It can be painful when a plan does not go as one hoped. A lot of thought and preparation might have gone into it. There may have been an investment of time and effort, and a fantasy as to how the plan would unfold. How is one to make sense of the disappointment that accompanies a failed plan? Looked at objectively, a plan is an estimate of sorts, an educated guess as to what should occur and how to get there. It is an attempt to predict the future, which of course is an exercise mired in uncertainty. So why are some disappointments harder to accept than others? The answer I think is not so much in the inconvenience or disruption of not having things materialize as one imagined but rather the extent to which one’s sense of self was associated with a desired outcome. The more one’s sense of self is identified with a certain outcome, the more conditional one’s self-regard. It is the loss of this self-regard or failure to attain it that produces the feelings of dejection we sometimes experience when things don’t go according to plan.