What the Prebys Leadership Awards Teach Us About Leadership

As someone who has spent years serving, advocating for, and walking alongside leaders at every stage of their journey, from emerging changemakers to deeply tenured community visionaries and stewards, there is something profoundly affirming about witnessing leadership itself be celebrated. Not simply the title or position, but the action of showing up for community again, and again, and again. 

Visibility is powerful – and I am not referring to the visibility built for LinkedIn captions or gala moments, but the kind that says: we see what it takes to care this deeply about community. We see your work, your sacrifice, and your commitment. Most importantly, we see you and appreciate you. 

That, perhaps more than anything, continues to sit at the heart of what we are learning through the Prebys Leadership Awards. 

The program was designed to honor visionary leaders across San Diego County whose work advances health and well-being, medical research, youth success, and arts and culture. Each year, five leaders receive a $100,000 unrestricted award to accelerate their work and celebrate their impact publicly. Simple (enough) on paper. But now, three cohorts in, it’s become increasingly clear that the true power of the awards extends well beyond the monetary award. 

Or, perhaps more accurately: the monetary award is only one chapter of the story. 

Since launching in 2023, the awards have helped surface a deeper understanding around the importance of supporting leadership itself as an act worthy of investment — not simply the outcomes, organizations, or initiatives attached to that leadership. In philanthropy, we often talk about concepts like scaling, impact measurement, innovation, etc. Historically less common, though becoming more familiar today, we are asking: what does it mean to sustain the human beings carrying the emotional, intellectual, and spiritual weight of community transformation? 

Imagine, if you will, an Avengers-style crossover scene, but instead of saving the multiverse, everyone was sharing reflections from their own universes: wins, losses, burnout, transitions, community trust, family, and the state of the world. (The consensus: ​“There’s a lot going on.”) 

There was something profound happening across these universes. 

The conversation illuminated several learnings that continue to shape how we are thinking about the Awards, and leadership more broadly. 

First, the importance of the program serving as a nexus point for connectivity, support, and imagination.

Again and again, awardees reflected back to us on the value of being intentionally convened — not merely celebrated in isolation, but brought into relationship with one another. As someone who occasionally forgets the quiet power of simply gathering people with care and purpose, this felt like an important reminder for me personally. 

Convening creates familiarity. Familiarity can grow into trust. Trust often becomes opportunity for collaboration. And collaboration, at its best, strengthens the connective tissue of our community. 

The awards affirmed that foundations have the potential to leverage resources far beyond grantmaking alone. Sometimes the most catalytic thing philanthropy can do is create the conditions for leaders to encounter one another honestly and without performance, urgency, or the transactional choreography that too often shapes our sector. 

Second, there was a powerful reflection around storytelling and visibility. 

Too often, communications in philanthropy can unintentionally drift toward institutional self-congratulation or carefully polished narratives that feel oddly detached from the people at the center of the work (my hope is that this is not one of those occasions). What emerged from the cohorts, however, was a reminder that storytelling is not merely a marketing exercise; it is an opportunity to connect aligned communities, stakeholders, and future collaborators to the work itself. 

Stories create proximity. Proximity can grow into empathy. Empathy has the potential to be an engine of action. 

Awardees spoke about the significance of being publicly recognized by the foundation and connected to a legacy rooted deeply in San Diego’s civic and philanthropic history. That kind of recognition can amplify credibility. It can open doors. It can introduce leaders and organizations to broader audiences who may have never encountered their work otherwise. 

The power of communications, when used thoughtfully, can dignify leadership rather than commodify it. I think that distinction matters. 

And finally, and perhaps most movingly, the cohorts reflected on the humanity embedded within an unrestricted individual award of this size — because leadership, especially community-centered leadership, can often extract from people in ways we are rarely aware of and acknowledge openly. 

There is emotional labor. Spiritual labor. Familial labor. The quiet accumulation of sacrifice that often accompanies a life committed to service in the nonprofit sector. Leaders pour into communities, organizations, movements, and young people while simultaneously navigating the ordinary complexities of being human themselves. 

Rent is still due. Parents age. Children need support. Rest sometimes becomes a luxury. Therapy copays remain offensively expensive. And let’s be honest, most people do not go into nonprofit work with the promise of wealth and excess. 

So, when awardees spoke about what the monetary component meant, they did not speak about expanding a program or launching new initiatives — though certainly those things matter. They talked about breathing room. About caring for family. About finally taking time to pause and recenter. If even momentarily, stability and groundedness can sustain a leader and their work for longevity… or, long(er)-evity. 

And honestly, that matters too, right? Perhaps more than philanthropy makes room for in funding strategies. 

Awards like these do not simply impact individuals, they ripple outward into families, support systems, organizations, and communities. They create moments where leaders are invited to remember their own humanity while continuing to steward the humanity of others. 

That feels increasingly important in this moment. The future of our communities may depend less on finding ​“perfect” solutions and more on whether we can sustain the people courageous enough to keep showing up in them. 

The Prebys Leadership Awards continue to teach us that leadership is not merely a demonstration of benevolence to celebrate, it is a human practice to nurture and support. 

And perhaps that’s the real award.