Leporello, the day you discover self-esteem, is the day you will wince to recall all the times you have whined about unfairness and the futility of your existence.
Do not whine about people who are born into circumstances better than yours; you must realize the golden rule of money: no one can be smaller than their money. If a man is equal to his money (as a self-made man who earned it most obviously is), his money will serve him; if he is not equal to his money, it destroys him. Look at all those rich kids who had it so easy and so good-what happens to them when they grow up? Justice catches up with all of them. The content of their characters determines the verdict of justice and the conditions of their lives; how many of us have heard and seen that classic cliche of the rich kid, who you used to envy, that grows up to die of an overdose, or gets drunk and dies in a car accident, or who goes to prison, or who just settles down into a living-dead state of booze and cheap thrills to pretend he is alive? Or the mega lottery winner who is dead five years later? The rule is absolute and unyielding: no man can be smaller than his money.
Believe in yourself. Not as an act of irrational defiance against whatever secret feelings of inferiority you harbor, but know that you exist, that your mind is your tool of survival and the arbiter of your existence. You must believe in your worthiness of whatever you desire, and you must understand that only your virtues can achieve anything that is worth having. If I gave you all my money today, it would mean nothing to you, you would still feel frustrated and hopeless; but it means everything to me, because I know the excruciating discipline and inhuman effort and ruthless devotion I exacted from myself to achieve it. And it's not that I've arrived at the pinnacle yet, but I got myself off the ground (which is the brutally hardest part) and I'm making strides, and I'm not looking back. It's wonderful. FYI, my greatest goal is to be a self-made millionaire.
Know that there is a hero inside you, but you can only realize him by your own free will. Recognize that you possess free will, the ability to judge reality and to choose one course of action over another. Know that virtues and morality are the only navigators who can take you where you want to go-others may offer a shortcut, but despair and destruction are the only places they end up. Be honest enough to admit the virtues you lack, and realize that through your own free will, you possess the ability to mold and create yourself in the image of your ideal.
An amazing thing happened when I really, truly, absolutely took responsibility for every condition of my life: I discovered self-esteem. Real self-esteem is not the aggressive posturing of clowns you have been taught to hold as evidence of self-confidence; they seldomly even possess a real 'self' in which to hold esteem. Self-esteem is self-reliance. Self-esteem is the act of believing yourself worthy of whatever happiness you desire to achieve--and the knowledge that to be worthy of it, it must be earned. Whether it is your self-concept or your fortune, you can only value that which you earned for yourself; everything else is largely meaningless.
Self-esteem is earned. It is earned by having goals and being your own ruthless, impervious judge of the extent to which you have sought to achieve them. Believe me, it is a price worth paying, no matter how hard and how awful it gets.