We’re excited to introduce you to the always interesting and insightful Gabrielle Wyatt. We hope you’ll enjoy our conversation with Gabrielle below.
Gabrielle, thanks for taking the time to share your stories with us today What’s the backstory behind how you came up with the idea for your business?
At a young age, I led structural change in New York City Public Schools and Newark Public Schools—some of the largest school districts in this country. I was focused on ensuring that the brilliance of every Black child was nurtured and actualized so they could have multi-generational opportunity.
I was eager, excited and focused, but I was growing increasingly burned out. As a young leader, I hadn’t yet understood nor explored the ways to personally sustain myself, and my well-being. I thought that 80-90 hour weeks were the norm for public servants, and too often, I would deprioritize things as seemingly simple like an annual health exam. Over time, I began to see the very real wear on my body and my relationships.
When I started working in philanthropy, I began to notice that I was not alone in this experience as a Black woman leading structural change. I saw up, close and personal, the complexity of burn out. Burn out was not just driven by long hours, but by the often toxic nature of fundraising, from receiving fewer dollars and the mental gymnastics of hearing a lot of no’s, to not having access to spaces and places to truly rest, heal and imagine what could be possible.
In one of my roles as Partner at The City Fund, an organization that provides grant money to create innovative school systems, I designed and piloted a fellowship program for Black and Latinx education and advocacy executives with a focus on building a bench of leadership, and sustaining it. This pilot unfolded against the backdrop of looming COVID-19 shutdowns and eventually the complete devastation we would see in Black and Latinx communities from the virus. I began to hear more anecdotally and see in the data that the pandemic was a threshold moment for Black women leaders and their burnout, with many of us leaving our fields. It was then that I heard the very clear alarm bells warning about the real challenge to the sustainability of structural change: we do not invest in space, places, and capital to sustain Black women leaders. Having led structural change in the very same systems as my grantees in the past, it became clear that we would not be able to create real, sustainable change if we don’t figure out how to sustain Black women. And that one day, we will wake up, and see that these incredible leaders who we provided grant money to, who did an incredible job serving our children, are not going to be there. We need to think about how we are sustaining them by honoring their brilliance and humanity.
I had a really empowering executive coach, who encouraged me to dream about what this could look like. I also worked with a supportive organization, and they seed-funded me to go business plan, to learn, to listen, to do exactly what our capital does for Highland Leaders today. The rest is history.
As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your back background and context?
America is at an inflection point, where what we do now, and in the next few years, matters. As a country, we continue to see how racial gerrymandering has deprived Black people of political power. As a country, we continue to see that Black women are being paid 61 cents for every dollar made by white men. As a country, we continue to see Black communities being disproportionately impacted by COVID-19, experiencing worse health outcomes and with less financial security. But these are more than headlines—it’s a clear proof point that 400 years of slavery have continued to create a hierarchy on the lines of race, gender, age, and sexuality, and it is eroding opportunity and prosperity for Black women and their communities.
Despite the challenges and barriers for Black women across America, our stories are one of power. Over decades and generations, we have demonstrated tremendous political power. Economic power. Education. Ambition. Our contributions to culture—in academia, literature, social change, music, fashion, feminism, and so much more—are undeniable. We carry a legacy, not just for themselves, but for their communities to survive, thrive, and always rise.
As our country hopes to look forward, to build a better America that is truly embracing of each of our unique experiences, where there’s a place of belonging and dignity for all of us, it is critical that we invest in the vision that we long for by listening to and centering Black women’s needs, concerns and dreams.
That’s why The Highland Project exists. Launched in 2020, The Highland Project is a coalition of Black women leaders who are designing and leading solutions that create multi—generational wealth and change for Black communities. We invest in the imagination of Black women leaders—because we believe an investment in their humanity and their vision can unlock infinite possibilities.
We provide leaders with $100,000 of direct, unrestricted capital that leaders can use toward scaling the solutions they are driving for Black communities. We also provide community care, and space for them to come together and rest and dream and unlock infinite possibilities. Within an 18 month experience, we curate gatherings anchored around this. To date, we’ve cultivated a circle of 30 Highland Leaders—representing a $3M commitment in unrestricted capital to invest in their legacies.
