Meet Me at the Highland™

Jul 29 · 1h 15m

“Because of them, I can dream. Because of me, I can make my dreams come true.” —Dr. Dena SimmonsWhat is the emotional soil the next generation will inherit?Dr. Dena Simmons arrives at the Highland with an answer rooted in lineage, liberation, and the courage to stop calling endurance success.Dr. Dena Simmons is an activist, educator, and student of life from the Bronx, New York. She is the founder and executive director of LiberatED, an organization that centers radical love, healing, and justice in education and social and emotional learning to support the mental health of students and educators.In this conversation, Dena calls in the strength of her mother, who came to this country alone at 18 with $25 and created a life for her three daughters. She reflects on her twin sister’s chronic illness, her own health journey, and the years she spent swallowing difficult emotions because being a “good” Black girl meant not causing problems. Those experiences taught her what can happen when children are expected to achieve, endure, and remain strong without anyone asking how they really are.Dena shares how being bullied at Yale and ultimately walking away from the institution forced her to redefine wellness and success. Success could no longer be measured only by accolades, awards, or proximity to prestige. It had to include therapy, family, laughter, emotional honesty, movement, community, and the preservation of her spirit. She names self-preservation as community preservation and explains why the work of caring for ourselves cannot be separated from caring for one another.She also takes us inside the work of LiberatED, where educators and young people are invited to co-create the communities and systems meant to support them. Dena discusses refusing pressure to dilute the organization’s justice-centered language, the difference between neutrality and justice, and why social and emotional learning can become “white supremacy with a hug” when culture, history, identity, and power are removed from the conversation.Together, Gabrielle and Dena explore care as something we must practice rather than perform. They consider what it means to ask people what they need, listen without judgment, and act on what we hear. Dena leaves us with two questions that can reshape the emotional ground beneath our lives: How am I really? What would feel good right now?If Season Two of Meet Me at the Highland™ is an invitation to seed, then Dr. Dena Simmons turns our attention toward the soil we cannot see—the emotional and relational conditions beneath our homes, schools, organizations, and communities. She reminds us that the next generation will inherit more than our ambitions. They will inherit what we normalize, what we make space to feel, and the kind of care we make possible.Connect with Dr. Dena SimmonsWebsite: https://denasimmons.com LiberatED: https://liberatedsel.com Instagram: https://www.instagram.com/denasimmons X: https://x.com/denasimmons LinkedIn: https://www.linkedin.com/in/dena-simmons-9263a918Connect with Meet Me at the Highland™Full episode and companion content: https://open.substack.com/pub/meetmeatthehighland/p/dr-dena-simmons-the-soil-we-cannot?r The Legacy Studio: https://meetmeatthehighland.place Instagram: https://www.instagram.com/meetmeatthehighland YouTube: https://www.youtube.com/@MeetMeatTheHighland (00:00) - Black Women Lead (01:54) - Welcome to Highland (03:43) - Daughter Of Lineage (07:29) - Choosing Joy Daily (09:57) - Redefining Wellness (15:28) - Self Preservation Community (21:54) - Shifting Systems Through Youth (24:50) - LiberatED in Practice (30:20) - Courage Lessons Learned (36:35) - Freedom We Cannot Unsee (40:10) - Including Yourself in Care (41:07) - Daily Practices for Wholeness (43:23) - Kindness Joy and Community (47:39) - Wellness Needs Justice Context (50:42) - Neutrality vs Collective Healing (56:14) - Ecosystem of Care in Schools (01:01:04) - Care Under Real World Threats (01:02:23) - Agency in Healing and Culture (01:08:01) - Seeds to Grow Trust Community Love (01:12:11) - Mad Lib and Closing Blessing

