We caught up with the brilliant and insightful Judy-Ann Denton-Green a few weeks ago and have shared our conversation below.
Hi Judy-Ann, thanks for joining us today. It’s always helpful to hear about times when someone’s had to take a risk – how did they think through the decision, why did they take the risk, and what ended up happening. We’d love to hear about a risk you’ve taken.
In 2002, while still a student at Wilberforce University, Ohio, I made a decision that would mark the beginning of my journey of exploration into the unknown. With no money for flights or trains, and a strong desire to meet my father’s sister for the first time, I boarded a Greyhound bus bound for Texas. It was my first solo road trip, and it would take me 28 hours, stopping in nearly every city along the way. I had no map, no detailed plan, and hardly any funds to my name. I was nervous and anxious about what I would find or if I would even make it there. But it was a risk that I was willing to tackle. I didn’t know the people whom I would meet or what the journey would bring, but I felt that pull to take a leap of faith.
The journey was grueling; endless hours on the bus, each stop in a new city, with a new set of restrooms, a new set of faces, and long queues that brought on more uncertainty. However, I found much comfort in reading-my way of traveling to settings that opened my mind to new cultures, camouflaging reality, and redirecting hope.
In the middle of my escape into the pages of Dr Maya Angelou’s “I Know Why The Caged Bird Sings,” a clatter and chorus of voices broke through my solace. The bus broke down. This was 11 hours into the journey. The unplanned stop caused a stir as it was nearing nightfall and we were nestled between mountains, on an isolated dusty country road with nature as our only company. There were no signs of other human life for hundreds of miles.
As our bus driver asked us to vacate the bus for safety, doubts began pooling with weariness in my stomach and dread set in. Up to this point, my book was my company, but now I needed more. One thing that I have learned under my grandfather’s wise tutelage is that there is safety in numbers, so prayed for courage and then began studying the masses for a safe person. After what seemed like decades I struck up a conversation with two sisters traveling to Houston, sharing stories, snacks, laughter, and a blanket. After two and a half hours we got a replacement bus, and I had bus buddies who made the rest my journey unforgettable.
Today, I treasure those hours for the invaluable lessons I gained, lessons I never would have learned if I hadn’t taken the risk: reaching out, the power of connection, and trusting the process. My aunt, whom I met for the first time on that trip, is now my confidant and sage. She is one of the best human relationships I have on earth—my yin to my yang. I also got to spend quality time with my other aunt, whom I hold dear, and the bond we formed during that time is something I’ll cherish forever.
Simon Sinek often talks about investing in “relationship currency,” and this trip was my first lesson in that. I understood that true wealth in life is found in the bonds we create and the risks we take to connect with others. That journey to Texas, though uncertain, reshaped me. It taught me that taking risks isn’t just about the destination, it’s about who you meet and how you grow along the way.
Since then, I have lived on two other continents, and it is that early experience of uncertainty and connection that has shaped my outlook. I have grown to embrace risk, to find courage in unfamiliar places, and to invest in relationships because in the end, it’s not just where you go, but the people whom you meet and the way how they shape you that truly matters.
What risk are you willing to take to move closer to your own goals?
Awesome – so before we get into the rest of our questions, can you briefly introduce yourself to our readers.
“Repeat your 6 times tables. Form a straight line. Let’s go over this again. Are You Ok?” These were the words I echoed on my way home from elementary school daily. Since the age of 5, I have been role-playing school with my friends, and can you guess who played the role of the teacher? Me. After 24 remarkable years in education, I have traversed and taught on three continents, empowering thousands of students to dream big, implementing literacy initiatives across schools, dedicating my life to the transformative power of learning, and coaching a plethora of educators whom I believe will take on the baton. This current academic school year marks a pivotal moment of pause—a deliberate step back to write, reflect, and give back to the communities that have shaped my professional journey. I am proud to serve as a Circle Leader for LeanIn, a parent volunteer at our youngest child’s elementary school, a dedicated IE University Parent Ambassador, a NEASC School Accreditation Visitor, and a DEIB and Culture Taskforce member for NEASC.
