The current political climate has encapsulated what we have longed recognized: that unpredictable—even outlier, low-probability events—happen. This unpredictability and volatility, when mirrored on a micro level in the lives of parties to a conflict, can be similarly jarring. Faced with such stresses, some parties to conflict seek to regain a measure of control and autonomy in an otherwise chaotic moment. In mediation, a vital aspect of the role of the mediator entails reality-test decisions. And a facet of that effort is to contemplate with the parties various reasonable hypotheticals. This is not merely an attempt to use one’s crystal ball to foresee the future but an opportunity to help craft a flexible and durable agreement. When we work with parties we also discuss likely shifts in their lives, whether personal or financial, that may test the implementation or sustainability of various decisions. And, as with substantial changes in the world order, adjustments must be made. Writ small, in personal contracts, how can mediators help parties achieve their mutual and thoughtful goals while the ground beneath them has shifted unpredictably?

The extent to which we explore with parties various eventualities depends in large part on their dynamic. Some parties are cooperative with each other and do not wish to be locked into a particular way of problem solving, relying instead on deeply shared values and goals; others are looking for a blueprint to guide them should conflict arise with a change in circumstances. Still others, harboring deep mistrust or differing perspectives as to how to problem-solve, need predictability and a codification of their maximum exposure in order to come to final agreement. A prime example of this process comes into play in the mediation of prenuptial agreements when couples, independent and self supporting, are eager to waive spousal support rights and obligations. We may push back: What happens if one of you becomes ill? If you have a special needs child? Wish to retire early? Life happens in all sorts of ways, good and bad, that we try to anticipate.