When you are picking between the four activities the Sun gives you after Breakfast, Say "Let's catch that runaway train!" and head to that room
Click on the Sleeping Bridge Stack and have him stick out his tongue to create a bridge. You will notice the Creature you are rescuing in your train is holding on to the tracks. Once it has let go, the train starts rolling down the mountain, and that's when you can quickly click the Bridge Stack and have the bridge retracted causing the train to fall when it gets there.
You have now disrupted Shay's daily routine.