The Confidence Gap: Why Confidence Might Be the Most Essential Skill Leaders Never Get Taught

In my last piece, I talked about the most expensive problem in business — the misalignment between self-worth and decision-making. It’s the invisible tax entrepreneurs pay when doubt, hesitation, or guilt creep into their leadership.

But where does that misalignment come from? Why do smart, capable people, people who’ve built incredible things, still hesitate to take the next step?

That’s where the real problem lives. Not in the strategy. Not in the systems. But in what I call the confidence gap - the space between knowing the right move and actually making it.

My Experience with the Gap

In my life, confidence was never something my parents, teachers, or even coaches really taught me. They might have told me to “be confident,” but no one ever explained how to build confidence. The only guidance was the old cliché: fake it till you make it.

On the flip side, growing up, we were ridiculed, shamed, or “put in our place” if we came across as too confident - or worse, arrogant.

I remember one moment clearly. It was the early 1970s, and my uncle - an entrepreneur who grew up in very humble beginnings during the Depression, pulled up to our house in a brand-new Cadillac. He wore a sharp suit, my aunt wore a new dress and a mink coat. He hadn’t finished school, but he was smart and resourceful, and he wanted to show my mom, his childhood best friend, that he had made it.

Instead of celebrating his success, my mom looked disgusted. I know that look; I saw it often. To her, he wasn’t successful, he was arrogant. My mom lived by the philosophy: “Be humble, or God will make you humble.” Later, when my brother told her my uncle had gone bankrupt, she almost seemed satisfied, as if she had been proven right.

That moment stuck with me. Looking back, it often felt like the mission of those around me was not to build confidence but to strip it away.

• As kids, we’re shamed for mistakes instead of encouraged to try again. We’re compared to others instead of taught to measure progress against ourselves. We’re told to sit down, be quiet, and not stand out too much. All of it chips away at self-belief.

• As adults, it doesn’t get easier. Workplaces critique performance more than they coach growth. Social media fuels comparison more than truth. Even well-meaning people in our lives sometimes doubt us out loud instead of lending belief.

All of it erodes confidence. And if we’re not careful, we begin to accept that erosion as normal.

In my career, I’ve gone back and forth between learning and doing. I’d set a big dream, get fired up, and dive headfirst into every best-selling book, every popular course, every strategy framework. I obsessed over building the perfect plan.

But then that old familiar voice would creep in during a moment of hesitation, doubt, anxiety, and fear. “Who do you think you are?” “What makes you think you could ever do this?” “People are going to laugh at you when you put yourself out there, and you’ll destroy your reputation when you fail.” And immediately I’d start second-guessing myself - my ability, my value, my worth.

I’d delay the tough conversation. I’d freeze before the bold move. I’d convince myself the timing wasn’t right, or the idea wasn’t solid enough. And suddenly, I was stuck. Not because of knowledge, but because of confidence.

Worse, I’d rationalize it. My head would serve up all kinds of “logical” reasons why backing down was the smarter path. And yet, deep down, I knew the truth: I wasn’t searching for strategy, I was searching for safety, for validation. I wanted someone else to tell me I could do it. But the reality was, no one else could believe in me enough to override my own self-doubt. That’s how strong my inner critic was.

Even when I had the skills. Even when I was already an expert. Even when I had proof to the contrary. The voice still whispered: “You are not enough.”

And here’s the part I still wrestle with

I’ve done the things that were supposed to build confidence. In the Marine Corps, they literally had us run the “Confidence Courses”, a series of grueling physical obstacles designed to push you past your limits so you walked away believing in yourself. And it worked… for a time. I was confident in specific abilities, confident in what I could do in the middle of the mission. But what about after?

It reminds me of that scene from the Documentary part of Band of Brothers when Shifty Powers said he had all the confidence in the world during the war, but once it ended, so much of that confidence disappeared. I get that. I felt it too.

Outside the mission, outside the uniform, outside the context of “prove yourself or fail,” I was left asking: Where did that confidence go?

So what happens to all those traditional things that are supposed to build us up? The medals, the wins, the promotions, the hard courses passed, the doing the hard things. Why do they fade when we step into a new season of life or business?

