Growing, learning and developing are lifelong endeavors. While the time on a calendar can be linear in nature, the process of maturing emotionally does not follow this same trajectory. Ordinary development is anything but linear and predictable. Times of growth and understanding can be followed by moments of withdrawal and regression. Sometimes it is precisely withdrawal and regression that spur one on towards new developments in life. There is a forward to backward, left to right, up and down and all-around-ness in growing up. Growing presents a mixture of emotions that can often feel contradictory. For instance, an adolescent moving out of the house to attend college may feel both apprehension with the responsibility and excitement with new freedom. A young child may feel momentary satisfaction in learning to potty train and simultaneously feel worried about the jump in independence. A retiring adult may feel the liberty of an uncharted path together with the regret over opportunities lost. With gains there are losses and this creates ambivalence. Learning in life is shaped by one’s relationship to experiences, circumstances, mistakes, uncertainty and ambivalence. Reflecting, reaching out to others and reconsideration create the opportunity for learning and flexibility. Sometimes, mistakes get confused with failure and one’s self-criticism can get in the way of making use of mistakes. Sometimes, uncertainty is overwhelming and accumulating knowledge gets confused with growing into one’s own. For example, a highly intelligent and verbal child may also have trouble metabolizing his upsetting feelings and throws tantrums; or a recent college graduate may expect herself to be a competent professional who always gets it right in a field in which she is just entering. Faced with these ordinary yet complex dilemmas, it can be difficult to sustain confidence in the growing process. This is especially true when despair has set in over a long period of time. In these stages, relationships with important others are integral to regaining a foothold in growing up. Parents, partners, teachers, school counselors, therapists are all different kinds of such relationships, instrumental in confirming the idea that development is a tenacious and satisfying struggle.