#117: Why Nonprofit Leaders Need Peer Support and Community Now More Than Ever

Natalia Kay-O’Brien returns for her third appearance on Take the Leap to talk about what it really looks like to keep building community while everything feels like it’s on fire (politically, socially, financially… pick a lane). She shares how a tough year, including losing a major retainer, pushed her into deeper R&D and ultimately into creating new, more intentional convenings for nonprofit and social services professionals.This episode explores the shift from “doing it all alone” to building collaborative, relationship-centered spaces where people can be honest, supported, and strategic, without being talked at by the usual conference circuit.If you work in nonprofits, social services, or any community-centered work and you’ve been feeling isolated, overwhelmed, or just plain tired, this will feel like a deep exhale.Note: This episode ends abruptly due to technical issues, but the conversation we did capture is packed with timely insight for the Portland nonprofit space.Key Takeaways: 2025 forced a reset. Losing stable income pushed Natalia to rethink what she wanted her work (and business) to actually be about.Convening is the strategy. Gather (her quarterly happy hour) became proof that people are hungry for connection, and inspired her to build more structured experiences.People need spaces to downshift. Natalia emphasizes regulation, slowing down, and resisting the “urgency treadmill” that burns out helpers first.The Nonprofit Confluence challenges the conference model. Less “expert panels,” more peer wisdom, relationship mapping, asset mapping, and shared visioning.Visioning is survival. Turning away from fear-based consumption and toward imagining what we want to build is part of staying in the work long-term.Tune in to our previous conversations with Natalia Kay-O’Brien, episodes #10 and #82 on Apple Podcasts, Spotify, and YouTube. Guest & Host Information:Guest, Natalia Kay-O'Brien, Owner of Affinity ProjectsCo-Host, Ashlan Glazier-Anderson, Owner of AshbeanPDX MarketingCo-Host, Victoria (Tory) Proppe, Owner of Imagine Marketing StrategiesConnect with Natalia:Visit the Affinity Projects website: https://www.affinityprojects.net Find Natalia on LinkedIn: https://www.linkedin.com/in/nkayobrien For Portland-area folx, join Gather, a happy hour for social good: https://www.affinityprojects.net/gather And Portland-area nonprofits, check out the Nonprofit Confluence, A Solidarity Summit: https://nonprofitconfluence.org The Course: The Take the Leap course contains everything you need to know to successfully launch your business now. Sign up today to join the course and get support from Ashlan & Tory who will guide you through your journey as a new entrepreneur.Sign up here: https://www.taketheleap-today.com/the-course Like our content? Be sure to subscribe and review! Want to keep in touch? Find us on:YoutubeInstagram