Alright – so today we’ve got the honor of introducing you to Tamyra Gordon. We think you’ll enjoy our conversation, we’ve shared it below.

Alright, Tamyra thanks for taking the time to share your stories and insights with us today. Are you happier as a business owner? Do you sometimes think about what it would be like to just have a regular job?

I walked into Pilates today at 7AM. Sat on my reformer and stretched. Halfway through the class I looked up and realized I was the youngest person in the room. Out of the window I saw a boy about my son’s age running into Starbucks to seemingly pick up a before school treat and his mother’s coffee. On the way home I sit patiently behind school busses and drop off lines while mentally preparing for my 9AM zoom meeting.

My husband often says “you live like a retired person”. Someone who has intentionally found a way to be right on the outskirts of systems we’re told to be a part of (school, work, the American dream)…
Five years post pandemic we’ve built a business that allows us to work from home or anywhere
We homeschool our son and have slowed down our mornings
We prioritize our health and family time and make our work and business fit around that
I workout with the retirees during school & work hours

And I am so grateful. I appreciate what owning a business has afforded me and my family. I am grateful for how much time I get to claim as my own. The tastes of freedom we’ve had over the last few years makes the hard times worth it.

But let me tell you…it’s hard.

Am I happy – yes. Am I happy as a business owner – not always. Have I wanted to throw it all away, give up and do the more conventional thing- all. of. the. time.

My husband and I acquired a business while starting two other businesses – why, I don’t know. But we acquired a business that was doing well on the outside and was a legacy to the community, but came with head, heart and financial aches we could not prepare for.

We moved fast trying to take advantage of this moment and gift we were given of abundance and stewardship. We lead with our hearts and being new to business owning and needing help, we trusted people who weren’t trustworthy. We gave to takers. We exposed ourselves and were taken advantage of.

AND…

We traveled the world. We were able to hire our family members at one point 80% of employees were in our family tree. We experienced a freedom in time, thought, energy and resources that we didn’t know was possible for us. We slowed our mornings, we decided to school our son at home, we reinvented life in a way where school and work fit around our family. We leaned into possibility and imagination in ways that we would not have working in a 9 – 5.
Exhaustion supersedes imagination when…
you’re commuting 2hrs, preparing for school, board meetings and after school activities. When the 5 mins you may have gotten to yourself in the car to play that music you need to amp up your day, is overtaken by a run in with a disgruntled parent or PTA member upset you’re not doing enough, it’s hard to dream of a life you really want and would be excited by. There’s no space for it.

Owning a business gave us s p a c e.

Space to dream, to reimagine, to learn and unlearn, to reconsider all the choices we’ve made up until that point and begin to make new ones. It gave and continues to give us perspective into what is most important to us and to prioritize those things over everything else.

And like with every choice, there’s a trade-off.

The conventional life, 9 – 5, school drop off and pick up, long commutes, limited family time, comes with a trade off of time and room to imagine. Business life comes with the responsibility of making payroll every two weeks, even if that means you don’t get paid to pay your staff, it means taking out more debt after buying your first house to make ends meet, it means trusting you can figure it out and gameplanning with your spouse while playing jengo and Uno on the floor with your son on a Monday morning before the day starts.

There are moments when that lure of normalcy calls to you. Where I wonder if we are doing the right things for our son, where the school functions and parent meetings seem like a right of passage we’re missing out on, where the challenges of the business seem so insurmountable that you want to throw in the towel and attempt to start over.

Then we remember what this hard choice has afforded us
Time to fly back to the East Coast to be with our grandmother as she transitioned
Moments to witness our son be excited about learning and care for him when he’s challenged
Opportunity to pack up and work from all across the country
Curiosity from our family and friends about what we are navigating and how they can learn from it
So much more laughter, hugs, shared tears, use of our home, insight into each other’s thoughts
Feelings of purpose and alignment to something beyond ourselves

Who knows what our next season will bring, but this season we are swimming in gratitude and trust that if we make choices rooted in love, purpose, and spirit that we will be guided and protected along the way.

Great, appreciate you sharing that with us. Before we ask you to share more of your insights, can you take a moment to introduce yourself and how you got to where you are today to our readers.

