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, we’re thrilled to have you on our platform and we think there is so much folks can learn from you and your story. Something that matters deeply to us is living a life and leading a career filled with purpose and so let’s start by chatting about how you found your purpose.
Ooo, I love this question! It’s at the heart of The Highland Project, the organization I founded where we holistically invest in the legacies of Black women. For us, a legacy is a vision just beyond your reach for how you want your life today to spark multi-generational change seven generations from now. Moving with your legacy or stepping into your purpose is the result of a set of intentional actions, specifically, how you make choices and trade-offs with how and where you spend your time and money personally and professionally.
Right now, I would say I am moving in alignment with my legacy or my purpose to create deep, joyful, healing and sustainable investments in the brilliance of Black communities. But it took a lot of reflection, tough love, healing and shedding to get there, much less be able to articulate that sentence.
I come from a family lineage of public service and investment in actualizing the brilliance of youth. My parents met teaching back home and went on to have three girls, two of which would go on to become teachers. I would catch the education-bug, but it took the form of public policy and board service. I began my journey to articulate my legacy vision as a Board of Education member in Baltimore County. It was there where I began to learn the power of my voice as a biracial Black woman in a room that did not imagine me to be in it, and in an education system that was not imagined to serve me. I did not know it at the time, but the seed of structural change—moving systems, policy, resource flows, and practices to move in alignment with a vision of true equity—was planted and nourished during that time. The experience would lead me to some of the largest school districts in this country and roles in national philanthropy to lead structural change. I was focused on ensuring that the brilliance of every Black child was nurtured and actualized so they could have multi-generational opportunity. My focus was almost impenetrable—and everyone felt that, including me. But prioritization of work over relationships, of work over self-care would eventually come to a tipping point.
That tipping point was 2019. I was burnt out, jaded, and unwell. And when I looked around, many of my peers, mentors and sheroes were at similar and worse tipping points. This all was against the backdrop of cities beginning to shift into shutdowns. For the first time since I could remember, like so many people that year and in the years that would follow, I was forced to be still. For such a devastating time, the stillness was a gift for me to get back on my legacy path.
My recipe for doing that became hiring a coach, Shawna Wells—a legacy mastermind; getting out of my comfort zone to explore my own well-being so that I, too, could thrive and imagine what thriving Black communities could really look like; and creating circles of trusted friends and mentors to vision with. The vision I saw was one of groups of Black women across sectors and generations experiencing joy and healing. I saw them having access to abundant resources—time, space, and capital—to imagine and build the communities where they could truly thrive.
The process of visioning helped me to see where my life was leaving a trail of breadcrumbs about the legacy I aspired to leave behind. They were a trail of examples of creating investments in actualizing Black brilliance. But it also revealed to me the trail I was on would not be sustainable if I also wasn’t sustained.
And so my real legacy journey began, where I focused on what I needed to be sustained as a Black woman, as well creating spaces where present and future generations of Black women could ask that exact same question with resources and community care supporting them.
Thanks, so before we move on maybe you can share a bit more about yourself?
I am the founder and CEO of The Highland Project, an organization that invests in the humanity, impact, joy and sustainability of Black women leaders.
If you had to pick three qualities that are most important to develop, which three would you say matter most?
As I think about my journey to find my legacy vision, I think about the lessons in belonging and co-powering that I learned from the late Dr. Joe A. Hairston, former Superintendent of the Baltimore County Board of Education. We served on the Board together when I was 17 years old, and I will never forget how he made me feel valued and seen in and outside of the boardroom. The most memorable experience I had with him was spending a year traveling to every high school in the county. Sometimes announced, sometimes unannounced. We wanted to speak with students who typically did not have the same access to Board members and the Superintendent. Our goal was simple: to understand what was and was not working in the school building as they pursued their dreams. I will never forget one of the first meetings when he asked to speak with the Principal of the school afterwards about what we heard. I remember shrinking into my role of “student” and insisting I’d wait in the lobby of the main office. But Doc nearly dragged me into the room, naming: “you deserve to be here as much as me.” It was a lesson in co-powering and ceding power that I will never forget.
Another piece of knowledge that impacted my journey was learning with my former coach turned sister-friend Shawna Wells and rest coach turned Chief Daydreaming Officer at The Highland Project Octavia Raheem the necessity of discipline in walking in alignment with your purpose or legacy. Discipline is a set of decisions about the actions and mindsets you will allow to fill your calendar and bank account. It requires a deep understanding that you cannot keep adding to the to-do list. That for everything you add, you must take at least one thing off. You must audit your calendar and spending, personal and organizational, asking “does this reflect back to me my vision?”
Awesome, really appreciate you opening up with us today and before we close maybe you can share a book recommendation with us. Has there been a book that’s been impactful in your growth and development?
Octavia Raheem’s first book Gather. It got me through the first shutdown in NYC and became an anchor framework for The Highland Project. If I were to write the Cliff Notes of Gather, here’s what it would say:
– Black women and communities have always been powerful and we’ve always had the answers. Right now, we’re on a generational assignment to remember that and excavate our generational brilliance.
– The path to remembering is not submitting to grind culture. It is about waking up to the necessity and power of rest and stillness.
– Our legacies—the ones passed on to us and the ones we are creating—carry trauma. We must step into healing and shedding the traumas that are not ours to own.
– Rest is our superpower. It opens a portal to seeing a future of freedom and joy for Black women and communities.
Contact Info:
- Website: www.thehighlandproject.org
- Instagram: @leadhighland
