Transitioning a business is never easy under the best of circumstances; having a family succession plan is even thornier. After all, you are entrusting your life’s work to people who, years ago, may have 1. Stolen your boyfriend (or favorite party dress or Johnny Mathis album), 2. Crashed the station wagon while carousing after a high school football game, or 3. Been the family egghead who played Etch-A-Sketch at the dinner table and seemed to relate better to the dog.