Meet Gregory Carpenter

We caught up with the brilliant and insightful Gregory Carpenter a few weeks ago and have shared our conversation below.

Gregory, so glad you were able to set aside some time for us today. We’ve always admired not just your journey and success, but also the seemingly high levels of self-discipline that you seem to have mastered and so maybe we can start by chatting about how you developed it or where it comes from?

Ironically, it started with failure, a long, consistent streak of it.
For most of my early life, I was almost good enough. I was a middle-of-the-pack football player and a decent wrestler; my high school GPA hovered around 2.727. I came in second in track and field more times than I can count—always a breath behind. In sixth grade, I ran the spotlight for our school play because I couldn’t bear to be on stage. I played the violin well, but never stood out. I taught myself piano and could play memorized songs, but I never learned theory.
When I got to junior high, there was no orchestra, so I picked up the oboe—because the music teacher said he needed one. I played it, and later the English horn, simply because those were the instruments required in the pit orchestra for high school plays. I had one good solo performance. Every other time, I failed.
In baseball, I shined for a while—two home runs in one game, another that helped clinch a championship. But after Little League, I faded. High school and beyond brought more struggle. I quietly began to believe the story I told myself: I was a failure.
I barely passed high school calculus. Math felt like a locked door, and I didn’t have the key. I figured I wasn’t wired for it, and for a long time, that belief stuck.
But I wasn’t driven by ambition or a hunger to win. It was more basic than that—I just didn’t want to be hassled. I did enough to stay out of trouble, but never enough to stand out. I lived under the radar.
Now I understand that my lack of discipline wasn’t laziness—it was a trauma response. I lived with persistent shyness, fear, and undiagnosed attention issues. I wasn’t unmotivated. I was overwhelmed. My mind, wired for divergent thinking, didn’t fit into the rigid systems around me. So I coasted—detached from a world that didn’t understand me, and one I hadn’t yet figured out how to engage with.
After high school, I joined the Army. True to form, I chose the infantry, assuming it would be the least mentally demanding. But I quickly noticed something: I could see patterns others missed. I identified inefficiencies, contradictions, and more effective ways of doing things. That insight brought frustration. And that frustration became a turning point.
I realized I had two options: keep resenting the system, or outwork it, outthink it, and out-discipline it.
So, I started doing the hard, often invisible work: showing up early, holding myself accountable, asking for feedback I didn’t want to hear, and setting standards whether anyone was watching or not. Slowly, I built a different version of myself.
It started with little things, like folding my clothes and making my bed. Yes, I was in the Army and had to do all that, but I eventually improved to do it better than anyone else. And I learned to clean. Really clean. If there’s one thing Army sergeants care about, it’s spotless floors and bathrooms—and I became the best. I even became the unit barber, cutting everyone’s hair before deployment.
Although my fear of failure still gripped me, I eventually began to excel. I rose through the ranks. And I started taking academics seriously:
• Associate’s Degree – 3.78 GPA
• Bachelor’s Degree – 4.0 GPA, Distinguished Graduate
• Master’s Degree – 3.87 GPA
• Doctorate – 3.67 GPA
In military schools, I also excelled—becoming the Distinguished Honor Graduate, an Honor Graduate, and earning Commandant’s List honors twice.
But perhaps most ironic of all: I went from barely scraping through high school calculus to becoming an adjunct professor of statistics at a graduate school for six years. The subject I once feared became a language I could speak—and teach. Not because it ever became easy, but because I learned how to push through the discomfort, how to break it down, and how to teach others to do the same.
More important than the grades or titles was the shift in how I saw my mind. The same attention issues that once held me back turned out to be strengths—neurodivergent traits that gave me curiosity, creativity, and adaptability. I stopped trying to “fix” how I thought and started learning how to channel it. I became a force in effectiveness and efficiency.
That shift unlocked everything. I became, in many ways, a renaissance man:
• I’ve written a full symphony and performed in a professional orchestra
• Coauthored a book, written poems, short stories, and magazine articles, and spoken at national and international conferences, with audiences up to 5,000 people
• Led training workshops and developed skills across languages, literature, intelligence, music, and technology
• Hosted a radio show for five years, producing over 100 episodes of thoughtful, deeply researched dialogue
• Currently, I am working on a theory for Cognitive Integrity
None of this came from natural brilliance. It came from being average, overlooked, and underestimated—even by myself—and finally deciding not to stay that way. It came from failing enough to overcome the fear of failure, from being frustrated enough to act.

So, where does my self-discipline come from?
It comes from failure.
From fear.
From frustration.
From learning that my greatest liabilities were actually my greatest strengths, once I gave them structure.

Failure is my teacher.
Disorientation became my guide.
Frustration was the forge.
Discipline became the way forward.
Darkness was now my light.

Thanks for sharing that. So, before we get any further into our conversation, can you tell our readers a bit about yourself and what you’re working on?

I work at the intersection of strategy, security, education, and the arts. After 27 years in military service, where I specialized in intelligence and operations, I transitioned into executive leadership in the private sector, while continuing to teach, write, compose music, and speak publicly. What excites me most is the challenge of making complex systems not just functional, but human. I help individuals and organizations operate more effectively, whether through risk analysis, leadership development, or communication strategy. My work isn’t built around hype or flash, it’s grounded in discipline, adaptability, and creative thinking born from adversity. I started off as a quiet, average kid who could barely pass high school calculus. Years later, I was teaching statistics at the graduate level and creating original symphonic works, as well as articles and books. That’s the throughline of my story: taking what seemed like limitations and turning them into leverage. Right now, I’m focused on developing new content that supports neurodivergent professionals and unconventional thinkers—people who, like me, were never quite wired for the traditional path but still have a lot to offer. I believe the world needs more minds that don’t fit in—because those are the minds that move us forward.

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, the three most impactful elements in my journey were resilience, pattern recognition, and self-discipline.

Resilience was foundational because I failed often and early in my life. I wasn’t naturally gifted or confident, but I eventually learned to get up every time I stumbled. For anyone starting out: don’t avoid failure. Learn to analyze it, own it, and move forward. That’s where real growth happens.

Pattern recognition allowed me to thrive in complex environments—from military operations to academic systems. Developing this skill means being observant, asking “why” often, and learning to connect seemingly unrelated dots. Read widely. Stay curious. Never assume the obvious answer is the only one.

Self-discipline was the bridge between potential and reality. It didn’t come naturally—it was built slowly, through small, consistent actions that nobody else saw. Start there. Build routines that reflect your values, not your mood. The work you do when no one’s watching is the most formative.

If you’re early in your journey, lean into discomfort. Focus more on direction than speed. And above all, don’t wait to be ready—start where you are and build from there.

Awesome, really appreciate you opening up with us today and before we close maybe you can share a book recommendation with us. Has there been a book that’s been impactful in your growth and development?

Two books had an equally big impact on me: Notes to Myself by Hugh Prather and Flatland by Edwin Abbott.

Notes to Myself felt like reading someone else’s private journal and realizing it could’ve been mine. It taught me the power of being honest with yourself, not polished or performative, just real. That kind of self-awareness significantly shaped my growth.

Flatland flipped my thinking. It made me question assumptions and see how limited our perspective can be if we never step outside our own dimension, literally and metaphorically. It taught me to look deeper in ways I never thought possible. It taught me to look for the unseen as part of my naturally accepted perspective of my existence.

Contact Info:

• Linkedin: https://www.linkedin.com/in/gcarpenter-cso-kbi/
• Other: https://sessionize.com/gregory-carpenter/

Image Credits

I own all images