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This chapter is a reflective evaluation of the preexisting and emerging issues and challenges which mediate contemporary efforts to sustain gender justice in the Caribbean. I use the perspectives of undergraduate feminist theory students and online feminist activists to establish how contemporary Caribbean feminist advocacy is situated. I also evaluate this situatedness by considering the salience of perspectives and sentiments inherited from a legacy of collective consciousness raising through developed Caribbean feminist theorizing and vibrant women’s movements in the region. I assert that student responses reflect an awareness of this legacy with an understanding of self as inheriting a secure agency as a collective, particularly as a collective group of women, but at the same time expressing a preoccupation with the individualistic, particularly in terms of concerns over bodily autonomy. This suggests a turn from their legacy. In addition, online feminist activists lament that change is not as evident as needed; that they still live limits, are still subject to gendered structures of power, and that struggles over legitimacy and for freedom from gender-based violence continue to undermine the attainment of gender justice. Their sentiments suggest that the “there” has been engaged but by no means arrived at as a fixed end point; while some agency can be accessed, gender justice in the region continues to be a journey that is complex and requires response to an ever changing social, political and economic landscapes.

The current changes and relevance of female entrepreneurship at the national and international level for economic growth, social impact and environmental degradation highlight the need for more analysis of female entrepreneurial typologies and value creations.

This chapter aims to contribute to the field of female entrepreneurship literature. It provides theoretical evidence about the main internal (personal characteristic and motivation, network) and external (women migration, crises, digitalization) drivers that trigger women entrepreneurs to undertake entrepreneurial actions in national and international contexts. Besides, this chapter conceptualizes a new untapped context of multiple value-creating entrepreneurial systems in the female entrepreneurship literature by uncovering a blended form of value creation encompassing several social, economic and environmental levels.