When a society is undergoing transformational change, it is a challenge for all involved to step outside their immediate context sufficiently to evaluate its implications. In the current digital revolution driving Industry 4.0, the pace of change is rapid, and its scale and complexity can inhibit a proactive, rather than reactive, response. Yet if it were possible to return to the first industrial revolution, armed with twenty-first century knowledge and historical perspective, planning for a healthy society and the future of work could have been very different. This chapter aims to support educational leadership in the development of proactive strategies to respond to the challenges and opportunities of Industry 4.0 to inform the future of work, industry, and society. This is framed through the lens of product design, with its unique position at the nexus of engineering and the humanities, and directly tied to changes affecting manufacturing in the fourth industrial revolution.