Jake loves school but does school love him?

Jake loves school (Mother's Day Out). He talks constantly about his lunchbox and backpack. Everytime we go to church he wants to take his lunchbox, even for Sunday morning. He is super friendly and takes a nap like a pro. But...time-out is becoming a habit. I think the combination of energy, a mischievous smile and advanced verbal skills make him a challenge. He knows he did wrong but still does it! And then looks so cute afterwards that it's hard to be upset. We're searching for the right technique to teach our charmer how to obey!