Why some individuals choose to become business owners is not entirely clear. Some scholars have argued that a more holistic approach that includes examining personality traits, social context, and developmental periods in the lifespan should provide a deeper understanding of these choices. Tracing the relationship between adolescents' entrepreneurship orientation and their educational aspirations, school engagement, and conformity when in secondary school, can contribute new insights into the pathways of business ownership. Results from a series of structural equation models, with a constructed latent variable of school attachment, using a national longitudinal study of over 9,000 U.S. adolescents and their subsequent career choices in their late 20s, reveal a pattern of entrepreneurial development. Business owners, even as adolescents, showed a strong entrepreneurship orientation but lacked an attachment to school. This career trajectory, however, differed for females and males.