COVID-19 ravaged the United States and the rest of the world in a similar manner as a Category V hurricane would, leaving no one safe in its wake. Unlike a hurricane though, where appropriate provisions and supports are possible and past experiences can help to prepare, how do you prepare for something Volatile, Uncertain, Complex, and Ambiguous such as a worldwide pandemic? Imagine having your high school graduation and prom ripped away from you with little to no warning. Imagine being a 40+ year professor and being told that "you are now going to teach hybrid with some students in the class and some students online, " or imagine that you were accepted into the 2nd most prestigious Ph.D. program in the United States and dream of being a professor and look for those face-to-face mentoring opportunities on campus. This book addresses the lived experiences of many throughout the onset, duration, and the after-effects of the COVID-19 pandemic, and helps prepare readers for the never ending storm ahead. Our book offers guidance from leaders from different walks of life. We visit with a pastor who had to "get creative" to combat the pandemic, examine how school board members have interacted with parents and other community stakeholders, hear from a current superintendent in a large school district in Maine, and other stakeholders impacted by COVID-19. Our message is cautious, yet optimistic, to prepare the reader for life in a VUCA world.