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In this paper I present my approach to philosophical counseling, which aims at facilitating self-transformation in counselees. This approach is inspired by important thinkers throughout the history of Western philosophy who envisioned a personal transformation towards a fuller and deeper life, and whom I collectively call transformational thinkers. As noted by transformational thinkers, individuals are normally confined to narrow, rigid, superficial attitudes which are based on a limited conception of life, or what I call worldview. One’s worldview is expressed not primarily in words, but in one’s habitual patterns of behavior, emotion, and thought. The goal of philosophical counseling as I see it is to help counselees transcend their constricted worldview. The counseling process resembles Plato’s Allegory of the Cave, according to which individuals imprisoned in a narrow, dark cave step out towards a fuller reality. A case study is presented to illustrate the two main stages of the counseling process: First, an investigation of the counselee’s “Platonic cave,” or worldview; and second, an exploration of ways to step beyond its boundaries. The first stage involves analysis of everyday events, while the second stage involves searching for alternate conceptions, or “voices” that speak in the counselee’s life, and learning to open oneself to them and respond to them.