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“Hope is the thing with feathers-
That perches in the soul-
And sings the tune without the words-
And never stops- at all-“
— Emily Dickinson
Dear Amy,
Courageous action begins with hope along with the belief in and vision for what is possible. The belief that you can create something, that what you build will matter, that the world can be other than it is. You do not take a risk without first believing the risk is worth taking. Hope is the foundation. Courage is what you build on it. |
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| Creating My Calling
When I founded Essential Leadership in 2018, my calling had already been taking shape for decades through thirty years of Philadelphia civic life, through leading foundations and nonprofits, through training in family systems, positive psychology, and multigenerational philanthropy. What I brought together was professional coaching and deep philanthropic expertise, the inner work and the outer work, braided together in a way I had not yet seen offered to families navigating the complexity of giving across generations. It did not arrive in a single moment of inspiration. It evolved, gathered, and became undeniable. And in 2018, the time came to create it.
What I did not anticipate was how much patience and persistence that belief would require. Building something meaningful is rarely linear. It asks you to stay committed on the days when the path is unclear, to trust the work when the work is quiet, and to keep showing up for the vision even before the vision is fully visible to anyone else. That is the unglamorous middle of creation, and it is where most meaningful things are actually built.
As Essential Leadership was taking shape, I said yes to the opportunity to go deep with one family, to help create something lasting from the inside. My head and heart are in that kind of work, and together we created something meaningful. When that chapter was ready to be carried further forward, I felt the pull to return to the broader practice, to bring everything I had learned and practiced to multiple families, to go as deep and as broadly as my calling was asking me to go.
That return last year to serving multiple families was its own kind of courage. The quieter, steadier courage of recommitting to something that I have always believed in. Of trusting that families needed this kind of coaching and support and that what I had to offer was unique and had only deepened through every chapter that had come before.
Courage, to me, is a practice. It is a choice you make, and then make again. |
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| A Profile in Courage
The courage of creation is not always a solitary act.
On Thursday evening, I was among more than 1,000 people who had gathered to celebrate ten years of Philadelphia Youth Basketball. Four generations of contributors and coach-mentors, young people and community leaders, elected officials and grassroots organizers, people from every walk of Philadelphia life filled the room. The energy was palpable. It had that quality you cannot manufacture: the feeling of something real, something necessary, and something truly profound.
I have watched my husband Kenny and his team build PYB from a concept paper into a 100,000 square foot center that now serves more than 1,250 people a day. I have watched him ask nearly everyone he has ever known, from childhood through law school through decades of civic life, to believe in something that did not yet exist. I have watched him hear “no”, be ignored, and be deferred more times than I can count. And I have watched him push forward anyway, with more clarity and determination each time.
The roots of PYB were firmly planted when his co-founder Eric and others in the basketball and youth development community asked a deceptively simple question: why not basketball? Why, in a city where basketball is iconic, where it crosses every neighborhood, every generation, every cultural and economic boundary, did the sport with the fewest barriers to entry have so little institutional support behind it? Sports like tennis, squash, and rowing had mature organizations, dedicated facilities, structured programming, and the philanthropic investment to sustain it all. Basketball had none of that, despite having far greater cultural pull and far more people of the game who could speak directly to the lives of young people across Philadelphia. Something clicked in the gradual, gathering recognition that this was an idea worth doing, worth exploring, worth staking something on. I remember saying to Kenny, “You cannot not do this”. And do it he did.
The Sixth Man Center that Kenny and his team built was never really about basketball alone. Basketball is the entry point, the culturally resonant, community-rooted vehicle for something far larger: a holistic center for youth development, a trusted space where young people are known, believed in, and connected to something larger than themselves. Today PYB is home to seven partner organizations working side by side and a staff of coach-mentors who pour belief and inspiration into young people every day. A second phase is already taking shape, focused on career credentials, workforce development, and economic mobility for young adults.
Kenny calls the building and development of PYB a trek rather than a journey, and the distinction matters. A journey implies a clear path. A trek is harder to achieve. It requires reckoning honestly with yourself and with those you love about whether you are truly willing to throw yourself in at the deepest level of immersion. And then beginning, with the courage of conviction as your compass.
