Meet Tracy Stegall

We had the good fortune of connecting with Tracy Stegall and we’ve shared our conversation below.

Hi Tracy, other than deciding to work for yourself, what else do you think played a pivotal role in your story?
The most important decision I made that contributed to my success was to lead with authenticity and heart. After 32 years in public education—15 as a teacher of writing and reading, 13 as a school principal, and 4 as an executive director—I had the immense responsibility of guiding students, teachers, and entire communities through challenges, including leading a district-wide transition to online learning during the pandemic. That experience reinforced what I’ve always believed: leadership isn’t about authority; it’s about connection, adaptability, and purpose.

In 2023, I made the decision to ‘retire’ from traditional education leadership to chart my own path—on my own terms. I founded All-Inclusive Design, an LLC focused on executive leadership coaching, where I serve as an independent consultant for Front Range BOCES, CDE’s Principal Leadership Institute, and iLearn Collaborative, supporting leaders across Colorado in fostering inclusive, impactful organizations. In 2024, I co-founded Flipside Theatre, a space dedicated to creativity, connection, and community. These ventures may seem vastly different, but at their core, they both stem from my belief in the power of people and the need to create spaces—whether in a boardroom, a classroom, or on a stage—where individuals feel seen, valued, and empowered.

That same philosophy extends to my work as a visual artist. What began as an exploration quickly turned into something more, leading me to show my work in juried exhibitions, collaborate with other artists, and share my creative voice in new ways.

I also remain deeply connected to education as an Affiliate Faculty member at Regis University, where I teach in the Educational Leadership program, preparing future K-12 administrators in Instructional Leadership, Data Analysis, Educational Policy, and Organizational Leadership. Through all of these pursuits, the common thread is independence—I’ve learned that I thrive when I can do what I want, when I want, and how I want. Whether guiding an organization, shaping a performance, mentoring future leaders, or creating a piece of art, my work is always about transformation—helping people, ideas, and communities find their fullest expression.

Let’s talk shop? Tell us more about your career, what can you share with our community?
My career has been anything but linear, and I wouldn’t have it any other way. At my core, I am an educator, facilitator, leader, and artist—and I have spent my life weaving those identities together in unexpected and deeply fulfilling ways.

What Sets Me Apart?
I thrive at the intersection of education, creativity, and leadership. Whether I’m facilitating professional development for school leaders, directing a sketch show, designing a corporate team-building experience, or creating visual art, I bring a unique ability to read the room, foster collaboration, and help people discover their strengths. My background in public education, non-profit leadership, the performing arts, and visual arts gives me a diverse toolbox that allows me to connect with people from all walks of life.

The Path & The Challenges
Getting here wasn’t easy. Early in my career, I was a young teacher stepping into leadership roles, often as the only woman—or the only openly queer leader—in the room. There were moments of resistance, times when I had to fight harder to be taken seriously, and situations where I felt the weight of breaking barriers. But I kept showing up, learning, and building relationships—and that persistence paid off.

In addition to working in education and the arts, I have always felt a deep responsibility to support young people beyond the classroom. After the Sandy Hook shootings, I co-founded Broomfield Buddies, a non-profit dedicated to creating safe, connected spaces for students through peer mentorship and mental health support. The organization fosters a culture where kids know they belong, their voices matter, and they have a network of support. It was born out of heartbreak, but it has grown into a vital community resource that I am incredibly proud of.

Through iLearn Collaborative, I’ve helped shape student-centered school improvement efforts, providing training and leadership development that empowers educators to leverage technology and innovative practices to meet students’ needs. At Flipside Theatre, I’ve co-created a space where people can take creative risks, find joy, and build community.

In recent years, I have also embraced a new artistic journey, exploring the world of visual arts—specifically using alcohol ink on glass and other non-porous materials. What began as a creative outlet has become a deeply fulfilling practice, one that requires me to approach art with a beginner’s mindset. I was honored to be selected for the juried show Prismatic at the Boulder Dairy Center for the Arts in 2023, and my work has been featured at Boulder Pridefest. I’ve also collaborated with local artist Jeanne Mitchell, and some of our pieces are currently on display at Arts Off Center in Superior. Just like in improv and leadership, my art is about embracing uncertainty, following instincts, and finding beauty in unexpected moments.

I’m incredibly proud of:
Currently empowering educators and leaders through my private executive coaching and work with iLearn Collaborative and BOCES, helping them navigate change and innovate in their schools.

My work as a Principal and Assistant Principal in the Boulder Valley School District, leading complex change efforts in PreK-8 schools for over a decade.

Leading the Thompson School District as the Executive Director of Teaching and Learning into the fray of the pandemic, navigating unprecedented challenges while ensuring students and teachers remained supported and engaged.

Helping shape the next generation of school leaders as an Affiliate Faculty member at Regis University, where I teach courses in Instructional Leadership, Data Analysis, Educational Policy, and Organizational Leadership for aspiring K-12 administrators.

Founding Broomfield Buddies, ensuring that young people feel supported, valued, and connected to their community.

