Analysing the triad understanding-personal identity-education in three different contexts (scientism, historicism, hermeneutics) make it possible to investigate the kind of thinking that is emphasised most in each context. The implications of thinking to educational practice are stressed at each level of interpretation. The chief shortfalls in the first two contexts are reviewed, together with their restrictive consequences for how education comes to be understood and practiced. The hermeneutic context recognises the primacy of interpretation and pre-understanding in all human understanding. Because of this it acknowledges the interplay that is invariably active between understanding and personal identity, and between both of these and what it means to educate. This third - hermeneutical - context is therefore offered not as any kind of final word on educational matters, but as a more appropriate and inclusive context in which education as a practice might be thought about and bettered.