Introduction Despite being recognised as a key physician competency, leadership development is an area of improvement especially in undergraduate medical education. We sought to explore the lived experience of leaders who served in elected, representative roles during their time in medical school. Methods We used a hermeneutic phenomenological approach to uncover the essence of the medical student leader experience. From late 2020 to early 2021, we interviewed 12 medical residents who served in elected leadership roles from 2015 to 2019. Each participant graduated from a different Canadian medical school. We deliberately chose a limited and historic time period in order for participants to be able to reflect on their past experiences while accounting for differences in the medical student leadership experience over time. We then engaged in a reflexive thematic analysis to generate the final themes. Results We identified the following five themes: (i) living with busyness, (ii) the role of faculty mentorship and support, (iii) competing demands of leadership, (iv) medical student leadership as enriching and (v) creating better physicians. Though demanding, medical student leadership was found to be rewarding and particularly key in the development of a more well‐rounded physician. Furthermore, being well supported by faculty contributed to an overall positive leadership experience. Discussion In addition to describing the hardships and rewards that make up their experience, this study suggests that medical student leadership can enhance core physician competencies. The findings also support the notion that faculties have an important role to play in supporting medical student leaders. .@HG_Annan, @VDoTweets & @ammacleod take a deep dive into the lives of medical student leaders, exploring the successes and challenges of their experiences and the role medical faculties play in shaping them.