I remember when my daughter was in first grade. She came home one day to announce that it had been school picture day. I looked in despair at her. She was wearing her brother’s tie-dyed shirt, that not only was much too large, but also quite shabby. And a non-matching skirt.
“Luckily,” she continued, with a blissful smile, “I had on my favorite outfit.”
It’s the best school picture we have of her. Her brilliant, happy smile—because she felt she looked her very best—completely overwhelms the shabby shirt.
Self-confidence comes from having choices respected. Many decisions a five-year-old can’t be allowed to make. Respect the choices he can make. One thing I learned in 37 years of teaching is that an unwise decision a child makes is usually less harmful than a wise decision a parent makes and forces on him.