Moving from a traditional career to entrepreneurship is a significant shift. It means taking on new responsibilities and dealing with uncertainties. Our research examined what motivates people and the skills they need to make this change. We used career identity theory to understand how people match their motivations, interests, and abilities with their chosen careers. By thematically analyzing 21 in-depth interviews conducted with military veterans and career transition organizations, we find that transition barriers and challenges embedded in career contexts can be overcome by leveraging career capital and social capital through a series of adjustments. The value of career transitions to entrepreneurship was linked to improved well-being, increased autonomy, and satisfaction. We contribute to the entrepreneurship and career literature by proposing an integrative model of work-to-entrepreneurship career pathways, which aids in explaining how occupation contexts shape career aspirations, highlighting the importance of career and social capital and identifying career transition pathways. We propose direction for future research and offer practical implications for employers’ talent management practitioners, individuals considering work-to-entrepreneurship career transitions and interorganizational talent management practices in entrepreneurship ecosystems.