The future of careers is predicated on uncertainty as the pace of technological, societal and organisational change continues to accelerate resulting in the emergence of alternative career structures and the fading of clearly identifiable career paths. A successful career in the future will be characterised by a person’s ability to manage the uncertainties they experience and craft their career accordingly. In this chapter we move beyond the historical narrative of work as a factor of production and argue instead for a human-design approach centred upon the individual and their relationship to work. Focussing on the careers of professionals and drawing on the motivational framework of the philosopher Kenneth Burke (1945), we explore the future of careers through five fundamental questions: (1) Who are my people? (2) What is my contribution? (3) Where is my place in this world? (4) How do I adapt to constant change? (5) How do I find meaningful work?