A cursory reading of the literature describing yesterdays’ societies in the Stockholm Archipelago tells us that people in the archipelago heavily relied on fishing and small-scale farming for their living. With the arrival of modern industrialized society during the latter half of the 19^th century, things changed, and other opportunities to earn a living appeared. However, there were and are certain circumstances in the Stockholm Archipelago that make it somewhat inert, preventing it from taking a place in the modern labor market. Some of these have to do with its geographical location and legal frameworks, while others derive from cultural constructions among the nearby town-dwellers over the last one hundred and fifty years. The following reflections will focus on how some of these circumstances have affected entrepreneurs in the archipelago from the 19^th century up to today, and what follows is a sketch of a broad outline of the history of entrepreneurship in the Stockholm Archipelago. In addition, being aware of anachronistic pitfalls and possible theoretical shallowness, I will focus on the element of self-employment in the concept of the entrepreneur in order to be able to generalize among different kinds of entrepreneurial enterprises over time — keeping in mind that a common way to make ends meet in the archipelago has also been to work part time as employees, e.g. as customs officials and/or pilot boat operators.