Alright – so today we’ve got the honor of introducing you to Judy-Ann Denton-Green. We think you’ll enjoy our conversation, we’ve shared it below.
Judy-Ann, we’re so excited for our community to get to know you and learn from your journey and the wisdom you’ve acquired over time. Let’s kick things off with a discussion on self-confidence and self-esteem. How did you develop yours?
I began learning at the feet of my grandfather, a man whose quiet strength shaped the foundation of who I am. His own father died when he was just a youth, and he quickly stepped into the role of provider, working hard, sacrificing much, and eventually building a life rich in integrity, land, and legacy.
By the time I came along, he had become a pillar in our family. He could walk into any room and negotiate with grace, speak with clarity and purpose, and somehow, always leave with a win-win.
His confidence was born from struggle and forged through experience. I remember him looking me in the eye and saying, “Hold your head high, girl. You come from good stock. Trust in God, He will do the rest.” That stayed with me to this day, and now I know to trust God with my future.
These lessons from my grandfather-Sydney McKinson, became the cornerstone of how I built my confidence and self-esteem.
My father’s story left an indelible mark on my mind. He is the blueprint for confidence-building. Dad worked at Kingston Wharves – faithful, hardworking, and meticulous in both his duties and the way he carried himself.
Like when a steady ship suddenly changes course mid-sea, tragedy struck. His father was rapidly losing his eyesight. So, without flinching, Dad left his secure job at Kingston Wharves, to care for his aging father and pursue farming.
People laughed.
My father traded pens and ties for a machete, progress for protectiveness, and comfort for caregiving. He planted, learned, failed, got up, and kept going. Eventually, he became one of the most respected large-scale farmers in our community. His journey taught me that confidence isn’t loud, no, it’s steady, determined, and often misunderstood at first.
My confidence was stretched and nurtured at Edwin Allen High School, or “Compre” as we fondly called it. As Head Girl, I was entrusted with responsibilities that pushed me beyond my comfort zone. I organized prefect duties, stood at the gate ensuring rules were followed, mentored students, led devotions for the entire school, and found myself growing into someone others could trust.
Whether I was coordinating prefect meetings or mentoring younger students, resolving lunchtime squabbles, or standing before a crowd of my peers with a microphone and shaky hands, those moments planted the seeds of leadership. I realized confidence isn’t the absence of fear, no, it is being fearful but doing it with fear anyway.
And then there was “The Mico,” a place where tradition meets transformation. Walking the halls of Mico Teacher’s College (not yet named The Mico University College in my time), I found more than lectures and textbooks, I found belonging. The lecturers didn’t just teach, they nurtured (special thanks to Mrs. Loftman, and Mrs. Karen Harris). They saw what I could become and spoke to that version of me. They encouraged me to stand taller, speak clearly, and believe more deeply in the power of my voice. It was there that my self-esteem took root, watered by mentors who believed in my potential even when I didn’t always see it myself.
My confidence and self-esteem are not inherited like jewelry, they were modeled, tested, and strengthened over time. From my grandfather’s commanding presence to my father’s unwavering determination, to the classrooms and corridors of schools that shaped me, I come from good stock, and I carry their lessons with pride.
Thanks, so before we move on maybe you can share a bit more about yourself?
I am an educator at heart.
After over 24 years of leading in education across three continents and four countries, I have decided to shift my focus and push my passions even further.
How?
At the end of the 2023-2024 academic school year, I moved the goalpost-trading the familiar rhythm of school bells for the quiet power of the written word, new cultural experiences, and the joy of lifelong learning.
Writing has always centered me-yes, it allows me to feel at peace and provides the opportunity to journal, reflect, and give voice to the untold stories within and around me. There is something deeply powerful about transforming everyday experiences into narratives that uplift, heal, and inspire. What’s most exciting is how writing helps me to connect with others in ways that are both personal, purposeful, and transformative.
As an international school advisor with NEASC (New England Association of Schools and Colleges) – the global leader in international school accreditation, this year, I have had the incredible opportunity to serve 4 schools in three countries. Being a NEASC accreditation advisor is one of the most enriching forms of professional development I have ever received. I not only got to travel and immerse myself in different educational landscapes but also walked alongside passionate educators who are shaping the future of learning.
When I began my reinvention journey, many of my dearest colleagues were puzzled. “Writing doesn’t sell,” they warned. “You already have a career most people only dream of, it takes years to reach where you are in your career now.”
I heard their worries, valued their concerns, and I understood their perspectives, but my dream was louder than their doubt.
One year later with a village behind me, I published four articles, checked three more countries off my list, released my first book, “Mastering the Moment: 10 Keys to Classroom Victory” (available on Amazon), featured in two magazines, and spoke at educational conferences.
I am currently working on “The Gold That Could Not Stay,” a deeply personal collection of poems, letters, and notes exploring love, loss, and healing. Most of the contents were read aloud to my dad on his birthdays and Father’s Day, making this project especially close to my heart.
Releasing this November, this poignant exploration offers a raw and honest look into the relationship of a father and daughter. I cannot wait for you to experience it with me.
In my recently published book, I share the following excerpt from one of my unpublished works:
“I am encouraged by our conversations to explore new destinations and cultures. Dad, you have been dubbed the Open-minded Explorer.”
My journey has not been without challenges, there have been moments of doubt, unexpected setbacks, and days when I had to remind myself of my “why.” But like my father, I have chosen to stay open, to explore, to grow, and to step into unfamiliar spaces with faith and fire.
Do you have a dream tucked away, one that you have been too afraid to chase? I encourage you to make one step today.
Start now.
