Principal Durbin takes it upon himself to help Jack advance his book with an appearance on Toledo's morning TV show but lets his five minutes of fame get the best of him; the other teachers lead a competition within the Young Entrepreneurs Club.

As the school prepares for winter break, Jack tries to record a lecture on Thoreau's transcendentalism as a way into the University of Wisconsin's philosophy department; frustrated and unable to finish the video, he falls asleep and has nightmares.