Podcast Summary: Nonprofits Are Messy, Ep 243

Title: What 2025 Taught Us About Real Leadership with Darlene Nipper
Date: December 20, 2025
Host: Joan Garry
Guest: Darlene Nipper (CEO, Rockwood Leadership Institute)

Overview

This candid conversation between Joan Garry and Darlene Nipper explores the seismic shifts in nonprofit leadership witnessed throughout 2025. In a year defined by urgent crises, complex challenges, and high stakes for democracy and community safety, Joan and Darlene reflect on what “real leadership” has looked like, how ordinary people have stepped into new leadership roles, and why investing in leadership development is crucial for the sector’s future.

Key Discussion Points & Insights

1. Redefining Leadership in 2025

• Leadership Goes Beyond the Titled Few:
  • Both guests challenge the traditional notion that leadership is restricted to those in official positions.
  • Darlene emphasizes, “No, actually it is all of us. People are leading in their families, their church and synagogue communities, their community centers… people are showing up where a need has arisen.” (07:56)
• The Myth of the “Nonprofit Industrial Complex”:
  • Joan addresses criticism that nonprofit work isn’t “real work,” citing examples like running a domestic violence shelter or a food pantry as vital and essential labor (00:40).

2. The Rockwood Approach: Leading from the Inside Out

• Darlene explains Rockwood’s philosophy that effective leadership stems from understanding one’s own experiences and emotions and their ripple effects on others.
• "We need a set of skills...that allows us to be skillful in how we show up and collaborate...to get these common goals and visions for the world achieved." (04:09)

3. Leadership in Crisis & Community Resilience

• Emergent Grassroots Leadership:
  • Darlene shares firsthand accounts from Los Angeles during community safety crises (e.g., the Eaton fire, ICE raids).
  • Example: Community members form lookout corners and communication trees, demonstrating rapid, self-organized response when institutions fall short.
  • “Why am I waiting for the government?...I am going to call a couple of people and we're going to hang out on multiple corners where we think we'll have a good vantage point...just report to each other.” (08:49)
• Mutual Aid Evolution:
  • The shift towards mutual aid and spontaneous community organizing—distributing not just food but also information and creating barriers to protect vulnerable people (14:56).

4. Hope Amidst Hardship: Inspiration from 2025

• Community Mobilization Around Threats & Celebrations:
  • Joan and Darlene share stories of their communities rallying to protect one another during ICE activity, particularly at public events like Halloween or Dia de los Muertos (11:53).
• Younger, More Diverse Leaders:
  • Example: Asbury, NJ electing its first Hispanic woman to the Board of Ed, symbolizing new, inclusive leadership (20:44).
• Civic Engagement Surges:
  • Increased election turnout, protests, and collective action are seen as indicators of renewed hope and investment in democracy (18:36).

5. Transforming Organizational & Philanthropic Structures

• From Professionalization Back to Accessible Leadership:
  • Darlene observes a shift from a strictly professionalized nonprofit sector to one with more “easy on-ramps”—low-barrier ways for people to get involved and lead (25:43).
• Leadership Development vs. Professional Development:
  • Both debunk the idea that leadership training is about molding people to fit “white” or traditional professional norms; instead, it’s about broadening access to power, advocacy, and self-determination (27:18).
• Supporting Leaders Beyond Structures:
  • Practical leadership can occur outside formal titles—“It doesn't need to be an ED of an organization...it could be something else in your community that's really just moving the community forward.” (29:53)

6. Challenges & Role of Philanthropy

• Call for Philanthropic Boldness:
  • Both speakers call on philanthropists and foundations to “pivot from what we've always done,” not just supporting immediate needs but also building infrastructure and leadership capacity for the long haul (30:40, 32:35).
• “If you have X million, billion dollars sitting in an endowment somewhere, what are you waiting for?... It is time for foundations to think about...what are you waiting for to give that money out, given everything that's going on?” (33:56)
• The Need to Fund Leadership, Not Just Programs:
  • Joan: “I wish you were the one with the money because you would invest in leaders who are actually going to try to take this work forward and get it over the finish line.” (35:46)
• Let it Hurt a Little:
  • Memorable line from Darlene on grantmaking: “When someone...asks someone to give, it should hurt a little... that's the way it needs to feel for philanthropy.” (46:01)

7. Practical Advice for Leaders and Funders

• For Leaders:
  • “Go deep and hard on what you know...really, this is a time to be almost laser focused.” (41:49)
  • Emphasize both intuition and strategy, stay adaptable and open to pivots—whether that means merging, partnering, or getting smaller before growing again (43:09).
• For Philanthropy:
  • “There’s a role for philanthropy that’s so powerful and so important. It’s called giving money.” (45:13)
  • Fund bravely and substantially, especially in times of crisis—“We need those folks to be brave too.” (47:04)

Notable Quotes & Memorable Moments

• On Leadership's Everyday Face:

  • “No, actually, it is all of us.” — Darlene Nipper (07:56)

• On Community Power:

  • “So stuff like that I think is just profoundly important and really, really helpful to leading.” — Darlene Nipper, referencing grassroots mutual aid during emergencies (10:50)

• On Philanthropic Risk:

  • “If you've been waiting for the rainy day...like, it's a tsunami out there, like, it's the moment.” — Joan Garry (46:27)

• On Hope:

  • “Just the practice of, like, sharing a long view with each other, I think, is an incredibly hopeful, helpful situation.” — Darlene Nipper (17:17)

• On Supporting Leaders:

  • “I imagine you want my brain on what do leaders really need...I think that’s where I should have my brain.” — Darlene Nipper (38:11)

Timestamps for Key Segments

• Redefining Leadership: 00:00–08:49
• Rockwood Leadership Institute Approach: 04:09–06:15
• Community Mutual Aid in Crisis: 07:56–11:53
• Mobilization Against ICE Raids; Halloween/Dia de los Muertos Story: 11:53–14:56
• Hope and New Leaders: 17:17–21:35
• Democracy & Political Engagement: 22:19–23:32
• Role of Philanthropy: 30:35–39:41
• Advice for Leaders and Funders: 41:35–47:10

Tone & Takeaways

The tone is frank yet supportive, with both guests acknowledging the immense pressures facing nonprofit leaders in 2025 but also underscoring the surprisingly vast stores of hope and resilience they’ve witnessed. Real leadership, they agree, is everywhere—often outside the spotlight or unaffected by official titles and structures. Success requires resourcefulness, relationship, community, and above all, brave investment not just by leaders, but by those with the means to empower them.

For those who haven’t heard the episode, this summary captures the essence: 2025 demanded new kinds of deeply personal, community-rooted leadership. The challenges have never been greater, but so too are the opportunities for real, transformative change—if the sector, and its funders, have the courage to act.