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Reader question: What does this sentence – As a teenager, he always felt like he was on the outside looking in – mean? My comments: It means that as a teenager, he felt kind of like a don’t belong. In other words, he was not one of the boys. That is to say, he did not fit in. He was not popular, and he felt lonely. And that feeling is one of failure – to be left out of what is called the inner circle. The idiom “on the outside looking in” is the thing to learn here, and people who are “on the outside looking in” are generally people who are close to a group but are not exactly part of that group, at least not part of the core group. Recall your own teenage years. Did you ever have your teacher tell you to stand outside the door as punishment for violating some school discipline? You keep speaking for instance with the student at the next table after the teacher have called the class to be quiet a few times. Anyways, the teacher grows impatient with you and thus orders you to stand outside the door while class resumes. Have you ever had that type of experience? Well, first of all, I’m sorry for evoking an unpleasant memory from school. In a perfect world, teachers should never do a thing like that to a student. Ideally, schools should not have any disciplines to enforce at all but the real world is not perfect. Reality is not wishful thinking, i.e. it’s not something to wish for. It is what it is. And the reality remains that schools always have disciplines and schoolchildren do violate them. | 