At The Highland Project, we know that when Black women are together in community, we are the most powerful force in the universe. It’s time to shift the dialogue from one that focuses on Black women’s struggle to one that centers our strength, love and humanity.
Have you ever had to pivot?
After two senior roles in public education, I decided to step into the funding world as I saw the role of philanthropy in seeding local innovations. Specifically, that local and national philanthropy were large actors with good intentions to dramatically change the life trajectory of students furthest from opportunity. But at the same time, often the decision-making tables and grantees did not represent the community. I deeply believe that proximity, that truly centering and co—powering with those closest to the challenges, will change the trajectory and sustainability of how we solve our greatest barriers to opportunity. While I watched the power of philanthropy move through in impactful ways, it became clear that they were not sustainable. And I realized that we needed to shift the way resources were being used to address the root causes of the underinvestment in Black communities—an issue that has spanned decades.
And so, for a number of years, I found myself at key national decision-making tables. The pivot was rewarding and hard. I loved figuring out how to move resources to entrepreneurs and quickly seeing their visions become reality. It was hard because I found myself confronting challenges we hear about across the philanthropic sector. Often we were moving on short-term solutions for centuries-long challenges. This was usually against the backdrop of decades of underinvestment in leaders of color on the ground. They often began their audacious visions on shoestring budgets. And while they produced incredible impact, the funding often never caught up. The challenge I began to see was three—fold:
(1) Leaders of color too often launched without abundant capital to begin proving concept
(2) Rarely did leaders of color have access to abundant capital to scale their organizations
(3) Rarely did leaders of color have access to capital to dream—to move away from playing daily defense and offense, and imagine what would be needed generations from now.
For me, I believe philanthropy is well-intentioned and yet, changing its very fundamentals can be like moving a government bureaucracy. In the words of Cheryl Dorsey, Jeff Bradach, and Peter Kim, “racial inequity is built into philanthropic norms” — from how a grantee pipeline is sourced, to how “risk” is assessed, to how success is determined and more. Despite the calls and commitments for racial equity in 2020, we continue to see the challenges in moving philanthropy at a pace that mirrors the urgent need for racial justice. We’ve seen little progress in the not only consistent and abundant funding flows to Black—led organizations and solutions, but also limited shifts to trust-based giving.
As I think about this pivot years ago, I see it as a key piece of my own legacy building journey. I am grateful and proud of the seats I held in national philanthropy. I can see the impact of that time and how those experiences shaped what would ultimately become The Highland Project—an ecosystem that is for us, by us, and funds the dreams and sustainability of Black women.
We’d love to hear a story of resilience from your journey.
I think it goes without saying that launching a non-profit organization focused on trusting the brilliance and future impact of Black women is incredibly rewarding. It also tests your resilience daily. From constantly pitching your vision often to a room that does not look like you, to hearing a lot of no’s, to the pressures of holding up a vision of abundance over scarcity like we are taught.
Perhaps the greatest gift I was given in this journey was having the time, space, and stillness of the rolling pandemic shutdowns. During a time of tremendous loss and uncertainty, I found my legacy vision again. I’m not sure I would have found it as quickly if I wasn’t forced to slow down. It helped me to deeply question how I thought change was seeded, built, and sustained. It helped me to question what would be needed to not only recover from the pandemic, but continue to be in pursuit of racial justice and liberation.
The gift of the shutdowns was intention. I began to identify what my tools and practices would be to get me through the times that would test my resilience. From intentionally building my cabinet of Gabby cheerleaders who would also hold me accountable and intentionally exploring my relationship to sustainability and rest in order to set a new path that was not defined by burnout.
Contact Info:
- Website: www.thehighlandproject.org
- Instagram: http://instagram.com/leadhighland/
- Linkedin: https://www.linkedin.com/in/gabrielle-wyatt-50612a8/
- Twitter: https://twitter.com/LeadHighland
Image Credits
Justin Ross