Building Flipside Theatre with my amazing co-founders, creating a vibrant artistic hub that fosters creativity, inclusivity, and laughter.

Bridging the gap between corporate, education, and the arts, proving that the skills of improv—adaptability, collaboration, and trust—are invaluable in any setting.

Expanding my artistic identity, embracing visual arts alongside performance, and finding joy in experimentation and collaboration.

Lessons Learned & What I Want the World to Know:

Embrace the detours. My career has evolved in ways I never expected, but every turn has shaped me into the leader I am today.

Community is everything. Surround yourself with people who challenge, inspire, and support you. No one does this alone.

Creativity and leadership are deeply connected. Whether you’re in a boardroom, onstage, or in front of a canvas, the ability to listen, adapt, and build on ideas is a game-changer.

At the end of the day, my story is about taking risks, embracing change, and building spaces where people feel seen, heard, and empowered. That’s the heart of everything I do—whether in education, non-profits, the performing arts, or visual arts.
I frequently turn to poetry to support my work in leadership. Two poets stand out.

David Whyte’s Sweet Darkness reminds me:
“…anything or anyone
that does not bring you alive
is too small for you.”

And from Mary Oliver’s Don’t Hesitate:
“Joy is not made to be a crumb.”

Any places to eat or things to do that you can share with our readers? If they have a friend visiting town, what are some spots they could take them to?
If my best friend were visiting, I’d make sure they experienced the best of what makes this area so special—amazing food, beautiful scenery, and unforgettable experiences. We’d start with breakfast at Lucile’s in Longmont, where the beignets and chicory coffee set the perfect tone for a great day. While in Longmont, we’d visit Cheese Importers, an absolute must for any foodie, with its vast selection of cheeses and European market vibes.

For an iconic Colorado stroll, we’d hit Wash Park in Denver—it’s the perfect place to soak in the sunshine. Then, we’d explore Pearl Street Mall in Boulder, stopping at some of my favorite spots: The Spice Shop for incredible seasonings, Rebecca’s Apothecary for herbal delights, The Peppercorn for the ultimate kitchenware collection, and Piece, Love, and Chocolate because—well, chocolate.

For meals, we’d indulge in dinner at Rioja on Larimer Square, an absolute Denver classic. Happy Hour at The Corner Bar in Boulder would be a must, and lunch at John’s Table in Louisville is always a treat. We’d also do a wine tasting at Balistreri Vineyards, followed by wine shopping at Public Wine in Lafayette, where Doug Wargo curates an incredible selection (and I’d geek out a bit since I’m studying to be a Sommelier).

Of course, no trip is complete without visiting Red Rocks—whether for a concert, a hike, or just to take in the breathtaking views. We’d also head up to Estes Park, where I have family ties, and have lunch or brunch at Bird and Jim, a spot that perfectly captures Colorado’s mountain charm.

For a touch of culture, we’d visit Dushanbe Tea House, a stunningly intricate gem in Boulder. And, since movement and creativity are big parts of my life, I’d take them to a dance class at Alchemy of Movement on a Tuesday with Carolyne Rideg—it’s an incredible way to connect with music and energy.

To cap off the trip, we’d spend a night at Flipside Theatre, catching an improv or comedy show, maybe even featuring one of my teams, Hello Comrade or Highbrow Fartz. It’s the perfect way to wrap up a week filled with laughter, adventure, and some of the best that Colorado has to offer.

Who else deserves some credit and recognition?
No one builds a meaningful life or career alone, and I am incredibly grateful for the people who have shaped, supported, and challenged me along the way.

There are so many people who have played a role in my journey, but first and foremost, I want to recognize Christina McCann, my partner, whose unwavering support and love fuel all my endeavors. Her belief in me makes every challenge more manageable and every success more meaningful.

I also want to honor Gayla Lindquist, the first principal who hired me in Boulder Valley School District as a young teacher. She saw something in me and nurtured it, and her recent passing on January 19, 2025, has only deepened my gratitude for her guidance. Dr. Ellen Miller-Brown was another pivotal figure—she believed I should be a principal and stood by my side as I navigated leadership in a conservative community as an out lesbian administrator. As a Principal, I had the privilege of mentoring—and learning from—Erin Hinkle and Dr. Bryant Shaw when they served as my Assistant Principals. I’m incredibly proud of the work we accomplished together and love seeing them thrive as Principals!

And I can’t talk about my journey without celebrating Miguel Hernandez, Anders Lankford, Marc Steuben, and Jenny Remack, my fellow co-founders of Flipside Theatre. Together, we took a leap into a gorgeous creative abyss, and the ride has been exhilarating.

Finally, I circle back to Christina, because none of this would be possible without her steadfast love, encouragement, and willingness to dream alongside me.

Website: https://sites.google.com/view/tracy-j-stegall-digital-portfo/home?authuser=0

Instagram: https://www.instagram.com/tracy.stegall.7/

Linkedin: https://www.linkedin.com/in/tracy-stegall/

Facebook: https://www.facebook.com/tracy.stegall.7

Other: https://www.superiorimprov.co/about