The aim of this study is to better understand how entrepreneurs become employers. Taking a phenomenological position, my research uses a co-creative methodology to explore transitions from entrepreneur to entrepreneur-employer. Job creation is commonly cited as a benefit of entrepreneurship (Birch, 1979; Acs, 2006), yet little is known about the transition to entrepreneur-employer. Recent estimates highlight that many UK enterprises are classified as non-employing businesses, comprising the founder only (ONS, 2020). This suggests that while a high proportion of individuals enter self-employment, growth presents a significant challenge for many (Coad et al., 2017). Extant research investigating the entrepreneur to entrepreneur-employer transition is predominantly functionalist, reinforcing commonly held beliefs that entrepreneurship is a desirable economic activity (Dvouletý, 2018). In response, I sought to apply a qualitative approach. Using Interpretative Phenomenological Analysis (IPA) as a guiding framework, I explore the lived experiences of six female and four male entrepreneur-employers in South Wales. My contribution to the entrepreneurship field is twofold. Firstly, my findings reflect an uglier reality to job-creation than is readily visible in the mainstream entrepreneurship literature. Perceiving it as a double-edged sword, participants juxtaposed common entrepreneurial narratives against their everyday realties. Becoming an employer introduced a level of relationality, exposing participants to systems demanding conformity rather than entrepreneurial diversity. Second, methodologically I demonstrate how the use of a co-creative method is a valuable tool for accessing complex and nuanced entrepreneurial experiences. Participants universally expressed frustration at being suspended in what I interpret as a liminal state. Drawing on relevant literature, I theorise that this is particularly felt within neoliberal post-industrial contexts. I conclude that, for my participants, negotiating the gap between mainstream entrepreneurial narratives, and their lived entrepreneurial experiences, was a significant factor in moving beyond the critical entrepreneur to entrepreneur-employer transition.