Obstetrics is a unique specialty due to the nature of caring for two patients simultaneously during a very emotionally charged period in a person’s life. There are multiple situations that can result in having to make challenging decisions which can have life-altering consequences for your patient and/or child. This chapter reviews some of these clinical scenarios, reviews the tenets of decision-making while avoiding common pitfalls, and discusses tips to help new physician attendings to deal with the stresses of making critical decisions.