Research has shown that encouraging choice, self-initiation of behavior, and personal responsibility leads to both cognitive flexibility and self-esteem (McGraw & McCullers, 1979; Deci, Schwartz, et al., 1981). An appreciation for the positive impacts that peer tutoring can have on students' growth, confidence, and academic achievement, coupled with an awareness that many students hesitate to ask for help, led to the creation of a tutoring scholarship at Indiana University South Bend. Self-Determination Theory informed the formulation of the scholarship's essay requirements, with tutoring assessment guidelines and indicators of academic progress providing the baselines for service usage and academic outcomes.