Side-hustling – the engagement in diverse income-earningactivities – has become a common phenomenon among Kenyan educated youth who are increasingly faced with formal employment uncertainties. In this article, I examine how aspirations and expectations of educated youth are formed within their opportunity space, involving their assessment of what is possible within their geographical, socioeconomic and political contexts, and given their own qualities and characteristics. Through the life stories of six educated young farmers interviewed in 2014, I show how side-hustling offered them an alternative livelihood strategy; a means for self-improvement; and a reconfiguration of their imagined futures. The article suggests moving beyond our deductive statistical analyses of who is employed and who is not; and instead utilising a youth livelihood framework which helps to understand how young people make meaning of themselves and opportunities around them in extreme socioeconomic conditions.