Increasingly, college students struggle to find translatable meaning in their college experiences. Following a program of study and dabbling in a few extra-curricular experiences proves to be enough to graduate, but somehow some students fail to thrive in all areas of well-being once they are at work. If this disconnect is rooted to a lack of dedicated guidance from the institution and continuous reflection on behalf of the student, then mentorship may be the key to bridging the gap. The work-study environment is ripe with opportunities to draw from the student employee's dual perspective, enriching the knowledge of both parties. The mentor can encourage pragmatic growth and meaningful reflection as the mentee offers insight into the preferences and needs of today's student. Utilizing the design thinking paradigm, design solutions to personal and institutional challenges can be developed together, creating authentic, interdisciplinary understanding.