Entrepreneurship can be a solution to the dilemma: “Labour is a form of education, a way of ensuring existence, gaining autonomy, a physical and mental training, a way of oppression, a form of occupational therapy, all together or …none of the variants listed?” Depending on the reference field and the perspectives offered by different specializations, work is defined as a physical or intellectual action, which develop material and emotional satisfactions. Especially in closed environments, it is practiced as a form of occupational therapy (ergotherapy), because it ensures a sense of usefulness, helping to maintain somato-psycho-emotional health. The schoolmasters highlight the formative values of work for students: evaluate the native skills and abilities, lead to the discovery of new unknown interests and talents, support the student in his perfection by inoculating the ideas of responsibility, order, discipline, etc. Before 1989, in detention environment labour was mandatory, but now, labour is an optional right. The two perspectives are diametrically opposed, and the issue was addressed only from the perspective of reduced job supply, both during detention and after release. There are few publications with strict reference to this topic. In general, the social reintegration of post-execution prisoners is addressed. At this moment, the main problem highlighted is integration/reintegration on the labour market, as the main facilitating step of maintaining the accumulations during the detention period and a primary factor for avoiding the recurrence. However, those who have served a custodial sentence do not have a "ticket" to the labour market. To be known and solved, the situation should be addressed continuously: prevention before detention, education/re-education/training / retraining during detention and placement on the labor market / retraining immediately after release.