This chapter examines experiences of entrepreneurial loneliness in the 19th century. Positioning loneliness as a product of absence, I use a case study of John and Elizabeth Shaw to explore how entrepreneurial activities generated loneliness in my subjects’ lives and how they reacted to and attempted cope with such experiences. Against a background of quickening industrialization and distanciation, entrepreneurial families found themselves negotiating changing understandings of male and female roles, particularly as they played out in public and domestic settings. John and Elizabeth experience loneliness as a painful emotion and longed for each other’s presence in the setting of the family home—a home that John’s entrepreneurship frequently took him from. Nonetheless, it is hard to identify a uniquely entrepreneurial experience of loneliness.