I’m Tamyra Gordon—an educator, curriculum designer, historic preservationist, and founder whose work sits at the intersection of cultural legacy, community empowerment, and systems change. With over 18 years in nonprofit leadership, I’ve led national workforce programs like Year Up, America Needs You, and Rutgers Future Scholars. But my path has never been about titles—it’s always been about building spaces where Black communities are seen, resourced, and remembered.

Through Greenwood Seneca, a company I co-founded with my family, we own and operate entities like Seneca Real Estate Services and The Brick TV, allowing us to support community led infrastructure projects, capacity building, and media storytelling under one unified vision. I also launched Your Legacy Tours, a public history experience recognized by the National Park Service, that brings descendants and community members to sites of enslavement with joy, dignity, and reverence—creating sacred reconnections that traditional tourism often overlooks.

My services range from curriculum strategy and program development to narrative design and nonprofit advising. Whether revising financial literacy courses for young people, co-leading QTBIPOC fellowships like CoFED’s Just Leader Fellowship, or facilitating equity-centered historic redevelopment in places like Las Vegas’ Historic Jackson Avenue, I bring a uniquely holistic, healing-centered, and culturally grounded approach.

What sets me apart is my Sankofic lens: I don’t just teach history, I live in conversation with it. I’ve designed Black homeschooling curricula rooted in ancestral wisdom, built tools for nonprofit sustainability, and helped organizations reimagine how they connect with community. I lead with love, spirit, and strategy—making room for alternative ways of learning, living, and leading.

What I’m most proud of is helping families and institutions embrace the power of legacy—not as a weight, but as a foundation. My mission is to help others reclaim their stories and restructure the systems that impact our lives. I want potential partners to know that when you work with me you’re investing in transformation with both heart and history at the center.

Are there any books, videos, essays or other resources that have significantly impacted your management and entrepreneurial thinking and philosophy?

Yes—some of the most impactful resources that shaped my thinking aren’t traditional business books at all, but historical fiction and narrative works that reframe how we approach truth, power, and humanity. Novels like The Water Dancer by Ta-Nehisi Coates and Happy Land by Dolen Perkins-Valdez gave me permission to imagine beyond the archive. These authors blend documentation with imagination to bring dignity, possibility, and fullness to Black lives often reduced to footnotes. Their work reminds me that leadership, like history, isn’t just about facts—it’s about story, presence, and emotional intelligence.

This lens shapes how I build programs and lead organizations. Whether I’m revising curriculum for opportunity youth, designing worldschool lessons for my son, or facilitating Your Legacy Tours at sites of enslavement, I use narrative strategy to humanize, not just historicize. I also draw on my own work, like Legacy’s Lyric, a creative data report for Blavity.org that used music, cultural references, and narrative storytelling to make funding and entrepreneurial trends digestible and deeply resonant for Black audiences.

These resources have taught me that people remember stories, not spreadsheets—and that as an ancestral steward, my job is to make the work feel rooted, real, and reachable.

What’s a lesson you had to unlearn and what’s the backstory?

I had to unlearn the idea that success is about ascending to power, holding titles, or staying on a linear career path. For years, I was chasing the executive seat. I led national programs, managed million-dollar budgets, sat at head tables. But somewhere in that chase, I realized I was becoming fuel for everyone else’s vision—and starving my own.

The truth is: I wanted to be more than a nonprofit leader. I wanted to be a mother, a homeschooler, a baker, a carpenter, someone who made beautiful things with her hands and taught her son how to build, imagine, and question. I had to grieve the version of me who was addicted to productivity and status. And then, I had to reinvent.

I’ve since built Greenwood Seneca and Your Legacy Tours not just as business ventures, but as extensions of a life I want to live—one that honors my ancestors and allows me to be fully human. The biggest lesson I’ve learned is that you can reinvent yourself as many times as you need. There’s no blueprint for a life well-lived. There’s just alignment. The real work is choosing to create a life you’re fueled by, not drained by—one rooted in vision, values, and joy.

Contact Info:

• Website: https://www.greenwoodseneca.com
• Instagram: @tamyra_gordon
• Linkedin: https://www.linkedin.com/in/tamyragordon/

Image Credits

John Jo Photography
Ish Picturesque
Britney Jean Photography