In the episode, Herman and his friend Jay decide to go skydiving with their boss, Mr. Crawford, in an attempt to impress him and advance their careers. The experience and its aftermath lead to humorous situations as Herman deals with the professional and personal implications, all while the characters representing his inner thoughts (Intellect, Fear, Compassion, and Lust) battle it out in his head. Herman also ends up writing an article about his skydiving experience.
