A primary tenet of Pryor and Bright's Chaos Theory of Careers is that our world is full of change and unpredictability. When it comes to career development, rather than relying solely on good planning, one should accept and embrace unexpected changes and think creatively about possibilities. Although the Chaos Theory of Careers approach to counselling is logical and relevant to the real world, it may not be applied easily to clients with high levels of anxiety and low tolerance of uncertainty. The current paper explores the challenges of providing chaos career counselling to highly anxious clients. Borrowing concepts from a cognitive behavioural theory model for generalized anxiety disorder, this paper suggests several techniques from the cognitive behavioural theory literature that may facilitate chaos career counselling for anxious clients.