Sick of being pushed around by others and being a doormat, Fluttershy takes a class on assertiveness taught by self-help guru Minotaur; Iron Will. Fluttershy is thrilled with her new found confidence but when her concerned friends Rarity and Pinkie Pie confront her about her recent behavior, she mistakes their concern for an attack and retaliates by insulting them. Distraught by the upset she’s caused her friends Fluttershy locks herself in her cottage.
Concerned about her, Pinkie Pie and Rarity come by to try and coax her out by explaining she doesn't have to be a bully to be assertive. Fluttershy must learn that there is a time and place for being self-assured, and it doesn’t necessarily have to involve being bossy and mean. This concept is suddenly tested when Iron Will pays her a visit demanding payment for his services…