Recap: Embracing Risk to Lead With Courage - PNY’s 2026 Annual Learning Meeting
On Tuesday, March 31, the Philanthropy New York community came together for our Annual Learning Meeting, Embracing Risk to Lead With Courage. The half-day convening provided PNY members with opportunities to embrace courage through crisis and connect with peers.
Following the fireside chat, members joined one of three breakout sessions based on areas of interest or organizational roles. We’ve put together a breakdown of each session and what some of our members learned and are bringing back to their own organizations.
The afternoon began with Courage Through Crisis, a fireside chat between Deepak Bhargava, President of the Freedom Together Foundation, and Kathryn O’Neal Dunham , President and CEO of PNY. Deepak offered a candid assessment of the current democratic crisis, examined what courage in practice truly looks like, and made the urgent case for institutions to stand together in solidarity with other pillars of society to protect our democracy.
PNY Members, watch the recording of our PhilTalk with Deepak Bhargava here.
Session A: A Self to Systems Practice
In A Self to Systems Practice, Bianca Anderson, CEO, and Monica Biswas, Director, of ProInspire introduced ProInspire’s Creative Courage framework to an audience of programming staff and rising leaders in philanthropy. The framework is designed as a lens for understanding and practicing risk-taking grounded in vision, equity, and sphere of influence, rather than in scarcity or fear.
Session participants were guided through a four-part arc:
- Self: examining how personal history and soci2w22alization shape risk responses
- Role: mapping where participants have direct control and influence
- System: applying Creative Courage to the sector-wide crises philanthropy is navigating right now
- Commitment: leaving with one concrete, vision-aligned action and an accountability partner
Identity, socialization, and lived experience shape individual and organizational views of risk and decision-making. Through guided reflection, small group dialogue, and practical exercises, Bianca and Monica guided members in identifying where they have influence within their role and provided space for them to practice taking courageous, values-aligned action within their sphere of control.
After the session we spoke with PNY member Vanessa Rivera of the Solon E. Summerfield Foundation about her experience and takeaways from the session.
Session B: Scenario-Planning For Polycrisis
Alana Tornello, Director of Resilience at the Human Services Council of New York, helped move PNY members past uncertainty and into decision and action. As the impact of federal actions merge with everyday emergencies and inequities, services providers are in a polycrisis.
This session introduced operational and legal staff, CEOs, and members focused on organizational strategy to key components of a resilience strategy through a variety of plausible scenarios to help discern leadership stances, build response structures, assess risk, and more. By establishing practical frameworks that help organizations stay prepared rather than reactive, the philanthropic sector can move past uncertainty and into decision and action. We caught up with Sabrina Hargrave of Brooklyn Org after the session.
Session C: Strategy in Solidarity
Solidarity is more than a statement — it is a strategic practice. At PNY, we have worked to build solidarity into our strategic framework and provide opportunities for members to do the same. In this session, Adaku Utah, Director of Movement Building Programs at Building Movement Project, introduced PNY members to a framework that further supports solidarity as a strategic practice. Solidarity Stances, developed by Building Movement Project and Solidarity Is, is designed to help organizations build deeper, more aligned forms of solidarity, while honoring their unique context and constraints.
Using this framework, Adaku guided senior leaders through reflections and small-group dialogue to assess their organization’s capacity and consider the most strategic ways to respond to solidarity requests, public pressure, and internal decision-making in complex political conditions. After the session, we spoke with Tiffany Smith from Ideas in Philanthropy.
Our half-day of learning, connection, and embracing risk to lead with courage was brought to a close with a powerful performance by the Resistance Revival Chorus. Together, in song, the PNY community reconnected and realigned, breathing joy and song into resistance.
As always, we are grateful to each and every one of our members for contributing to the resilience of our community and the impact of our work. If you attended the Annual Learning Meeting, we hope you left feeling inspired, renewed, and courageous in your work to continue advancing meaningful social change. If you weren’t able to attend or are looking for ways to engage with the PNY community, check out our upcoming programs here.