This book presents 20 portraits of urban leaders whose personal journeys, from our perspective, illuminate a possible syllabus for sustainable city futures. These 20 personal stories are but a representation of conversations we have had with many inspirational city leaders over the years, that have stuck with us long after they occurred. We share these loosely structured pieces, gathered from 60- minute interviews, letting our interviewees responses to provide direction, leaving thoughts unfinished and some topics and questions unanswered.