Jul 8 · 1h 17m

What does it take to grow something without burning the soil it grows in? Katara McCarty arrives at the Highland in the second episode of Season 2 with an answer shaped by both her flourishing and her depletion.Katara McCarty is the founder and CEO of Exhale, an award-winning, inclusive well-being app and resource that centers the mental health and well-being of Black women. She also leads Exhale Cares, advancing mental health equity through advocacy, education, and research. Her honors include first place in the NBA Foundation All-Star Pitch and a Webby Award. She is an inaugural Highland Leader and now a coach to many leaders across the Highland.In this conversation, Katara arrives slow and gentle, practicing a pace that does not shove her through the day. She names her lineage: daughter of Betty Waters, who opened her home to a foster baby in 1972, daughter of Mary Waters-Smith, daughter of Nellie Waters, daughter of community and collective care. She places a seed on the altar, a slower, more intentional pace of leadership that does not require depletion to prove impact. She reflects on what the Highland helped her remember about legacy, that it is not only what you leave behind but what you seed forward to flourish seven generations from now. She tells the truth about eighteen years as a pastor and nonprofit leader, holding space for everyone while few held space for her, and about the day in 2016 she landed on her bathroom floor, emptied, asking where to go from here, and the coach who told her to pour back into herself and to grieve. She offers the line that names the whole season: you can grow things, but you do not have to burn the soil. Gabrielle mirrors it back as wholeness, rest integrated with purpose rather than sacrificed to it, and names the difference between care as branding and care as a practice that actually holds us. Katara describes what Exhale really offers, not new care but remembered care, spaces that guide us home to ourselves. She names the vision she will not trade, I see us well, well resourced, well rested. She names what the systems do, deplete and extract, and frames rest and prioritization as refusal. And she closes with the mad lib that holds the arc in two lines: because of them, I can exhale, and because of me, they can exhale.If Season Two of Meet Me at the Highland™ is an invitation to seed, then Katara McCarty tends the question of what the soil requires. Before the planting, the conditions. Before the harvest, the rest. Seed yourself first. Let this episode be a remembering that there is nothing wrong with us, that we are deserving of our own care, and that we can build a different way.Connect with Katara Website: exhale-app.com Exhale Cares: exhalecares.com Instagram: @kataramccarty LinkedIn: linkedin.com/in/kataramccartyConnect with Meet Me at the Highland™ Full episode and companion content: https://meetmeatthehighland.substack.com/p/katara-mccarty-how-to-grow-without The Legacy Studio: https://meetmeatthehighland.place/ Instagram: @meetmeatthehighland YouTube: @MeetMeatTheHighland (00:00) - Intro (02:23) - Arriving Slow and Gentle (03:56) - Lineage Daughter Of (06:38) - Seeding Slower Leadership (09:35) - Legacy Seven Generations (13:33) - Depletion and Turning Point (16:33) - Bathroom Floor Breakthrough (21:55) - Grow Without Burning (27:25) - Relearning Rest from Grandma (30:51) - Rest Fuels Creativity (34:25) - Care as Practice Now (36:11) - Pandemic Spark for Exhale (39:31) - Building Exhale From Frustration (43:08) - Wellness Spaces And Harm (46:05) - Remembered Care And Mirroring (48:41) - What Is Yours To Carry (54:33) - Discernment And Saying No (01:01:42) - Protecting The Seven Generation Vision (01:03:16) - Breath As Daily Resistance (01:07:32) - Support The Movement (01:13:35) - Mad Libs And Gratitude (01:16:03) - Closing Celebration And Farewell

