Dr. Dena Simmons: The Soil We Cannot See

“Because of them, I can dream. Because of me, I can make my dreams come true.”

What happens when the most important soil we tend cannot be seen?

In Season 2, Episode 3 of Meet Me at the Highland™, Gabrielle Wyatt sits with Dr. Dena Simmons, founder and executive director of LiberatED, for a conversation about the emotional ground beneath education, leadership, wellness, and justice.

Dena reflects on the strength and perseverance she inherited from her mother, the emotional weight she learned to swallow as a young Black girl, and the experiences that forced her to redefine success. From leaving Yale after being bullied to building work rooted in radical love, healing, and justice, she shares why wellness cannot be separated from culture, context, community, or power.

Together, Gabrielle and Dena explore what it means to protect your spirit without abandoning the work, to build care alongside the people it is meant to serve, and to leave the next generation with more than ambition and endurance.

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, with the vision of creating a world where all children can live, learn, and thrive in the comfort of their own skin. Dr. Simmons writes and speaks nationally about the intersection of social and emotional learning, justice, and healing.

03:43 — The Lineage That Grounds Her
Dena calls in her mother and reflects on the perseverance, love, and liberation that continue to shape how she moves through the world.

07:29 — Choosing Joy and Living Fully
She shares how her twin sister’s chronic illness and her own health journey deepened her appreciation for life and her ability to choose how she wants to live.

09:57 — Redefining Wellness and Success
Walking away from Yale after being bullied forced Dena to expand success beyond institutions, accolades, and endurance to include therapy, family, emotional processing, laughter, and care.

15:28 — Self-Preservation as Community Preservation
Dena explains why protecting herself is inseparable from building community, seeking support, and refusing to remain inside environments that are poisoning her.

21:54 — Changing Systems From the Ground Up
She considers how children, educators, and communities can help shift systems by creating broader definitions of success rooted in humanity and collective care.

24:50 — Building Trust Through LiberatED
Dena describes co-creating with educators and students, refusing to dilute the organization’s justice-centered language, and creating spaces where existing gifts and wisdom can flourish.

36:35 — Courage, Integrity, and Walking Away
She reflects on the experiences that taught her to stop performing inside institutions that harmed her and to choose work aligned with her values.

47:47 — Freedom You Cannot Unsee
Gabrielle and Dena explore what becomes possible when Black women experience freedom beyond constraining systems and recognize what they can build together.

54:37 — The Practices That Keep Her Whole
Dena shares the practices that support her well-being, including movement, therapy, meditation, acupuncture, Yoga Nidra, community, and listening to her body.

1:02:27 — Why Wellness Requires Justice
She explains why social and emotional learning, mindfulness, and wellness practices can reproduce harm when they are separated from culture, power, and an anti-racist lens.

1:08:04 — Building an Ecosystem of Care
Dena shares her vision for asking educators and students what they actually need and building care from their answers rather than imposing it from above.

1:12:11 — Dreaming and Making Dreams Real
She closes the conversation by honoring those who made her dreams possible and affirming her own power to bring those dreams to life.

• Success must include wellness, family, emotional processing, laughter, and care—not only achievement or institutional recognition.

• Self-preservation is also community preservation; people need relationships and support to remain whole.

• Care cannot be separated from culture, context, history, identity, and power.

• Wellness practices can reinforce harm when they teach people to quietly endure unjust conditions.

• Trust is built by listening to communities, honoring what they say they need, and acting on what is heard.

• Values-aligned leadership sometimes requires refusing to dilute your language or remain inside institutions that harm your spirit.

Dena expands success beyond accolades, prestigious institutions, and the ability to endure. Her definition includes wellness, family, emotional honesty, therapy, laughter, rest, and the ability to care for herself while pursuing meaningful work.

Dena describes self-preservation as community preservation. Protecting yourself requires recognizing toxic conditions, building supportive relationships, and allowing community to provide what you cannot always provide alone.

Dena argues that wellness, mindfulness, and social and emotional learning cannot truly care for people without considering culture, identity, history, and power. Without that context, practices presented as healing can protect privilege and teach people to endure injustice more quietly.

LiberatED is an organization founded and led by Dr. Dena Simmons that centers radical love, healing, and racial and social justice in education and social and emotional learning. Its work supports the mental health and well-being of students and educators.

The soil we cannot see is the emotional and relational ground beneath our homes, schools, workplaces, and communities. It is shaped by what people are encouraged to express, what they are taught to swallow, and whether the care offered to them recognizes their full humanity.

Dena reminds us that the future is shaped not only by what we teach or build, but by the conditions we create around the people coming after us. Tending that ground requires wellness with justice, care with context, and the courage to listen—and then act.

New companion letters will be released weekly following this conversation.

What the Next Generation Inherits
A reflection on the emotional and relational ground we are preparing for the generations coming after us.

A Love Letter to the Future Dena Simmons
A letter about trusting the body, expanding our definitions of success, and continuing to choose integrity, wholeness, and freedom.

The Care We Seed Forward
A deeper reflection on why wellness without justice is not care—and what culturally grounded, power-aware care requires.

What We Leave in the Ground
A closing reflection on the emotional climate, practices, and possibilities the next generation will inherit from us.

Connect with Dr. Dena Simmons

Website: denasimmons.com
LiberatED: liberatedsel.com
Instagram: @denasimmons
Twitter/X: @denasimmons
LinkedIn: Dena-Simmons

Connect with Meet Me at the Highland™

Full episode and companion content: meetmeatthehighland.substack.com
The Legacy Studio: visit here
Instagram: @meetmeatthehighland
YouTube: @MeetMeatTheHighland

About the host

Gabrielle Wyatt is an investor, futurist, strategist, and the founder of The Highland Project, an ecosystem designed to build and accelerate multigenerational wealth in Black communities and beyond. Her work sits at the intersection of legacy, rest, radical possibility, and community wealth creation. She is the creator of Meet Me at the Highland™ and the writer behind The Stillness Ranger. Gabrielle is an emerging voice on rest as a leadership strategy, legacy as daily practice, and visioning as political, cultural, and spiritual technology.

Credits

Meet Me at the Highland™ is hosted and created by Gabrielle Wyatt. Executive Producer and Writer: Keena Williams. Meet Me at the Highland™ is a production of The Highland Project.

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