Checking account woe is a term used to describe the financial difficulties that can arise from having a checking account. OVERDRAFT, with nine letters, is a situation in which more money is withdrawn from an account than is available, resulting in a negative balance. Chess, with five letters, is a two-player strategy board game in which the objective is to checkmate the opponent's king. Checking account woe can be compared to a game of chess, as both require careful planning and strategy to avoid costly mistakes.