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How do we boost our son’s self-esteem?
It sounds as though you are already doing the right things – and are even aware of the fact that you can overdo praise and encouragement.

I wrote an article for this website titled “Praise: Serve in Small Portions” that I urge you to read. In it, I quoted two mothers who had expressed their conviction that praising a child for every act of good behavior was actually harmful and had led to either a sign of anxiety or a real tantrum when praise was not forthcoming every time. When that happens, I think it is a sign that the child is becoming dependent on adults for evidence of whether a given act is acceptable or not and is failing to develop his or her own ability to judge praiseworthiness. In the long run, it’s that internal evaluation that is most meaningful.
Dr. Bettye M. Caldwell Ph.D. Professor of Pediatrics in Child Development and Education