It’s not uncommon to arrive at the moment within a consultation when the client feels confronted by an unavoidable career crisis: leave because s/he can’t see any future staying; or stay because s/he sees no alternative to accepting the limitations being imposed by the larger system. This paper examines three cases, one up close, in which the client had come up against a wall: one providing on-line gambling, one procuring military capabilities, and one providing intensive social care. In each case there existed possible courses of action that could have provided better outcomes and made greater commercial sense, but which were nevertheless judged as beyond the pale by the existing powers. The challenge for the client is to use the crisis while not taking it personally. The paper explores the psychoanalytic basis of the walling off as a systemic defense against innovation and the challenge to leadership in overcoming it.