One could argue that while the younger workforce is declining, the older adults could constitute growing economic potential through the role of entrepreneurship. The expectation is that more and more people will continue to work longer and a section of these are self-employed. Taking the economic necessity out of the equation ((state)pension), the question is: why do people decide to maintain an active economic role in society after having worked for all their active economic life? This chapter uses a qualitative approach to investigate how and why people aged 50 and over become self-employed and focuses on whether entrepreneurship adds to feelings of well-being for older entrepreneurs. The pursuit of well-being through entrepreneurship is a relatively new field of research in economics. Most studies agree that most motivations for entrepreneurship are non-pecuniary in nature and often are related to outcomes of increased well-being. This is true for entrepreneurs of all ages but the emphasis or importance given to certain motivations varies with age. How individuals decide to become self-employed depends on both context and characteristics. We study the decision-making process using the theory of planned behaviour which states that the intention to execute certain behaviour is influenced by three determinants: (1) the attitude of a person towards certain behaviour; (2) the subjective norm an individual experiences; and (3) the perceived feasibility. We discuss how these three determinants help generate higher levels of well-being for the entrepreneurs at this stage of their lives. We find that the older self-employed are experiencing higher levels of well-being as a result of their decision to become self-employed, due to increased personal control, flexible working hours and/or dream fulfilment. First, the participants in our research have a positive attitude towards becoming self-employed. Second, they are influenced by their social environment, mostly in the shape of family members, former employers and professional networks, in the way the grey entrepreneurs reflect on their own self-employment. Third, their risk acceptance is high, but the actual risk is usually low because they are often not fully dependent on the income from the business. This study provides a better insight into how we can motivate people to stay economically active longer and increase their perceived well-being.