I would liken my career to a symphony composed of diverse roles and enriched by profound experiences. From serving as a Head of Edwin Allen’s Student Council in high school to dorm leader in university, from Professional Development Leader to designing curricula, from guiding pastoral care to leading teaching and learning initiatives, from embedding literacy across the school to coaching teachers to teach from the heart, I have approached each position with a commitment to excellence and a deep understanding of educational dynamics as well as to show credence to my teachers who illuminated the true meaning of dedication, compassion, resilience, and purpose
I am grateful to have been honored with awards recognizing outstanding leadership and educational innovation. This resulted in a positive impact on students’ achievement as well as staff development and was symbolic of our school being selected for the coveted Race to the Top Award. Other acknowledgements include Teacher of The Year Award, and the award for Outstanding Leadership, Organization, and Preparation. My work in education has taken me from serene school rooms to the Sheikh’s palaces, from cafeterias to conferences, and from heart of the community to the grandeur of global events.
Yet, my greatest pride lies not in accolades, but in the lives transformed through dedicated teaching and mentorship. The note below (printed with permission), recently sent by one of my now adult students, reminded me of my ‘Why.” It reinforced the reason that I became an educator — to be a powerful instrument of transformation, shaping lives and empowering students to reach their full potential:
Dear Ms Denton,
Being a student of yours shaped my future in the best way possible. You truly loved, supported, and empowered us all, and your positive mantras have stayed with me to this day.
You focused on experiential learning rather than the traditional nose-to-book. Challenging us by pushing us to strive for our dreams, and not be stifled by our self-limiting beliefs, or negative feedback from external forces. I will never forget how you would sing to us and dance with us in class and tie those experiences into our day-to-day lessons.
You were such a kind soul, and through the bullying I experienced, you were always there for me, without fail, to pick me up, dust me off, and remind me of how worthy I am.
I often reminisce and understand how blessed I was to have you as a teacher and a role model. You taught me how to dream BIG, and now I will do the same for my children.
Thank you, Miss Denton, I appreciate you more than you know.
This year of reflection is not an ending, but a new chapter. It’s an opportunity to distill decades of experience, to give voice to the lessons learned across three continents, and to contribute meaningfully to the educational community that has deeply shaped me. I aim to share insights, inspire future educators, and continue the work of nurturing potential in its most profound sense.
As I get ready to embark on this new journey with Dr. Ava Eagle-Brown and publish my first book on teaching and learning, I am excited to continue to learn, grow, and live on purpose. My journey has always been about more than just teaching—it’s about creating environments where learning transforms lives, and where educators and students alike can discover their most authentic selves and greatest potential.
How will the footprints you are leaving behind help in guiding the path for others?
We’d love to hear a story of resilience from your journey.
Fresh out of “The Mico.” now known as Mico University College, widely regarded as a prestigious training institution that has produced the best teachers across the globe, I was living a life many would envy. I had a well-paying job, shared a beautiful home with my cousin in one of Kingston’s most upscale neighborhoods—the capital city of Jamaica, or “town” as we affectionately call it—and felt a sense of stability that made everything seem to be falling perfectly into place. But life has a way of upending even the best-laid plans.
When my sister experienced a significant life event, I knew my place was with her. I idolize my sister. No! All of my siblings do, she is endowed with beauty and brains and has a heart of gold. Without hesitation, I decided to move to the United States to support her, leaving behind the life I had worked and struggled to build. I took a gap year after high school to work, and I saved every dime to pay off my first year of college at “The Mico.” Back then my parents advised me to choose another profession, but I was determined to teach. After several tearful encounters and negotiations, I promised Mom, Dad, and Grandpa that I would work for a year, save enough to cover the cost of my first year of college and if I did that, then I was free to pursue education and they would finance the rest of my college tuition. I proved myself to my parents, and it was truly fulfilling to start working after my graduation.
I had dreams of pursuing my graduate degree at The University of the West Indies or Northern Caribbean University, eating Devon House Ice-cream, and continuing my monthly visit to one of my favorite spots- One Love Cafe at the Bob Marley House in Kingston. Now, here I was dismantling my life and starting anew in Ohio. I felt both joy and trepidation—while I was excited to spend more time with my sister, I was heading into the unknown-leaving my sure for the unsure. The unknown was frightening, and the uncertainty ahead scared me. My sister and I agreed that I would complete further studies while taking care of my niece and nephew during the day. At the time, it seemed like a seamless plan, but I quickly realized I had not fully thought it through.
Having graduated from The Mico debt-free, I was determined not to burden my parents with the cost of this degree. But here I was, in a new country, unsure of where the money would come from to fund my studies. With no clear path ahead, I enrolled at Wilberforce University on what could only be described as “a wing and a prayer.”
Wilberforce was more than just an educational institution; it became the place where I truly understood resilience, support, and sacrifice. I wasn’t just managing the demands of academia while juggling morning school runs, I was also learning to navigate life’s challenges with faith and determination.
