The purpose of this chapter is to describe the set of behaviors within organizations referred to as political blunders, or insensitive acts that get workers into conflict with their manager and organization, and can damage their career. Blunders are also referred to as committing a faux pas, committing a gaffe, or “putting your foot in your mouth”. The theoretical basis for understanding why blunders occur centers on the theory of emotional intelligence, and more broadly the theory of self-defeating behavior. The latter refers to activities or attitudes that work against one’s best interests even when the individual appears to have the resources to avoid such behavior. Effective tactics for recovering from political blunders are based on knowledge of conflict resolution, including the effectiveness of apologies as a way of being forgiven for the blunder or blunders. The career-retarding blunders described are (a) public humiliation of others, (b) violation of company codes of ethics, (c) out-of-control avarice, (d) disseminating negative messages and misdeeds electronically, (e) bypassing the boss, (f) being revengeful and hostile during an exit interview, (g) indiscreet behavior in private life, and (h) conducting an office romance improperly. The blunders leading to embarrassment and minor setbacks described are (a) being politically incorrect, (b) displaying impatience for promotion, (c) gossiping about taboo subjects, (d) attacking sacred cows, (e) refusing to take vacations, (f) rejecting business social invitations (g) wearing overly sexy clothing, (h) inappropriate consumption of alcohol, and (i) insensitivity to public opinion. A recommended way of recovering from a blunder is for the organizational member to admit he or she made a mistake, apologize, and then refrain from committing the same blunder again.