Rules of the Road opens with 16-year-old Jenna Boller skillfully using the sliding ladder at Gladstone’s shoe store in Chicago to retrieve boxes of shoes for her customers. She describes herself as a “shoe professional.” Jenna knows how to connect with customers, making each one feel special, regardless of how busy the store is. She has ways for dealing with tricky situations, such as a “breath-holding contest” for fussy children (2); She gives difficult kids a stopwatch and the promise of cool laces for the one who holds their breath the longest. Jenna loves her job, and she knows she is good at it. She exudes confidence on the shop floor and never doubts she will end up with a happy, satisfied customer. This confidence does not extend outside the shoe store. When Jenna was a sophomore at high school, she gained 17.5 pounds, was demoted in the basketball team, dropped off the honor roll, and was bullied. “I just limped through sophomore year” (6). At Gladstone’s, she feels successful, helpful, and needed. She says people look to her instead of away.

Jenna’s boss, Murray Castlebaum, is an accomplished shoe seller who appreciates quality and good service, traits he instills in Jenna during her training.