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As organizations continue to navigate a changed world amidst the Covid-19 pandemic and the reverberations of the Black Lives Matter movement, many of the issues that affect underrepresented groups in organizations, including women of all different races and ethnicities, have resurfaced with intensity. Missing out on opportunities and being excluded from key decisions, talked over in meetings, and overloaded with caretaking responsibilities, women — and other organizational “outsiders” who are different in some way from the majority group — face obstacle after obstacle in their careers. The authors’ in-depth framework for addressing these issues has the potential to connect individual action to systemic change. Their framework is based on the concept of outsider tolls that members of underrepresented groups have to pay while “insiders” cruise along an open road. Here, they illustrate three specific types of tolls outsiders face in organizations — opportunity, influence, and scrutiny tolls — and reframe them as negotiating opportunities for individuals and as focal points to push for organizational learning and change.