You
Can
Do
This…
Be open to the unknown. Be brave enough to bet on yourself.
You can find me sharing stories, lessons, and encouragement on Instagram, YouTube, @teachlearnspeak.
And if you would like to explore more or connect with me directly, visit my website: teachlearnspeak.carrd.co
There is so much advice out there about all the different skills and qualities folks need to develop in order to succeed in today’s highly competitive environment and often it can feel overwhelming. So, if we had to break it down to just the three that matter most, which three skills or qualities would you focus on?
Looking back, three qualities have stood out as cornerstones in my journey: kindness, a posture of learning, and respect for time. These values were not just professional tools; they shaped who I became and how I walked through the world.
It was the late great Dr Maya Angelou who once said, “People will forget what you said, people will forget what you did, but they will never forget how you made them feel.”
Kindness has been my compass. I have had my students from as far back as 2 decades ago search across continents to find and share their gratitude, not only for their grades or the engaging lessons that mark my teaching career, but for the way I made them feel seen, valued, and respected. That I believe is the power of genuine care.
I didn’t learn kindness from a textbook, no, I watched it in action through my father’s and grandfather’s words and actions. My dad epitomized quiet generosity. Whether it was leaving the best bananas, plantains, and yams at our front gate for neighbors, accompanying Dahlia and me to community projects, or paying school fees for a struggling family, he taught me that kindness is a legacy, not a gesture. It is a norm, not an exception.
If you are early on your journey to becoming your best self, my advice is to start small. Say thank you. Remember names. Show up for people. The kindness you give today may be the memory that shapes someone else’s tomorrow.
The most effective leaders I know are not the loudest in the room; they are the most teachable. During my time as a teacher and a school leader, I made it a non-negotiable to dedicate one hour each week to learning something new. Whether it was diving into an online course, reading, attending a training, or shadowing a colleague, I made learning a habit. Each term, I would intentionally develop a new skill. What about your goals? What have you done lately to grow and learn?
Many times, my quest to grow would mean staying up much later than normal. However, I kept reminding myself, “This is for me. This is for my growth, do it with zest and vigor Judy-Ann.”
This posture of learning has kept me grounded and growing. It is the reason I could confidently pivot into writing and international education consulting after 24 years, it was not luck, it was preparation.
If this is an area of growth for you, I encourage you to schedule your learning. Make it part of your calendar, not just a wish. Growth is intentional. The more you know, the more adaptable and confident you become.
One of my grandfather’s favorite sayings was, “Time is money.” It wasn’t about chasing wealth, it was about respecting the clock and the commitments we make. Whether it was showing up early to church, meeting deadlines for school reports, or wrapping up meetings with purpose and clarity, I learned that how we manage time says a lot about how we manage trust.
My learning journey has taught me that deadlines are not just about productivity, they create space for closure, reflection, and next steps. It’s also a form of respect: for others’ time, and for your own.
If you are looking to improve in this area, I recommend the use of a planner, set reminders, and practicing finishing what you start. It builds reliability, and that reliability will open doors that your résumé never could…
My journey of becoming has taught me that at the heart of it all, these three values of kindness, learning, and time have not only shaped my professional journey, but have also built lifelong relationships and unexpected opportunities.
If you are in the early stages of your personal development, my advice is to avoid the desire to just focus on climbing the ladder. Focus on how you climb, how you are impacting others success, and who you are becoming along the way. I believe that is what truly leaves a mark.
To close, maybe we can chat about your parents and what they did that was particularly impactful for you?
What is the most impactful thing my parents did for me?
They made me feel nurtured, wanted, and I utterly belonged.
Growing up, I always knew I was loved, not just because my parents said it, but because they showed it. My dad-Joseph Nathaniel Denton, did not just drop me off at the library. No, no! Dad walked beside me, talked with me, and helped me to choose books when we visited the library. He didn’t just check my homework, yes, he sat with me, patiently guided me, and asked questions that made me think deeply. We had real conversations about real things, and through them, I felt seen, heard, and valued.
Dad went to sleep during the height of the COVID-19 pandemic, when the pain of this loss imprisoned me, I reflect on the way he took the time to pour into me and my siblings. I remember him looking at me and saying, “You are the greatest. You will do great things.” Those words still echo in my mind today. Dad’s affirmation still guides me.
That same sense of belonging was also nurtured by my mother and my grandfather. Mom and I always conversed about matters of the heart, and we still talk for hours. My granddad took me under his wings, made me feel special, and helped me to believe that I mattered. These everyday actions were not grand or expensive, but they were consistent, meaningful, and full of presence.
According to Abraham Maslow’s Hierarchy of Needs, belonging is the third tier, just after our physical needs and our need for safety and security. It means that once we are fed and safe, what we crave next is connection. Belonging directly impacts our productivity, well-being, confidence, and overall happiness. Without it, we feel invisible. With it, we thrive.
My learning journey has taught me that Love is spelled T-I-M-E.
The most lasting gift you can give your child is not money, titles, or technology. It’s your time, your presence, your attention. Walk with them. Talk with them. Help them with their homework, listen to their ideas, ask questions, and show up for their dreams.
In a world full of noise, be the constant.
Why?
Because when a child feels they belong, they believe they can become.
Contact Info:
- Website: https://Teachlearnspeak.carrd.co
- Instagram: https://www.instagram.com/teachlearnspeak?igsh=cWM4OWsxNDhzdjV2
- Linkedin: https://linkedin.com/in/judy-ann-g-4544321a0
- Youtube: https://youtube.com/@TeachLearnSpeak
- Other: For contact and inquiries, please email my Assistant at Vanessa.teachlearnspeak@gmail.com
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