Purposefully Negative Talking from My 5-Yr-old Son

My stepdaughter does this because she thinks she can't do it and she's afraid of failing. For example, she really wanted to sew a skirt for her dolly (she's 8) and couldn't wait and couldn't wait. She stitched two stitches and then declared it was "boring" and "she didn't care anymore." Well I knew she did care! She will declare things "boring" or she's "not interested" if she thinks they are too difficult. Sounds like your little 5-year old might be similar in personality!

Ignore the negative talk and don't try to handle what he says. If he says "it's boring" and you try to show him how exciting it is he won't respond because you're not handling the right problem. He doesn't think it's "boring" he thinks it's too hard or that he might make a mistake. Instead try to see what he is really worried about and give some encouragement.

When my SD said her sewing was "boring" I said "you're doing so good! I think you're the best at this, certainly better than other girls your age! Look at what you did so far! Is there something you're having trouble with? Can I show you again?" And what do you know, I showed her again how to do it and suddenly she was all smiles and eager to get sewing again.

(My SD is also a wise-cracker and a clown. She does this when she's unsure of herself. She tries to be funny to draw attention away from the fact she can't do XYZ. It's hard to see this because she LOOKS like she has a lot of self-esteem because she's talking and laughing and being the center of attention. In reality, she doesn't, hence the clowning around.)

Good luck!

Check out the helpful book How to Talk So Kids Will Listen, and Listen So Kids Will Talk. It gives extremely practical advice on how to respond to kids by not denying the feelings they have. Amazingly, children can often resolve their own emotional issues once they believe you have really listened to them. You can read part of the book here: http://www.amazon.com/How-Talk-Kids-Will-Listen/dp/038081....

There are also recent studies on children's motivation that show that when we label our kids as "great" or "smart/strong enough to do that," or overwhelm them with our own wishes for their success, it tends to turn them off. Kids really do need the space and time to determine what is important to them and how much effort they are willing to give.

I wonder whether the teacher, in trying to motivate him, is suggesting something like "Of COURSE you want to do that! You were always SO GOOD at it." That would be demotivating on two counts: disregarding the child's expressed feelings as if they don't count, and setting a goal that he feels unable to fulfill. He may be afraid that he must surely let the teacher's high opinion of him down at some point, so why not get it over with?

See if you can use the techniques offered in the book to get to the bottom of his discomfort.

OOOOH he sounds like a Smart little guy who is testing the limits :) \
An exciting time for sure. Maybe you could share some Negative tasks that you have to deal with then tell him the positive of why your doing them.
"I don’t want to go to the bank :( But if I go to the bank I can put money in my savings :)"
then see if he can relate to you.
""I don't want to record the Governor’s Challenge" :( "But if i record the Governor’s Challenge I will be healthy " :)

hes playing a game with you. If you change the game he may not even notice and it could be a learning experience.

School brings on a lot of new challenges, so 5 is a tough age. In most cases they have never been asked to do any kind of schoolwork, and if they didn't enjoy something, they generally just moved on. To me he sounds like a smart kid with a good sense of humor. He may need to conform to get along, but don't push it too much. Part of me wonders if he is not being challenged, or if the classroom is too structured. He sounds like he would do better in an envirionment where he is entrusted with a little more responsibility. Sitting in a desk all day responding to commands is no way to learn. It stifles a valuable imagination. I could go on, but I think I've made my point.