Ihad been teaching for 26 years when COVID-19 brought some aspects of my life to a hard stop and added new challenges to my teaching and personal life. This disruption forced me to create new routines to maintain my physical and mental well-being. One strategy was a return to mountain biking. An aspect of biking I had always found rejuvenating was the rhythmic movement of my legs. This rhythm, paired with time in nature, opened my mind to reflection. As I rode along trails, I realized that the resiliency I needed to traverse varying challenges on my bike was directly transferable to my life as a teacher. I realized that educators, in leadership and the classroom, need six mindsets to build the stamina and balance necessary for a career inevitably filled with roots, rocks, and hard trails partnered with successes and joys.