The problem for me is that the very idea of good self-esteem seems like an attempt at willful self deception in order to be happy. The reasoning seems to go like this:
1. People want to be happy.
2. People who see themselves as bad or deficient are not happy about their badness or deficiencies.
3. Therefore low self-esteem causes unhappiness.
4. So if we want people to be happy we need to give them higher self-esteem.
5. We should, therefore, convince unhappy people to see themselves as very good/beautiful/talented/intelligent - basically as possessing the qualities they value people for having.
You will have noticed that this is bad reasoning. Statement 3 is guilty of non causa, pro causa; it treats a common corellative of unhappiness as the cause of unhappiness. There is no compelling reason to conclude that seeing myself as very bad should cause me unhappiness. At least not unless I want to be good, and improvement is an impossibility. And we have no reason to think that improvement is impossible. As a Christian I believe that perfection is ultimately guaranteed. I get to be perfect some day, so why worry about how far from perfect I am right now? In fact, shouldn't my awareness of my current imperfection give me some happiness when I realize that my God (whom I love) loves me even the gross way I am? If I were perfect I would be able to say something like "well of course God loves me, who wouldn't love this" and I could say it without any arrogance or pride. If I were truly as glorious as I hope to one day be, then any scrupulously honest self appraisal would have to conclude with perfection. I don't think that that would (or will) diminish my appreciation of God's love but isn't that love even more apparent when I see that "while we were yet sinners, Christ died for us"?
I think the pop-psychologists have missed this. What do they do with someone who is genuinely untalented, physically ugly (by their own societies standards), not especially talented at anything, generally unkind to everyone around them, and effectively lacking in anything we generally consider lovable? How do you tell someone to look in the mirror and find something wonderful about themselves when there is nothing especially wonderful about them, or at least nothing that falls under the modern rubric of value? I know, generally we haul out the myth of balance to avoid even thinking about this question but when you look yourself in the mirror, the myth will fall to pieces.
Or even if a person does have something this world values; say they are especially beautiful. Anyone who is honest with themselves can easily pick out a dozen flaws, imperfections and "unlovable" qualities in their character. The pop-psychologists tell us to pretend they aren't there. Even Christians tell me, "but that's not really me". Really? Then who is it? If I am not the one who has all those terrible thoughts about my closest friends, who is it who does? Sure, I hope to get beyond all that someday but today certainly isn't that day. Today I am spiteful, envious, lustful, discontent and selfish. Pretending otherwise can only last so long. All lies, even self-lies, collapse in the end. All self-esteem based on self-delusion is nothing but a house of cards under the hurricane of life. Simple reality must ultimately blow the pretty bandages off of all our festering wounds.
And then where will we be?
But I don't think that happiness or, even more importantly, Joy has to be built on high self-esteem. I think that the more honest, more real, more true our self-image is, the stronger a foundation it will be for Joy, and even for happiness. When I can look at myself as myself and see first that I am infinitely valuable simply because I exist (a quality I share with everything and everyone else) and then that I am nonetheless weak, twisted, often evil and ugly - when i can see all of that and know that I am loved, then how could anything shake my joy?
What worries me is that our culture, Christian and secular, seems to be losing it's ability to love through evil. There is an old Christian platitude: Love the sinner, hate the sin. Some people like it, some people hate it. I have opinions but I don't think they matter much since I don't think the phrase means anything to us any more. Nobody loves sinners. At least, nobody loves sinners as sinners. When we make any attempt to love sinners we seem to invariably begin by pretending that they aren't sinners. We only love sinners as saints. Which is why relationships fall apart when reality inevitably forces us to see the sin. When we just can't ignore their faults any more, we have not tools, no practice, no experience and only one example in the priceless skill of loving the unlovable.
Jesus said that they will know we are his followers by the love that we have for one another. Doesn't that mean that our love needs to be a new kind of love? Doesn't that mean that our love has to be a love that is impossible to those who haven't decided to follow Him yet? Is it possible that He was talking about the kind of love that He has for us? Love that loves such a worm as I?