In this paper, we criticize what we dub the “pruning view” of self-constitution, championed widely by philosophers, mainly though not exclusively in the Kantian tradition, and instead defend an alternative view inspired by psychoanalysis. We argue that normative assessment comes much too early on the pruning view, so early that it interferes with achieving deeper self-understanding that can produce lasting change. On the proposal we advocate, self-constitution must begin with a non-moralizing attempt to truly understand why one has undesirable and unwanted propensities. We call this the “understanding first” principle. Only after deeper self-understanding has been achieved are attempts to liberate oneself from unwanted elements likely to succeed.