The Möbius strip is one of the most curious shapes, and there is value in using it as a metaphor for the leader-follower relationship. The creation and exploration of a Möbius strip promotes a sensemaking process for understanding the dual leader-follower identity necessary for effectiveness in both leader and follower roles. Furthermore, the Möbius strip can help guide thinking about healthy mentoring relationships and the ideal flow between what may seem to be contrasting priorities or styles. This paper explores practical insights from research on middle managers, experience with student programming, and historical analysis of community cultures. The exploration highlights the importance of humility in leadership and surfaces a variety of questions for further consideration.