In this paper, we revisit the entrepreneurship and poverty relationship under a eudaimonic perspective that brings together conversion factors, and future prosperity expectations. Based on an fsQCA of changes in life circumstances of 166 farm households in rural Kenya, we explore how different combinations of conversion factors enable distinct forms of entrepreneuring in the pursuit of prosperity. Results show that strong entrepreneurship-enabled future prosperity expectations result from three combinations of enabling conversion factors shaping up three varieties of entrepreneurial endeavors: family-frugal, individual-market, and family-inwards, which show a much more diverse and counterintuitive reality. Our research contributes to literature by revealing and theorizing on a split picture portraying the many ways in which farmers, acting as everyday entrepreneurs, exploit real opportunities in seemingly identical impoverished communities. It also reveals a central disconnect between entrepreneurship, life-satisfaction and financial improvements when assessed against expectations of future prosperity. In doing so, this paper responds to calls for a better understanding of the processes whereby entrepreneurship can distinctively improve current and future life circumstances, and the many ways in which this may happen.