We’re excited to introduce you to the always interesting and insightful Sierra Dockery. We hope you’ll enjoy our conversation with Sierra below.
Sierra, thank you so much for joining us today. Let’s jump right into something we’re really interested in hearing about from you – being the only one in the room. So many of us find ourselves as the only woman in the room, the only immigrant or the only artist in the room, etc. Can you talk to us about how you have learned to be effective and successful in situations where you are the only one in the room like you?
I really appreciate this question, both as a teacher and as the CEO of my company. In the early stages of my entrepreneurial journey, I often chose to stay in my role as a teacher and intentionally didn’t let others know that I owned the company. When I interacted with others, I would speak as though I was simply an employee. At that time, I was hesitant to step fully into my leadership role because behind the scenes I was wearing every hat in the business. When it came to conversations with Directors, Principals, and Superintendents, I often found myself timid and unsure.
That began to shift in 2018 when my mentor encouraged me to travel with her to Ghana, where she was visiting the Cape Coast School for the Blind. During that trip, I met my current life coach, who reminded me of my worth, my accomplishments, and the importance of owning my place at the table as the leader of my company. Until then, imposter syndrome had often taken over, especially since I was frequently the only one in educational spaces who looked like me, and I struggled to respect myself as a leader.
Through consistent life coaching and therapy, I began to do the deeper work—exploring the type of legacy I wanted to leave for myself and my family. I also committed to developing my craft, establishing myself as a subject matter expert, and walking into rooms with greater confidence. Along the way, I returned to school and earned my MBA, sharpened my ability to negotiate and review contracts, and redefined who I am as a leader.
What started with just me has now grown into a full-time agency serving over seven school districts in Illinois, and at one point we were managing thirteen. My journey has been one of growth, healing, and transformation—learning not only how to lead others, but how to first lead myself with confidence and clarity.
Thanks, so before we move on maybe you can share a bit more about yourself?
During the day, I serve as a Teacher of the Visually Impaired, traveling from school to school to provide specialized services for students who are blind or visually impaired. This work includes teaching Braille reading and writing, telling time, touch typing, and essential daily living skills that foster independence. At the same time, I also serve as the CEO of my organization. Recently, we brought on a Chief Operating Officer so that I can begin transitioning out of the classroom and focus more on expanding opportunities for growth. My vision is to build a full staff dedicated to serving school districts while I focus on opening our new therapeutic day school for children and adults who are blind or visually impaired. In the afternoons, that same space will serve as a community center where families, students, and older adults who are blind can come together and find belonging.
The greatest joy in my day comes from seeing both my staff and my students thrive. From a CEO perspective, I get to pour into my staff, watch them enjoy their work, and grow in their careers. From a teaching perspective, I see the daily progress of my students—such as a fourth grader who once struggled with Braille but can now successfully add four-digit numbers. These moments remind me of the impact our work has on student success and independence.
At the heart of our organization, we operate like a family—supporting one another, our students, and their parents. I truly love what we do as an organization, and I am proud to lead a team that brings both skill and compassion to this work every single day.
Looking back, what do you think were the three qualities, skills, or areas of knowledge that were most impactful in your journey? What advice do you have for folks who are early in their journey in terms of how they can best develop or improve on these?
The three qualities that had the greatest impact on my journey were healing, learning to ask for help, and aligning with my purpose. Healing allowed me to grow past old wounds and step into leadership with clarity. Asking for help taught me that pride and ego can become barriers, but humility opens doors to support and growth. And when I truly understood my purpose and connected with my spiritual side, everything in my journey began to align.
The advice I would give to those just starting out is this: do the inner work early. Who you are at your core should reflect in every aspect of your life. When you show up authentically for yourself first, you are better equipped to show up for the world.
Alright so to wrap up, who deserves credit for helping you overcome challenges or build some of the essential skills you’ve needed?
When this question is asked, our natural instinct is to think of one individual. However, when I reflect on my journey and the success I’ve achieved, I have to say it has been my village. Each person in my village has played a vital role in helping me overcome challenges and build the skills, qualities, and knowledge I needed along the way. I’ve come to realize that I could not have done this on my own, and it is the collective support of my village that has made all the difference.
Contact Info:
- Website: https://www.houseoflightllc.org
- Instagram: https://www.instagram.com/house_of_lightllc/
- Facebook: https://www.facebook.com/houseoflightllc
- Youtube: https://www.youtube.com/@houseoflightllc
so if you or someone you know deserves recognition please let us know here.
