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After analytic training, graduates position their newly acquired identity as “psychoanalyst” in the context of their broader career, contemplating whether to start new analytic cases, adapting their new knowledge base to psychotherapy practice, and deciding how to focus their professional and personal interests going forward. Using questionnaires and interviews, the Columbia Postgraduate Analytic Practice Study (CPAPS) has prospectively tracked the career trajectory of 69 of 76 graduates (91%) from the Columbia University Center for Psychoanalytic Training and Research since 2003. In this paper grounded theory is used to identify developmental themes in interviews with analysts who have been followed for at least ten years. Recent graduates are negotiating the following challenges: developing a sense of competence, navigating relationships with colleagues and former supervisors as situations change and roles shift, transitioning into becoming mentors, and balancing the competing responsibilities of professional and personal life. Disillusionment about aspects of training, analytic practice, analysis as a treatment, institute politics, and the field in general emerges as a stark reality, despite a high level of career satisfaction. Educational recommendations include making career development opportunities available and providing a realistic view of both practice realities and expectations of analytic treatment outcome.