Leading with AI isn’t about mastering the tools — it’s about mastering yourself through every wall you face.
The Fog Before the Climb
I didn’t start my AI journey from a place of excitement. I started from a place of resistance.
Fear. Doubt. Overwhelm. The quiet, reasonable voice whispering “You don’t have time to figure this out right now.” These emotions wrapped around me like a heavy fog, clouding my judgment and anchoring my feet in place. It was easier to stay busy putting out today’s fires than to face the uncertainty of tomorrow.
I remember sitting at my desk one afternoon staring at yet another batch of AI-generated social media posts I’d prompted for. It was… fine. Technically correct. Completely lifeless. I tried again. And again. Wall after wall. What should have been easy felt impossibly complicated.
As my headache set in from a combination of an overheating brain and a forehead repeatedly hitting the desk, it finally hit me: you can’t bottom-up your way into success with AI. No clever prompt would do it. I had to rethink everything from the top down. I stepped back, took a deep breath and a new approach, and finally, I got the results I was after.
The hardest part wasn’t learning the tools. It wasn’t understanding prompts or fine-tuning workflows. The hardest part was, and still is, managing the emotional journey that leadership demands in this new era of AI.
If you’ve felt that fog, if you know you “should” start but can’t seem to move, you’re not broken. You’re just standing at the first wall of the AI Learning Cycle.
The Shift: It’s Not About the Tools. It’s About Who You Become.
Learning AI isn’t just about new skills. It’s about a new identity.
There’s a predictable, and deeply human, journey every leader must travel to turn AI into a strategic advantage. It’s not a simple learning curve. It’s an emotional mountain climb, filled with peaks of excitement, valleys of frustration, and barriers that must be broken through.
I call it the AI Learning Cycle, and it mirrors the journey of leadership growth itself:
- Exploration Stage—Testing the waters, battling fear, flirting with curiosity, confronting frustration.
- Application Stage—Gaining small wins, hitting deeper despair when surface tricks no longer work.
- Transformation Stage—Partnering with AI at a strategic level, expanding your thinking, beginning the next climb from a higher place.
And standing between each stage? A wall:
- Wall of Resistance—The fear that keeps you from starting.
- Comfort Zone Wall—The temptation to settle after early success.
- Identity Shift Wall—The discomfort of becoming someone new.
- Expansion Loop—The humility of starting over again and again.
Each wall is not an obstacle to avoid. It’s a gatekeeper asking, “Are you ready to grow?”
Breaking through these walls isn’t just how you master AI. It’s how you become the leader your future demands.
Here’s what the AI Learning Cycle looks like…a journey marked by peaks of growth, valleys of challenge, and the walls every leader must break through.
My Journey Through the Walls
When I look back now, the journey feels obvious. But when you’re in it? It hurts. It feels like doubt and chaos.
Wall of Resistance: For months, I told myself, “I’ll get to it when I have more time and clarity.” Deep down, I knew that “more time” was never coming. What got me moving wasn’t certainty, it was admitting that waiting was the bigger risk. Leadership is rarely about having perfect timing. It’s about choosing to move even when the path is unclear.
Exploration Stage: I dipped my toes in. The fear that I’d waste my time gave way, little by little, to curiosity. But just as quickly, frustration followed. Why wasn’t this easier? Why did it feel like everyone else “got it” faster? It was humbling to realize: exploration means feeling lost on purpose. You can’t shortcut your way to true understanding.
Comfort Zone Wall: After a few early wins, I felt a rush of excitement. I thought, “I’ve cracked it.” I hadn’t. I had learned just enough to be dangerous…and just enough to stop growing. Comfort disguised itself as competence. The only way through was to admit that “better prompts” weren’t enough; a better mindset was needed.
Application Stage: Deeper despair came next. The hacks and shortcuts that once thrilled me fell apart when I needed real strategic leverage. It was a punch to the gut. But despair, I learned, is just frustration that stayed too long without new perspective.
Identity Shift Wall: This was the real crucible. I realized I wasn’t just learning to “use AI.” I was being asked to become a different kind of leader…one who co-creates, experiments, and stays adaptable. The fear here was real: if I let go of who I was, what would be left? But on the other side of letting go was a leadership style more resilient, more imaginative, more human.
Transformation Stage: Breakthrough moments came not from mastering AI, but from partnering with it. Letting it challenge my thinking, sharpen my ideas, and expand what was possible. And just when I felt like I had “figured it out,” the Expansion Loop appeared, inviting me to begin the climb again, this time with bigger stakes, more dramatic emotional swings but with deeper humility and an upgraded AI Leadership operating system.
Every wall broke me open just enough to let a better version of myself step forward.
And that’s what real leadership looks like now: growing, breaking, and becoming—over and over again.
Where Are You Standing Right Now?
Maybe you’re standing at the Wall of Resistance, hesitating at the starting line.
Maybe you’re inside the Exploration Stage, riding the overwhelming emotional whiplash of curiosity and frustration.
Maybe you’ve hit the Comfort Zone Wall, mistaking early wins for mastery.
Maybe the Identity Shift Wall looms ahead, whispering doubts about what “work” actually is anymore.
Wherever you are—you’re exactly where you’re supposed to be.
The only wrong move is standing still.
Ask yourself:
- What am I feeling right now about AI—and what does that tell me about where I am in the AI Learning Cycle?
- Am I willing to take the next imperfect step forward?
The path isn’t a straight line. It’s a climb, a stumble, a climb again.
And every step, every misstep, every wall faced is shaping the leader you’re becoming.
A Leadership Path Waiting for You
AI isn’t just changing our tools. It’s changing what leadership demands from us.
The first skill isn’t technical. It’s emotional courage.
Not courage to be perfect. Courage to begin. Courage to stay. Courage to keep becoming.
You don’t need to have it all figured out today. But you do need to start the climb.
Because on the other side of each wall isn’t just a better leader, it’s a new kind of leadership; one your future, your team, and your own deeper potential will thank you for.
The path is waiting. The next step is yours.
Lead With Energy (and AI),
Derek