This conversation explores the differences in how high school students, particularly boys and girls, approach the transition to college and career. Bill Priestley hosts college counselors Janet Weller of Harpeth Hall School and Colin Dunnigan of Montgomery Bell Academy in Nashville, who share insights from their experiences as college counselors at all-girls and all-boys schools, respectively. They discuss the ideal college counseling process, the nonlinear reality of decision-making, the impact of parental involvement, and the pressures students face. The conversation also touches on the importance of mentorship and the evolving landscape of college admissions.