In this episode of The Impostor Syndrome Files, we explore how lived experiences shape leadership and influence the way impostor syndrome shows up at work. My guest this week is Natanja Craig-Oquendo, Executive Director of the Boston Women’s Fund. Natanja shares her journey from a childhood grounded in community organizing and allyship to leading mission-driven work focused on social, gender and economic justice. She reflects on how early messages about identity and belonging shaped her sense of what was possible and how those messages continue to influence her inner dialogue today.

In our conversation, we talk about the power of representation, the impact of environment on confidence and how focusing on service can shift attention away from self-doubt. Natanja also introduces the idea of “imprint vs. impact,” reminding us that while impact builds over time, imprint happens in every interaction through how we show up and support others. We also discuss what it takes to lead with honesty and humanity, why creating space for real conversations matters and how to move away from compartmentalization toward more authentic leadership.

About My Guest
Natanja N. Craig-Oquendo is CEO of Boston Women’s Fund, where she is redesigning philanthropy to follow community leadership — not override it. Guided by the principle “do nothing about us without us,” she has spent more than 20 years shifting power toward the communities most impacted by inequity.

Since joining the Fund in 2020, she has tripled grantmaking, expanded partnerships from 6 organizations to 22, grown the operating budget from $300,000 to $2.2 million, and increased the endowment from $2.1 million to $3.5 million. She advanced multi-year grants of up to five years, pioneered a “Request for Conversation” model to replace traditional RFPs with trust-based engagement, and launched the Seed Funding Grant to expand access to capital for Black leaders and grassroots innovators.

She is equally proud of building an organizational culture that supports the full human — where caregiving is not penalized, boundaries are respected, lived experience informs decision-making, and sustainability replaces burnout as the measure of commitment. In 2025, she co-led Carrying the Weight, Leading the Change, a research report developed with UMass Boston, and founded Horizon Collective, a leadership initiative for women and gender-expansive leaders of color.

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Website: www.bostonwomensfund.org

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