Desistance is generally presented in a positive light, with themes of ‘making good’ and generativity recurring in the literature. This article reports on two qualitative studies exploring the desistance journeys of two different groups of ex-offenders, drawing attention to the pains of this process. It examines the possible consequences of these ‘pains of desistance’ and how they are linked to three spheres of desistance: act-desistance; identity desistance; and relational desistance. The attempt to achieve act-desistance often led to the pain of isolation for our interviewees, while the clash between the need to achieve identity desistance and a lack of relational desistance (especially on the meso- and macro-levels) meant that they suffered the pain of goal failure. The pains of isolation and goal failure combined to lead to the further pain of hopelessness. Those interviewed were indeed ‘going straight’, but taking this path led many to a limited and often diminished life.