In this chapter, the variety of old age entrepreneurship is illustrated through entrepreneurs in two different sectors: technical consultants and those involved in art and literary work. The empirical overview of older entrepreneurs is based on register data on the whole population of Sweden, as well as interviews with entrepreneurs. Unexpectedly, although the two industries are very different regarding markets, work content and formal skills requirements, the patterns of entrepreneurship towards the end of working life are similar. Basic economic security provided by the Swedish welfare system seems to mitigate some of the expected differences.