As the cultural and political climate continues to ebb and flow, organizations in the outdoor sector face crucial decisions about engaging in Diversity, Equity, and Inclusion (DEI) work. This session explores the risks of both engaging in and avoiding DEI initiatives under the evolving political landscape, particularly during the Trump administration era. Attendees will learn how organizations can navigate challenges such as stakeholder backlash, reputational risk, and policy changes, while also recognizing the opportunities that DEI work brings for fostering inclusivity, innovation, and resilience. Through interactive discussions and activities, participants will assess their organization’s current DEI position, identify strategies for mitigating risks, and develop actionable steps to enhance inclusivity while aligning with organizational values. This session offers a supportive space to examine how wilderness organizations can remain adaptive, forward-thinking, and mission-driven, even in uncertain times. Join us for a thought-provoking conversation on balancing challenges and opportunities to create a stronger, more equitable future in the outdoors.