Many of the challenges that Willy faces are typical choices that a nine-year-old boy must make: whether to push his little sister on the swingset (and how high to push her), whether to mow the lawn, whether to wash his dad's car, and whether to take his dog for a walk or feed him. Making unwise choices can lead to various negative consequences. For instance, if Willy does not wash his father's car, he does not receive his allowance, and cannot buy an item that he will need later in the game. In addition, Willy has a score system called the Trouble-O-meter, a thermometer with "Good Boy" at the bottom and "Cadet School" at the top. Actions that annoy Willy's parents will cause the meter to increase by one level, and really infuriating them will cause it to increase further. If the mercury reaches "Cadet School", that is where Willy goes, and the game is over.