How often do we find that our expectations of ourselves and others haven’t been met? How many times do we wonder if we’re just expecting too much? Then, again, just how little should we expect, and how much disappointment can we, or should we, be willing and able to accept? Question like these have been asked and answered in interesting, provocative, sometimes rather discomforting ways, at least since the time of the Greek philosopher Zeno of Citium (circa 336-265 BCE), the father of classic Stoic belief and practice and the forefather of contemporary psycho-social therapies such as Cognitive Behavioral Therapy (CBT). Let’s take a bird’s-eye view as well as an up-close-and-personal look at ways we develop expectations and handle disappointment when expectations (inevitably) aren’t met, and how doing so can be a sustaining spiritual practice.