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Wage employees enter self-employment either directly or in a staged manner and may subsequently undertake multiple stints at self-employment. Extant research on the relationship between entry modes and the persistence and outcomes of self-employment is inconclusive. This study investigates the relationship between wage employees’ initial mode of entry into self-employment and the duration of the subsequent first two stints of self-employment.

This study used a matched longitudinal sample of 9,550 employees who became majority owners of incorporated firms from 2005 to 2016.

The findings demonstrate that the initial mode of entry into self-employment matters for the first two stints at self-employment. Staged entry into self-employment was associated with a shorter first stint and became insignificant for the second stint. Staged entry into self-employment was positively related to the odds of becoming self-employed for the second time in the same firm.

Using a comprehensive and reliable dataset, the paper shifts focus from the aggregated onward journey of novice entrepreneurs (survival as the outcome) to the duration of their self-employment stints. By doing so, the paper offers insights into the process of becoming self-employed and the patterns associated with success/failure in entrepreneurship associated with self-employment duration.

All entrepreneurs interact simultaneously with multiple entrepreneurial contexts throughout their entrepreneurial journey. This conceptual paper has two central aims: (1) it synthesises the current literature on gender and entrepreneurship, and (2) it increases our understanding of how gender norms, contextual embeddedness and (in)equality mechanisms interact within contexts. Illustrative contexts that are discussed include entrepreneurship education, business networks and finance.

This conceptual paper draws upon extant literature to develop its proposed conceptual framework. It provides suggestions for systemic policy interventions as well as pointing to promising paths for future research.

A literature-generated conceptual framework is developed to explain and address the systemic barriers faced by opportunity-driven women as they engage in entrepreneurial contexts. This conceptual framework visualises the interplay between gender norms, contextual embeddedness and inequality mechanisms to explain systemic disparities. An extra dimension is integrated in the framework to account for the power of agency within women and with others, whereby agency, either individually or collectively, may disrupt and subvert the current interplay with inequality mechanisms.

This work advances understanding of the underrepresentation of women entrepreneurs. The paper offers a conceptual framework that provides policymakers with a useful tool to understand how to intervene and increase contextual embeddedness for all entrepreneurs. Additionally, this paper suggests moving beyond “fixing” women entrepreneurs and points towards disrupting systemic disparities to accomplish this contextual embeddedness for all entrepreneurs. By doing so, this research adds to academic knowledge on the construction and reconstruction of gender in the field of entrepreneurship.