Caillou (1998)

Season 4: Episode 6

With training wheels on his bike, Caillou is having trouble keeping up with Sarah. After imagining himself riding in a real grownup bike race Caillou decides he's ready to try riding without his training wheels. It proves to be harder than he thought, however, and he quits in frustration. Daddy explains it's okay to wait until he's really ready. He goes back to his training wheels and the next day Sarah shows up on her new roller blades - now she's travelling at his speed.