Jun 16 · 1h 12m

What does it mean to plant something for people you may never meet? Season 2 of Meet Me at the Highland™ opens with Brittany Packnett Cunningham, who arrives tracing her lineage and offers the season the faith of a mustard seed. With Gabrielle Wyatt, she explores truth as a daily practice, taking your rightful place, and how to hold love and power in the same hand.Brittany is the founder of Love & Power Works, host of UNDISTRACTED podcast, Chief Strategy Officer of the Children’s Defense Fund, and author of the forthcoming We Are Like Those Who Dream.Full episode and bonus content: meetmeatthehighland.substack.comMore on Brittany: brittanypacknett.com, @MsPackyettiThis is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit meetmeatthehighland.substack.com (00:00) - Episode 1. Brittany Packnett Cunningham: Love, Power, and the Mustard Seed (01:36) - Welcome to the Highland (03:23) - Daughter of Prayer (05:32) - Prayer Crew and Community (07:28) - Seeds Roots and Mustard Faith (14:17) - Showing Up in Fullness (17:32) - Taking Your Rightful Place (28:54) - Learning Self Love (38:17) - Truth Love as Practice (39:18) - Truth Over Survival (40:17) - Truth As Love (44:25) - Building The Truth Muscle (48:42) - Love And Power Together (49:23) - From Emojis To King (55:47) - Dreaming Feels Proximate (57:17) - Why This Book Exists (01:01:59) - Humility In The Writing (01:06:09) - Protecting The Next Generation (01:09:35) - Freedom Mad Lib Farewell

Dec 5 · 4m

A quiet note of gratitude honoring the lineage, wisdom, and healing presence Dr. Gail Parker brought to Season One. A reflection on love as inheritance and love as practice.In this Love Letter from the Highland, Gabrielle reflects on the tenderness and truth Dr. Gail Parker brought to Season One. She honors the lineage that shaped her, the wisdom she carries with grace, and the healing she offers through rest, awareness, and remembrance.This letter is a soft moment of gratitude for the ways Dr. Parker teaches us to return to ourselves. It is a recognition of her legacy, her voice, and the love she practices through her work and her presence.A gentle closing tribute to a woman whose life reminds us that love is something we inherit and something we choose every day.To listen to more reflections and conversations from Season One, subscribe to Meet Me at the Highland on Apple Podcasts, Spotify, and Substack.Share your own reflections and legacy stories with #MeetMeAtTheHighland. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit meetmeatthehighland.substack.com

Dec 3 · 1h 14m

In this conversation, Gabrielle Wyatt and Dr. Gail Parker explore love as a living inheritance and a life practice. They dive into the ways lineage shapes us, how rest and stillness help us return to ourselves, and why awareness is essential for healing and belonging. Dr. Parker reflects on the women who formed her, the lessons carried from her father’s service as a Tuskegee Airman, and the power of breath and restorative yoga to support emotional clarity and nervous system repair. Together they explore what it means to live with intention, to listen to the body, and to dream freely as part of a healing legacy.⏱ Chapters[00:00] Welcome and intention of the Highland[02:15] “I am the daughter of…” grounding in lineage[04:05] Early lessons and the love that shaped her[07:40] Growing up in Detroit and learning community[12:50] What the body remembers and how rest supports healing[17:22] Rest versus sleep and listening for the body’s signals[22:10] Restorative yoga and the nervous system[27:50] Awareness as a daily life practice[31:00] The breath as a doorway into belonging[35:38] Why dreams matter and how imagination guides healing[40:44] Guided breathing practice to return to center[45:18] Belonging, compassion, and seeing each other clearly[50:09] Legacy, lineage, and the stories we carry[56:20] Final reflections on love as a practice🔗 Listen and Subscribe:Apple Podcasts | Spotify | Substack Use #MeetMeAtTheHighland to share your reflections. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit meetmeatthehighland.substack.com

