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This article encompasses remarks I have made over the years at the graduation of candidates completing the Institute of Contemporary Psychotherapy and Psychoanalysis (ICP+P). On the threshold of this milestone, I focus on the importance of the connection to one’s professional, relational home, the influences that shape an analyst’s developmental trajectory, and the evolution of a personal idiom, using examples from the work of Norman Rockwell and Pablo Picasso. I draw attention to the inhibitory impact of shame on a candidate’s development.