There is a hidden paradox inherent in the ideal of continuing professional development (CPD) for executive coaches, stemming from the fact that the coach wishes to retain or preserve the freshness and openness of a ‘beginner’, whilst also acquiring greater robustness and resilience in the face of difficult assignments. The paradox reminds us of the ‘castle and battlefield’ metaphor of Roger Harrison: on the one hand a strong container is needed and on the other vulnerability to allow the coach to be affected and even hurt by the coaching experiences. The objective of this paper is to find ways of resolving this paradox, based on what coaches themselves say about critical moments in their practice.