We recently connected with Baron Stewart and have shared our conversation below.

Baron, looking forward to hearing all of your stories today. Going back to the beginning – how did you come up with the idea in the first place?

Why I’m Writing This Book and providing service to speak to groups and organizations

Before I ever thought about writing a book, leading a seminar, or standing in a boardroom, I sang.

As a child in Jamaica, I was known for my voice. At Calabar Elementary School, I was the best singer—the voice of the Christmas carols. Later, I became the only boy in a girls’ choir that performed at Kingston’s Ward Theater. Singing wasn’t just something I did—it was who I was. My earliest sense of self-worth came from that voice.

Then came Kingston College. I was thirteen, auditioning for the school’s distinguished choir. The choirmaster loved my voice so much he’d ask me to stay after and sing for him privately. I was filled with hope—this was my moment.

But on the day of the final audition, something unexpected happened. I was singing “Oh Come All Ye Faithful” when my voice cracked. It broke. And just like that, I didn’t make the choir.

I was crushed. I never sang again.

Looking back, that moment left more than just silence. It left a longing—a need to be heard and give voice to something real inside me. That longing never left; it just changed form.

I once wanted to be a minister, not for religion, but for the pulpit. Later, I became a professor. Then, I was a seminar director. Then, I was an executive instructor. I was a speaker. Every role pointed to the same truth: I am here to speak.

And now, after raising three incredible children—Madison, Justin, and Jo—with my wife, Berkeley, after years of holding back my dream for my family’s stability, I’m finally writing the book that will allow me to do just that.

To speak.

But this book isn’t only about me. It’s about you. It’s about helping you recognize the moments in your life, especially those that broke you open, and learning how to listen to them. To find your voice, however it wants to come through.

Because sometimes, when we can’t sing anymore, we speak.

As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your back background and context?

I am Baron Appleby Stewart, a Jamaican-born educator, writer, and speaker. I have shared reflections on my experiences in the United States, including my time working at IBM. In my article “Beyond Chicken Bones,” I recount how my Jamaican cultural background influenced my professional life in America. I mention that my relaxed demeanor, often perceived as a lack of commitment, affected his career progression at IBM. Specifically, he notes missing out on a Seminar Director position because he “did not look the part,” highlighting my challenges in adapting to corporate expectations while maintaining my cultural identity. ​

My passion for dance is evident in my keynote speech, Business Dance, which I delivered across the United States at conferences and business meetings. My latest work is Hindsight—100 life lessons from a Jamaican flower, in which I discuss the journey of a poor Jamaican immigrant who moved from an elevator operator in 1970 to IBM Executive Instructor and Facilitator of mathematics at the University of Phoenix.

Is there a particular goal or mission driving your creative journey?

Questions That Have Guided My Life—and May Guide Yours
These are the questions I’ve wrestled with, lived through, and now offer to you, not as finished answers, but as reflections shaped by experience:

Identity & Purpose
How do I figure out who I am beyond the roles I’ve played?
There has always been a yearning in me to perform. That desire, not the titles I’ve held, reveals who I am at my core.

What if I feel like I missed my calling—can I still fulfill it later in life?
Absolutely. Dreams evolve, but their essence stays alive. They may look different on the outside than you expected, but they’ll still light you up from the inside. Sometimes your children live out your dreams, and you feel the joy through them.

How do I find meaning in the story I’ve lived so far?
For me, meaning comes when I see emotion in my listeners’ eyes. That connection tells me my story is landing where it’s needed.

Voice & Expression
What does “find my voice” mean, and how do I do that?
It means discovering what you’re good at and making it stronger. Speaking does that for me—it engages both my analytical and creative sides. I call this Whole-Brain Education.

How can I share my truth without fear or shame?
I don’t carry much shame. I take some regret. But I’ve learned to speak openly about what others might hide, because I believe vulnerability is where the magic lives.

What do I do when something I loved (or was good at) is no longer available to me?
I found something else. I’m good at math and teach it, but speaking fills me up ten times more. Speaking uses both my logic and my heart.

Transformation & Resilience
How do I move forward after a major disappointment?
Disappointment is a breakdown, and breakdowns are the doorway to breakthroughs.

Can I turn my pain into power?
I’m doing that now, through this book and the speaking that will follow.

What’s the process of turning life experience into life wisdom?
It’s the journey from hindsight to insight. You look back to learn how to move forward better.

