Summer in Evergreen Hollow always carried a particular sweetness—the kind that came from long evenings on the porch, the hum of cicadas, and the quiet pride of watching children chase their dreams. This year, though, the sweetness had an extra layer: Lily was spending eight weeks in Indianapolis as part of a prestigious NCAA program focused on Name, Image, and Likeness (NIL) policy development.

The opportunity had come unexpectedly in late spring. Lily’s entrepreneurship professor at ...