Max Simkin repairs shoes in the same New York shop that has been in his family for generations. Disenchanted with the grind of daily life, Max stumbles upon a magical heirloom that allows him to step into the lives of his customers and see the world in a new way. Sometimes walking in another man's shoes is the only way one can discover who they really are.

Jaded 74-year-old reptile Leo has been stuck in the same Florida classroom for decades with his terrarium-mate turtle. When he learns he only has one year left to live, he plans to escape to experience life on the outside but instead gets caught up in the problems of his anxious students — including an impossibly mean substitute teacher.