The proportion of female-headed households is rising dramatically in sub-Saharan Africa, making women’s income generating activities an increasingly important area of study. As women transition into the role of head-of-household, their traditional activities are augmented with the responsibility of being the breadwinner, and their successes become inextricably linked to the wellbeing of the entire household. In order to create sustainable development programs and policies that support women in this new role, an understanding of women’s current income generating activities must be established. This article seeks to do that through answering two questions. First, how do rural Kenyan women earn a livelihood? And second, what influences a woman’s decision to spend time, sweat, and energy on certain income-generating activities? The findings suggest that there are several underlying factors influencing women’s livelihoods and livelihood-related choices. Some of these factors include prioritizing relationships over occupation, identifying positive factors about their current income generating activities (i.e. comfort, extra food, flexible schedule), and planning for dependents rather than themselves. Moreover, the level of education and number of income generating activities directly impact the total income. These findings allow us to better understand the motivations and influences over the choices of work, as well as initiate a conversation on micro franchise opportunities in developing nations.