Ten years later, more than 4,000 contributors so far have invested in what PYB has built. Built of, by, with, and for the Philadelphia community, the center is alive with the people it was built for. What Kenny and his team have created is bigger than any one of them. That is what happens when courageous creation is rooted in community: it grows beyond what any single person could or should hold. |
| Courageous Conversations
Having an honest conversation with your loved ones is one of the most important acts of courage in philanthropy. Often avoided, it can feel like the most daunting place to begin, and may stop efforts before they start. The question I hear most often is simply “Where do we start?”.
We start with why. What motivates us and brings us to this work. What experiences have influenced us and shaped our beliefs. Before a family can create something together, they have to be willing to say what they actually think, what they actually value, what they are actually hoping for. Before a philanthropist can fund boldly, they have to be willing to sit with the discomfort of uncertainty and make the bet anyway. Our willingness to find common ground and hold the tension between different perspectives is the hardest work. And it begins with courage.
When I sit with families, I offer three simple ground rules to begin:
- Share openly. Bring your genuine perspective. This conversation is most useful when everyone is candid about what they think and feel.
- Listen to understand. Make space for each other’s full thought before responding. We are here to understand, not just to be understood.
- Assume good intentions. We each come to this work with care for the family. Let that be the starting point, even when we see things differently.
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“Make no little plans; they have no magic to stir men’s blood and probably themselves will not be realized. Make big plans; aim high in hope and work.”
— Daniel Burnham
The Courage of Conviction
Across the philanthropic landscape, I am witnessing courage take shape in ways that are quiet and extraordinary at the same time.
I am watching philanthropists step into their own power, some for the first time, with a readiness and a joy that has clearly been waiting for the right conditions to emerge.
I am watching families do the harder work first: asking whether they are truly aligned before inviting the next generation to the table, choosing honesty over the appearance of harmony.
Voices are being heard and perspectives welcomed as next-generation family members take a genuine seat at the table, and what opens up when that happens is remarkable.
I am watching families invest in the infrastructure of togetherness itself, creating the vessels that will hold them across time and disagreement before the need is fully visible.
I am watching philanthropists build power in communities, investing in ecosystems and infrastructure alongside programs, doing inner work and outer work simultaneously, showing up boldly in the world.
And some families are asking perhaps the most generous and courageous question of all: whether a loving separation of the family philanthropic vehicle might be the most thoughtful thing they can offer each other, a way to preserve what matters most by giving it room to breathe and grow.
None of it is easy. All of it is worth doing.
And what moves me most is what becomes possible when that individual courage ripples outward, into families, into communities, into the field itself.
“You have to take risks. We will only understand the miracle of life fully when we allow the unexpected to happen.”
-Paulo Coelho
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| The Invitation
Philanthropy means love of humanity. The question before us is whether we have the courage to act on that love, and the imagination to act on it well.
I encourage every person and every family I work with to begin here: imagine the world you want to live in. The one you believe is possible. And then ask yourself what you would like to create through courageous action. What is your thing, the thing that you cannot not do? The feathered thing, that persistent hope in what is possible, is already in you. It has been singing all along, without the words. This is the moment.
Give it words. Get into action. Get to work. |
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Essential Leadership
Essential Leadership works with individuals and families to crystalize their values, magnify their voice, and create their vision for how they will positively impact the world.
What is essential? .
When you identify what is really essential to you, you can eliminate everything else, and make the execution of what really matters as effortless as possible. Knowing what is essential is the disciplined pursuit of less. It allows you to channel your time, energy and effort toward making the highest possible contribution to what really matters.
Why leadership?
When you know your essence, you will identify what speaks to your soul. You rise as a leader in your own sphere of influence, even if you never saw yourself as or aspired to become a “leader” in the traditional sense of the word. You align your passions, your purpose, your life. When you are clear about your vision and strategies for action, you can become a potent force for good. In doing so, you will motivate and inspire others to engage in that vision.
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