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Founding a program is never easy, especially during a global pandemic. However, this was the predicament I found myself in as the President of the student organization, Stepping Out, in the spring of 2020. However, this predicament allowed me to help pioneer a program that helped lay the groundwork for other virtual volunteering programs at the Johns Hopkins Medical Institute (JHMI). Through this reflective piece, I want to share my observations on this event. Additionally, after almost two years as President of Stepping Out and three years as part of the elected board (E-board), I also would like to highlight what I have learned about leadership and providing clinical community service during a global pandemic. By the time you are done reading this, you will learn about the considerations that have to be made when creating and leading a virtual volunteering program, as well as insights into mistakes I made and how to avoid them. Finally, it is my hope that this piece will prove to be useful for future student organization leaders the next time a global pandemic comes around, or at the very least, be an interesting read.