This year both the Tamarack Institute (Canada) and Inspiring Communities (Aotearoa New Zealand) achieve significant milestones. They are celebrating 15 and 10 years respectively in their efforts to empower, grow, support, connect and learn from diverse community-led change efforts. Having mutually benefitted from peer-learning exchanges over the years, it felt timely to compare and contrast experiences and observations from the collective 25 years of wisdom gathering. This paper shares that learning.