Family & Responsibility
How do I balance personal dreams with family responsibilities?
That’s been my greatest challenge. Success in one area can mean sacrifice in another. There’s always a yin and a yang. We must choose—and accept the consequences.

What happens when the needs of others delay or reshape my goals?
It’s not a delay—it’s an unintended consequence of choice. Every choice has its ripple effects.

Can I still honor my dream while being a present parent or partner?
Yes. But it’s a matter of degree. You lean into one and adjust the other. There are rewards, and there are trade-offs.

Legacy & Contribution
How do I make peace with the choices I’ve made?
Easily. I forgive myself. I understand that no matter what I’d chosen, I would’ve carried some form of regret. That’s life.

What legacy do I want to leave—and how do I start building it now?
Love. That’s the legacy. And I start building it by telling my truth, living with presence, and speaking to help others wake up to their own story.

How can I help others by telling my story?
By learning from my own. And by helping others learn to listen to their

Have you ever had to pivot?

The Mirror Incident

At Christmas of 1979, I was riding high at IBM. After two years of hard work and recognition, I had become the department’s top contributor. But that Christmas party changed everything.

The programming team gathered for its annual Secret Santa gift exchange. The mood was festive. When your name was called, you walked to the front of the room, accepted your gift, and opened it for everyone.

When my name was called.

I got up, walked to the front, and accepted a flat, neatly wrapped package. The room fell silent as I stood there. I glanced at the sea of white faces watching me, waiting.

I tore off the paper.

Inside was a mirror. Above it, in bold black letters, was a single word:

PROBLEM.

I looked into the glass and saw my reflection beneath the word.

The room erupted in laughter.

I stood there, holding the mirror, the edges digging into my hands. I sat down without saying a word.

Inside, I was furious, humiliated, and rejected. But more than anything, I wondered why I was working so hard in a place that saw me, not my ideas, not my contributions, but me as the problem.

Looking back, I understand now.

I had written about and offered solutions to IBM’s problems, and I had been given funding to fix them. In a short time, I became the department’s most successful programmer.

But I wasn’t one of them anymore.

They also resented that Keith, my implementation partner, hadn’t received the same recognition. He was an artist with excellent visual talents and a master coder, but the organization was rewarding leadership and innovation. I was the one with the ideas, and Keith followed me.

And then there was something else. I hadn’t made the effort to connect with them. I didn’t drink with them on Fridays, have lunch with them, or share stories. I was focused on my work, and it showed.

I had a bright manager who recognized my talents and gave me every opportunity to use my analytical skills. However, I had few people skills, and in the workplace, that mattered more than I understood at the time.

They didn’t just resent my success.

They resented that they didn’t know me.

And I didn’t know them.

The mirror incident forced me to reflect—literally and figuratively. I realized I had been leading with my left brain—logic, analysis, precision. It had served me well technically, but it had left me isolated.

I wanted to develop my right brain. To balance who I was.

The following year, I bought a camera and took it on vacation. I started photographing people, mostly strangers I met along the way. Asking to take someone’s photo led to conversations, and conversations led to friendships. I was learning to connect in ways I never had at work. That simple act softened me. It opened a new possibility for me to relate.

And gradually, I started making friends everywhere.

Even at IBM.

But not long after that Christmas party, I made a decision that changed everything for Keith and me.

John offered me the leadership role on our next significant systems development project. It was high-profile, and I was already the technical leader shaping the design.

But I declined.

I told John to give Keith the project management role.

John was surprised. He asked if I was sure, and I told him I was. Keith should have his moment. If he took the lead, I thought he’d get the recognition he deserved. After some thought, John agreed.

Keith succeeded as project manager. The following year, he received a leadership award that I had won.

I didn’t receive one.

My relationship with John never wavered, but Keith changed. We had once worked as partners. Now, he was competitive, less of a collaborator, and more of a rival.

Soon after, the department promoted me to the Technical Staff. It was a significant step forward. I was no longer responsible for programming or project implementation. Keith took over all of that.

My new job was to analyze and restructure IBM Software Distribution in preparation for its move to the brand-new, state-of-the-art facility in Sterling Forest.

It was a vast project—an exciting opportunity. The scope was more extensive than anything I’d done before.

But I knew something had shifted.

My responsibilities had changed. My relationships had changed. I had changed.

I wasn’t just an analyst anymore.

I was on a journey to become something else.

But that’s a story for another time.

Image Credits

Baron Stewart