The importance of reflective pedagogy is widely acknowledged in HE and is a cornerstone of the helping professions curricula, enhancing students' self-awareness and reflective skills. The literature emphasizes the virtues of reflection for the students' personal and professional growth but insufficiently addresses the emotional pain entailed. To contribute to filling this gap, we examined how 103 students of social work and educational counseling experienced growth and emotional difficulty during a three-stage Life Story Reflection (LSR). Content analysis of the students' written reflections upon completing the LSR and interviews conducted a year later revealed a strong sense of personal and professional growth, coupled with emotional difficulties. These two were perceived as intertwined components of the LSR, where feeling pain is necessary to develop personal and professional identity and skills. We discuss the implications for understanding students' autobiographical reflection and offer practical recommendations for implementing LSR in HE.