The history and development of applied sport psychology practice has not received the same attention and documentation as that of academic sport psychology. After a brief introduction to the literature on the history and professional development of applied sport psychology, some personal perspectives from consultants who have been practicing “in the field” over the last two to four decades are provided. Eleven well-known practitioners discuss how they got started, how their consulting has developed, what significant experiences they have had, and what lessons they have learned along the way. They relate their views on the progression of professional practice and what the future may hold. Finally, they offer some encouragement, cautions, and words of wisdom for fellow and future colleagues in sport psychology consulting.