Private security work can be a brutal world of short-term contracts, exploitation, and under-regulation, where the imperative of profit is expected to trump collective notions of military brotherhood. Why then do so many demobilized soldiers turn to it as a vocation? While a rich body of work has revealed the vulnerabilities of demobilized military life, ethnographic investigations into how contractors experience and make sense of precarity are less common. Drawing on fieldwork with military veterans of European descent working and living in East Africa, this article argues that a central, yet underexplored, feature of contemporary security work is colonial nostalgia. Some contractors read the travelogues of colonial adventurers, while others trace their family genealogy to ancestral colonial frontier soldiers. A few even write their own memoirs in similar fashion. Writing, reading, and living the colonial past through this contractor canon serves several present-day functions. First, the parallels between risk-taking colonial adventurers and the kind of rugged individualism associated with homo economicus masks the tensions and fissures that emerge from soldiers’ discharge from the military and subsequent remobilization as privatized contractors. Secondly, colonial nostalgia forms part of a larger political critique of Western military interventions, of which many of these contractors experienced first-hand. Here, private security work is imagined as replicating an older, more effective tradition of frontier soldiering that is rooted in a logic of settler-colonialism. Finally, fantasies of a colonial past feed into contractors’ attempts to market themselves to clients and to organize their everyday work.