Being an individual verse wanting to fit in!

Question: Why do people say they're going to be an individual but then they try their best to fit in and become something totally opposite?
Answer: Have you ever seen High School Musical? You know that song called "Status Quo". Here's a few of the lyrics:

Zeke: You can bet There's nothin' but net When I am in a zone and on a roll But I've got a confession My own secret obsession And it's making me lose control
Jocks: Everybody gather 'round
Zeke(spoken): Well if Troy can tell his secret than I can tell mine...I bake
Jock(spoken): What?
Zeke(spoken): I love to bake! Strudels, scones, even apple pandowdy
Jocks: Not another sound Zeke(spoken): Someday I hope to make the perfect creme brulee Jocks: No, no, no, nooooooooooo No, no, no Stick to the stuff you know If you wanna be cool Follow one simple rule Don't mess with the flow, no no Stick to the status quo

"We forfeit three-forths of ourselves in order to be like other people."
Arthur Schopenhauer

Think about yourself. How do you react to wanting to be an individual versus wanting to be liked? I could go into a lot of communications theories with this that tells you exactly why we act the way we do. But here's the bottom line. We define our "self" internally and externally. Internally we define ourselves by who we want to be. Externally we define ourselves socially by who we interact with. So basically who you are is a combination of you and the people in your life that you surround yourself with. So this explains why its so important to us, as people to be accepted by the social groups that we are a part of. This is also why its important that we surround ourselves with the right kind of people that are going to help us create and good definition of ourselves. So knowing all of this consider that when you are a baby, you are defined mostly by your parents. But as you get older you begin to discover the rest of the world. That is the period that most of you are at. You are discovering what else and who else is out there. This can be really disconcerting at times, which results in uncertainty and insecurity. And since each person is trying to figure out who they are its really difficult to help other people to figure out who they are. How can I be defining someone else if I don't even know who I am? Therefore, this results in the need to be and individual but also the need to fit in, which sometimes looks like two things that are opposite of each other. How can you be both? But the truth is that you need both. The truth is that you are made up of both.

So in considering this, how can we affirm people in the individuality? How can we encourage who they are on the inside so that they feel more confident in social settings? How can we make people feel like they can be individual and still fit in?