Oct 31 · 4m

Journal Reflection: Becoming the BridgeBefore you write, find a quiet moment. Place one hand over your heart, one hand over your belly.Breathe in slowly for a count of four, hold for two, exhale for six. Whisper to yourself: “I am the bridge. I am the beginning.”Now, reflect:* What stories, teachings, or practices from those who came before you are alive in your work today?* Which quiet, ordinary parts of you (the ones not listed on a résumé or celebrated on social media) are already shaping a collective future?* How are you practicing softness and strategy together, as Chelsea models? Where does that show up in your leadership, your care, your creativity?* If future generations could name one gift you are giving them now, what would it be?Write your responses as if you’re telling a story to someone who will come after you. Let it flow. Don’t edit. Breathe again. Then underline one sentence that feels like a promise you’re making to yourself and to the future.***Dear Chelsea,You are the bridge and the beginning. The memory and the movement. The echo of ancestral prayers and the drumbeat of futures still unfolding.Your legacy reminds us that intergenerational leadership is not about passing the baton—it’s about building the road together, hand in hand, each generation holding a piece of the map. You taught us that legacy is not just what we leave behind—it’s what we live into, right now.You’ve preserved the wisdom of your ancestors, not as history—but as instruction. You’ve rooted your advocacy in truth-telling and creativity, showing us that organizing is not just about resistance—it’s about vision. It’s about becoming.And you, dear one, have become—not in spite of softness, but through it. In a world that rewards burnout and praises the hustle, you chose another way. You chose gentleness. You learned to be tender with yourself, and in doing so, gave the rest of us permission to do the same. You reminded us that preservation isn’t just about policy—it’s about the body. The spirit. The self.You’ve led not from ego, but from ecosystem. From the deep knowing that we are stronger when we are connected. That the path to Black abundance is paved with community, not competition. With care, not control. With stories that speak truth and songs that hold us when words fall short.You’ve reminded us that liberation work requires imagination. That systems don’t shift without new stories. That it is not enough to name the pain—we must also name the possibility.Chelsea, your legacy is already alive in the organizing circles, the storytellers’ pens, the next generation rising in your footsteps—eyes open, hearts wide, spirits steady. You have made it clear that Black freedom is not a dream deferred—it’s a dream designed.Because of you, we know how to lead and listen.Because of you, we know that softness and strategy can coexist.Because of you, we believe in a future where we are not only free—but full.You have given us not just language—but a rhythm. A way to move through the world that honors where we’ve been and declares where we’re going. You’ve shown us that to organize with joy is not naive—it’s necessary. That power by the people, for the people is not a slogan—it’s a sacred responsibility. That Black abundance is not something to earn—it is something to remember.Chelsea, your future is stitched with stories and strategy. With softness and strength. With communities standing ten-toes down in their power and possibility.Thank you for becoming gentle with yourself, so that legacy could move through you, not in spite of you.With clear eyes, full hearts, and hands ready to build, we step forward with you to dream in public with joy and power.Until we meet at the Highland - sending love,The Future ChelseasThis is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit meetmeatthehighland.substack.com

Oct 29 · 53m

In this conversation, Gabrielle Wyatt and Chelsea Miller explore legacy as a living act—claiming authorship of our stories, organizing creatively, and centering rest, stillness, and joy as practices of freedom and sustainability. Chelsea reflects on lessons from the front lines, honoring history while building new blueprints, and the audacity required to move our communities forward together.⏱️ Chapters[00:00] Welcome + intention of the Highland[02:05] “Who are you the daughter of?” — grounding in lineage[03:36] Defining legacy and worthiness[07:49] Intention, inheritance, and living legacy now[09:30] Stories from her mother and why history keeps us grounded[13:02] Intergenerational leadership at the Highland[17:25] Choosing yourself; authorship over outside expectations[26:00] Storytelling, narrative, and honoring collective abundance[31:59] Visibility and creative acts (Pedestals project)[34:54] Resources we need: capital, collective power, creative organizing[37:37] Audacity and organization as practice[44:54] Carrying threads forward: creativity and stillness[47:05] A weekly practice—protected quiet time to dream[50:19] “Because of them… Because of me…” closing reflection🔗 Listen & Subscribe: Apple Podcasts | Spotify | SubstackUse #MeetMeAtTheHighland to share your reflections. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit meetmeatthehighland.substack.com

