Take, for example, friends. I don't have many friends. But because I've lived so long without friends, I really appreciate the one or two (good) pals I have now. Someone who has been popular their whole life has nothing to contrast it to. They can't see if their life is getting better, in that aspect. But I know what it's like to be lonely, so I know my life is slowly getting better. (Even if they are only in-school friends. In a way, I like it like that. Weekends are a time for me to be alone. I'm surrounded by people five days a week! Not to sound like a misanthrope, or anything...*eyes wander*)
It's kind of like the people who rose from poverty to achieve wealth, as opposed to people who were born into riches. Who do you think feels more successful?