Failing is a neglected topic in career development theory and counselling practice. Most theories see failing as simply the opposite of success and something to be avoided. It is contended that the Chaos Theory of Careers with its emphasis on complexity, uncertainty and consequent human imitations, provides a conceptually coherent account of failure in career development. The benefits of failing are outlined. The counselling implications of failure and ways for it to be addressed and utilised with those confronting career development challenges are also discussed.