Annually, there are school counseling specific counselor educator positions that remain unfilled. There is a need for more counselor educators with school counseling backgrounds. This grounded theory provides a model of the process by which school counselor educators decide to enter academia and what keeps them in their positions, based on focus groups with 32 participants. Results showed the reasons for leaving school counseling, what factors promote entry into school counselor education, and what keeps school counselor educators in that role. Implications for counselor education are provided.