As an early childhood care and learning administrator or owner of a home-based child care you are juggling many financial obligations. In my experience, effectively navigating both the management of and conversations with families about children’s challenging behaviors is a commonly cited struggle for administrators in the field. Ensuring that your program can manage challenging behavior can be expensive—but, I hope to show, not as costly as not effectively managing behavior. I also note that in many of the examples, I am inviting us to think about the worst of what could happen—yes, things may not get as far as some of these examples, but they are useful for us to hold in mind as we engage in the exercise of the “What if?” on the way to thinking about possibilities.