This study explores whether longitudinal individual and rural-urban conditions during adolescence (13-17 years old) influence an individual’s decision to pursue self-employment as an early-career option (ages 21-31), with a comparative lens at a time of an economic recession. Self-employment is typically studied as an isolated event rather than as part of an individual’s career continuum, and it generally lacks a comparative examination of rural-urban conditions. We use a composite entrepreneurship-careers lens to advance our current knowledge of rural-urban conditions and temporal patterns affecting entrepreneurial activity. We use a national longitudinal survey which tracked individuals from adolescence to adulthood, and which comprises a nationally representative random sample of 9,022 individuals who were between 13 and 17 years old when they were first interviewed in 1997. They were interviewed every year since. Our comparative results indicate that rural-urban conditions, along with individual factors such as gender and job satisfaction, influence the decision to become self-employed as an early-career path, with varying effects at a time of an economic recession.