The Courageous Journey was, for the author, more than an official state endorsement for the professional position she holds as a district superintendent. It was a personal journey that gave her far more than she can illustrate in her final exhibition to earn her performance-based specialty superintendent endorsement. It began in August of 2005 when, for the first time, she sat in the chair of the superintendency of her new school district. Nothing in the past had prepared her to do the job. She had knowledge (and a few good ideas) from previous positions and her administrative degree program, but bookwork and people work are entirely different. This position held tremendous responsibility. In this small rural district located at the base of Michigan's thumb area, she was to become everything--director of transportation, maintenance, personnel, food service, finance and all-round answer person. She was totally overwhelmed. That fall, she encountered the startup promotion for Courageous Journey and signed up for what would become the best education experience she has ever had. In this article, the author tells about her personal journey and what she gained from it.