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You may be lacking self-esteem because of previous mistakes you've done in your life. They make you think that you are flawed and are bound to repeat them. But we learn on our mistakes (at least we should), so only the fact that we did some mistake does not mean we will repeat it. You should not see your past as a measure of your current state, it is a measure of what you were before and if you learned your lessons, it means that you are now a better person than you were, and can live a better life than before.
I'm very concerned that rational people who have apparently mastered the Way spend their time arguing on irrelevant matters with users here rather than being in line with their utility function and purpose.
So a part of my future research is how to figure out how to communicate with high-IQ individuals here to unlock their potential and improve their reasoning.
So... you are going to spend your time arguing with users here, but you've come with a reason for it, so it doesn't seem irrational? ;)
I would recommend reading 'Undoing Depression' of Richard O'Connor. Specifically, there are good ideas about work and motivation in ch.15, but I would recommend reading the whole book anyway for the big picture.