In this chapter we examine who probation workers are. We look into their backgrounds and explore what motivated them to consider the probation service as a career choice. We track their routes into the service and their progress through different training frameworks. The probation workers we interviewed come from a variety of backgrounds, although there are identifi­ able groupings, that we have called: ‘lifers’ (a term first coined by CO8 and comprising predominantly baby boomers,1 first­ generation university­ educated, idealistic people, who joined the service at a young age); ‘second careerists’ (often having had previous careers in teaching, the armed forces, the police, health and social work); and ‘offender managers’2 (more recent recruits with varied backgrounds, for whom probation is one of a number of jobs they expect to have throughout their working lives). To illustrate this embryonic typology, we present three individual pen portraits.