This paper is an explication of the conceptual underpinnings of a new, narrative career counselling method: fluttering-hope. The method presents a new approach to addressing repetition compulsion, a condition characterised by repeated career-destructive behaviour and experiences of failure. Fluttering-hope is formulated on the basis of the chaos theory of career (CTC), a theory that explicitly acknowledges failure as a natural event in careers. A transtheoretical argument links failure, optimism, hope, psychodynamics and CTC concepts of attractor and shift. Repetition compulsion is posited as a pendulum attractor and fluttering-hope is posited as a source of perturbation that may induce shift. The method takes a gentle approach to repetition compulsion, and regards it as a psychological mechanism to be treated with great care in career counselling. The paper includes recommendations for future research into the CTC, fluttering-hope and mathematical modelling.