This contribution focus on the difficulties of offender reintegration by especially discussing formerly imprisoned drug users’ difficulties in re-entering the labour market. It has been found in previous research that employment has positive effects on the reintegration of offenders into society. For example, employment can lead to an increased feeling of responsibility, personal worth, independence, dignity and of having a stake in society. However, one major barrier faced by many former prisoners entering the labour market is a past history of drug use. Although the relationship between employment and crime is a relatively well-explored area of research, few qualitative studies have focused on how formerly imprisoned drug users perceive and interpret the importance of having a job and how they view being unemployed following their release from prison. This paper will present a study conducted in Sweden about how formerly imprisoned drug users perceived the possibilities and problems associated with entering the job market. The study focused particularly on how the participants perceived the situation of being without a job, whether being employed created a sense of meaningfulness and whether using drugs and/or engaging in crime was related to their periods of unemployment. Semi-structured interviews were conducted with 22 former prison inmates with extensive prior drug use. The interviews were coded and analysed using a categorical-content, narrative analysis approach. The interviews revealed that although the respondents did not regard themselves as having been unemployed, some mentioned stress during periods in which they lacked a legal occupation. The participants also talked about the importance of being committed to one’s work and described that it was not only employment in itself that was important, but also being able to value or appreciate their employment. Most respondents argued that they had never been dismissed from work because of their drug use, but descriptions of workplace deviance were common in the interviews, e.g. stealing, selling drugs, burglary, using drugs at work. The study revealed that the respondents lack an identity as either unemployed or employed, and although all of them stated that they were neither committing crimes nor taking drugs, it appears that they have retained an identity as criminal and/or drug users, which may become a problem when they apply for work in the future.