While gender equity appears to be moving at glacial speed in contemporary societal debate, many argue advancement toward equitable outdoor leadership has been stymied. Hearing and responding to lived experiences and stories can be an impetus for transformational change. The experiences of all genders, as well as nonbinary and agender people, attest to the need for a major shift within the outdoor professions. Together, as a unified voice, we explore our diverse perspectives and professional journeys as reflexive practitioners. By sharing our biographical sketches with a particular focus on gender influences, through our philosophical approach we intend to highlight efforts underway to redress gender inequities and promote institutional and cultural adjustments. We detail attempts to raise awareness, gather resources, and promote effective entry points into the conversation. We describe our perceptions of the gendered landscape and pinpoint areas of future focus to elevate understandings of inclusive outdoor leadership. Radical and unilateral progress is needed, and we offer tangible and inclusive pathways to move this critical agenda forward within various spheres of influence.