Oct 3 · 3m

Journaling Reflection: Returning to the VillageThis week on Episode 5 of Meet Me at the Highland™, Dr. Key reminds us that freedom is not theory—it is practice. It is the rooms we clear, the tables we extend, the doors we leave open behind us.After you listen to this week’s episode, find a quiet place.Close your eyes and breathe in for a count of four, out for six. Repeat until your body softens.Ask yourself:Whose brick made space for me to stand here?What is one small act I can offer today that strengthens the village—sharing a resource, making an introduction, buying from a local founder, checking in on a neighbor?If I am a living legacy, what is my contribution to the blueprint?When you finish, write one sentence: “Because of them, I can… and because of me, we will…”Let these words be your offering to the collective future.Until we meet again at the Highland - sending love,Gabrielle****Dear Dr. Key,In this moment of tectonic shift—where the world feels like it’s holding its breath, waiting to exhale something new and necessary—your legacy whispers a steady truth: We’ve been here before. And we know the way.You have long walked in the rhythm of that ancestral knowing. You’ve always been in conversation with the earth. You taught us that stillness is not stagnation, but strategy. That rest is a radical rite. That nature is not only our refuge, but our greatest teacher. You showed us how to sit by water and wait. How to listen to the wind and remember. How to move like trees—grounded, but reaching.While so many raced toward extraction, you slowed us down to remember. You said, Pause. Listen. The land and ancestor will tell you what to do. The people will remind you who you are. And we did. We are. Because of you.We honor you not as the founder of The Village Market, but as the visionary who dares to hold love at the center of systems. Who reminds us that thriving is not the reward for endurance—but our birthright. You’ve never just built a marketplace. You’ve built a movement: a tapestry of cooperative economics woven from the threads of our ancestors’ ingenuity and the bold dreams of those not yet born.In a world conditioned to compete, you turned us toward collectivism. You wove a new economic possibility, not from theory, but from memory. A remembering that our liberation is not a solo act. That community is currency. That when we return to the village, we recover the power of being more than enough—together.What your legacy teaches us is that radical change is not fueled by individualism, speed or spectacle, but by the village, stillness, intention and love. By the kind of quiet revolution that begins when a Black woman listens deeply—to the land, to her lineage, to herself. And isn’t that what love does? It reminds us we are already whole.You are evidence that Black futures must be rooted in love. Not the fleeting kind, but the forever kind. The kind that does not flinch in the face of systemic violence, because it has seen revolution before. The kind that holds the mirror up gently, so we can see our own divinity reflected back.Because of you, we understand that collectivism is not a strategy, but a sacred inheritance. That to gather around the fire of mutual care and shared resources is to conjure a tomorrow our foremothers dreamed while braiding our hair by candlelight.We write this letter not to congratulate you—but to say thank you. For refusing urgency when the village, stillness, intention, and love were required. For choosing the long arc when shortcuts shimmered. For not building platforms, but for building sanctuaries.In you, we see the blueprint of a future that feels like home.Until we meet at the Highland - sending love,The Future Dr. KeysThis is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit meetmeatthehighland.substack.com

Oct 1 · 49m

In this episode, social entrepreneur and visionary founder of The Village Market, Dr. Lakeysha “Key” Hallmon, joins Gabrielle to reflect on the call to gather, dream, and build together.From her beginnings as an educator in Mississippi classrooms to her evolution into an ecosystem builder in Atlanta, Dr. Key shares the lessons that guided her shift from resisting growth to embracing her destiny as a village maker. She reflects on the love that fuels her legacy, her insistence that no one is self-made, and the collective power of ancestral practices of cooperative economics.Dr. Key also opens up about learning to slow down, the spiritual guides who taught her stillness, and the intentionality required to create spaces of healing and joy. At the heart of her story is a call to remember: our freedom is bound to one another, and our legacies are written in community.A conversation on dreaming boldly, building collectively, and choosing love as both blueprint and resistance. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit meetmeatthehighland.substack.com