My sister is a gem. Our sisterly bond was unbreakable; I wore the best clothes, had a steady salary, and ate the best food. Yes, my sister even took on an extra university class on weekends to help cover my school fees. Through it all, I discovered the power of perseverance and the strength found in relationships forged.
At Wilberforce, I honed in on skills that would help me navigate my future. I learned how to apply for scholarships, how to write grants, and how to take ownership of my educational journey. I spent countless hours in the library, researching scholarship opportunities, and developing strategies for securing funding. I wasn’t just going to school; I was learning how to create opportunities for myself, even when it seemed impossible.
Living an hour away from campus, I was faced with the challenge of navigating transportation as there was not a direct public transportation link from home to school. After struggling for a month, networking provided me with the opportunity to carpool with a group of amazing women. Through those shared rides, I learned the power of community and mutual support. We were more than just classmates—we were a network, a sisterhood, bound by a shared experience of ambition, sacrifice, and dreams that reached beyond the horizon. Those lessons learned from our friendships have lasted, and today, they are still a source of strength in my life.
Looking back, I can see that Wilberforce University gave me far more than an education. It gave me the tools to face the world with confidence, knowing that resilience isn’t about having all the answers but more about having the courage to take the next step, even when you don’t know how you’ll make it. It was through this experience that I learned to navigate life across continents, build relationships that would last a lifetime, and grow into a version of myself I hadn’t yet imagined.
Now, in 2025, after 24 years in education, I’m preparing to step into a new chapter of my life. With the skills I developed at Wilberforce and the unwavering support of educators and mentors like Ms Pat Copely, Ms Ann-Marie Leigh, and Dr McIntosh I am proud to announce the publication of my teaching and learning book. What once seemed like an impossible dream is now a reality, and I’m ready to embark on this next journey.
Join me as I step into this new dimension. If there’s one thing I’ve learned along the way, it’s that sometimes, all you need is a wing and a prayer to make it through—and to soar.
What is preventing you from soaring today?
What’s been the most effective strategy for growing your clientele?
As a daughter of the late 70s, this question makes me chuckle. My journey has taught me that the key to growing my clientele has been about building relationships that last, rooted in authenticity, and purpose. Investing in the friendships that I have forged along the way is essential. For me, it’s not just about networking for the sake of business; it’s about genuinely connecting with people- learning their names, their interests, and their goals.
My learning journey has shown me the necessity of taking the time to understand who someone is, and their “Why”, rather than just what they do, and this approach has led to more meaningful relationships. There is so much more we can learn about others than what they do.
How do you normally introduce yourself or what questions do you normally ask to get to know someone? I genuinely like meeting people and so I research questions to ask all the time. Here are a few simple ones:
“What motivated you to attend this event?”
“How would you describe…?”
“What’s been the highlight of your experience so far?”
“How did you become interested in this area?”
I have a note on my phone where I have documented everyone whom I have met over the last ten years. I have categorized them with small notes about each person. Recently, I updated it to include the date and place we met. This system allows me to keep track of connections, reflect on past interactions, and truly value the relationships that have shaped and is shaping my journey.
During the late fall of 2024, I attended events like Abu Dhabi Business Week and the Global Media Congress. I led a session at the Dubai GESS Conference and attended the Women in Education Breakfast event. However, what truly stood out wasn’t just exchanging business cards or talking about roles. It was about engaging with people on a deeper level and having ‘Small Talk.” I had an experience that reinforced this approach: I met a remarkable woman at The Global Media Congress in Abu Dhabi. We were standing observing the interaction of those waiting in line to meet Mo Gawdat (the highlight of my week). Someone came up to her, exchanged names, and immediately asked, “What do you do?” She responded, “I don’t know you well enough to share that personal information. Let’s talk first, take me out to buy a cup of coffee and then I’ll share.” Immediately, I felt my dopamine levels rise. I was overjoyed to hear someone else share my passion for prioritizing the person before their professional title.
This encounter reminded me that relationships matter and that there’s so much more to discover when we intentionally seek to learn who someone is, not just what they do.
So what has been the most effective strategy for growing my clientele? It has been building authentic relationships, ones that create trust, foster loyalty, and encourage long-term connections. When you train your mind to be genuinely interested in others, your following will grow—not because of what you offer, but because people feel seen and valued.
What strategies have worked best for you in building strong relationships? What will you start or stop doing to enhance your relationships?
Contact Info:
- Instagram: @teachlearnspeak
- Linkedin: https://www.linkedin.com/in/judy-ann-g-4544321a0
- Youtube: youtube.com/@TeachLearnSpeak