How should policymakers respond to the risk of technological unemployment that automation brings? First, I develop a procedure for answering this question that consults, rather than usurps, individuals’ own attitudes and ambitions towards that risk. I call this the insurance argument. A distinctive virtue of this view is that it dispenses with the need to appeal to a class of controversial reasons about the value of employment, and so is consistent with the demands of liberal political morality. Second, I appeal to the insurance argument to show that governments ought not simply to provide those who are displaced by machines with unemployment benefits. Instead, it must offer re-training programmes, as well as enact more general macroeconomic policies that create new opportunities for employment. My contribution is important not only because it helps us to resolve a series of urgent policy disputes—disputes that have been discussed extensively by labour market economists and policymakers, but less so by political philosophers—but also because my analysis sheds light on more general philosophical controversies relating to risk.