I don’t have all the answers, but I know this: external achievements can spark confidence, but they don’t sustain it. True, lasting confidence has to be rebuilt again and again from the inside out. And that’s why the confidence gap doesn’t disappear just because you’ve done hard things before, it shows up every time you face something new. And that is ok, and believe it or not, its very common especially among leaders and entrepreneurs.

Where the Gap Will Show Up

If you’re like me, you recognize the pattern. The confidence gap doesn’t just show up in small ways. It touches everything, especially the things we might have never experienced before:

• Business: avoiding price increases, holding back on scaling, not making the sales call.

• Leadership: micromanaging instead of leading, avoiding feedback, indecision in front of the team.

• Career: passing up opportunities, staying “safe” instead of stretching.

• Relationships: silence instead of honesty, tension instead of connection.

• Parenting: reacting in frustration instead of modeling calm confidence for our kids.

Why This Matters

I’ve seen hardworking, good-hearted entrepreneurs with executable ideas stall out, not because they lacked knowledge or resources, but because doubt froze them before they ever took the shot.

I’ve watched leaders who knew exactly how to guide their teams shrink back in meetings, afraid their voice wasn’t enough. The result? Confusion, frustration, and missed opportunities that could have changed everything.

And I’ve lived it myself.

When I owned my restaurants, I avoided looking at online reviews for years. They weren’t just reviews of the food or the service, they felt like reviews of me. Every negative comment cut straight to my worth as a person, not just as an entrepreneur. I’d obsess over what was said, or worse, I’d avoid it altogether because I couldn’t face the judgment.

The reality is, I wasn’t afraid of feedback about the business. I was afraid that the feedback confirmed what that little voice in my head already told me: “You’re not good enough.”

That’s the cost of the confidence gap. It doesn’t just block bold moves, it eats away at your ability to hear truth, to adapt, and to grow. It keeps you from seeing the lessons in the feedback because you’re too busy turning it into a verdict on who you are.

And this is why I believe confidence might be the most essential skill leaders never get taught. You can get an MBA, hire the best consultants, and read every strategy book on the shelf. But if you don’t believe in yourself enough to take the step, and to face the truth when it shows up, none of it matters.

Business is as much a mental game as it is a numbers game, confidence turns knowledge into action, and action into results. But what if confidence isn’t a feeling we stumble into, but a skill that can be taught, practiced, and strengthened like any other?

Three Ways to Start Closing the Gap From the Inside Out

1. Reframe failure:
Yes, we grow from our failures. But the word itself carries such a heavy weight. Failure sounds final, permanent, defining. It can crush our mental state before we’ve even had the chance to recover.

When I call something a Miss, instead of a failure, it changes the energy. A miss is just feedback. It’s an attempt that didn’t land the way I wanted, but it doesn’t define me. A miss gives me permission to learn, adjust, and improve, without the punishment. And it transforms the label from “I am a Failure” to “I just missed it this time and I will get it next time”.

That shift in language alone has saved me from spirals of self-doubt and kept me moving forward.

2. Raise your standards:

When confidence wavers, your standards and systems can hold you steady. Lean on process and structure when self-doubt sneaks in.

Create the standard for yourself that says:

• I will show up and do the work, even when I don’t feel ready.

• I will keep my commitments - to myself and to others - even when my emotions tell me otherwise.

• I will trust the process I’ve built more than the fear I feel in the moment.

When your standards are higher than your self-doubt, structure carries you where confidence can’t. It’s the difference between drifting with your feelings and being anchored by your principles.

3. Expose yourself to action:

Confidence doesn’t come before action, it comes because of it. So take the hard step, get the reps, and let confidence grow from the doing.

We learn so much in the doing. That’s where growth happens, and that’s where confidence begins to take root.

This is also where mentors, advisors, and coaches bring the biggest benefit - not in theory, not in abstract strategy sessions, but in the trenches of the work itself. Yet this is exactly why so many people hesitate to hire the coach they need: it feels safer to be living and working in the realm of ideas than in the grinding reality of execution.

But here’s the truth: a coach is most effective when they’re with you in the hard moments, pushing you through the hesitation, challenging your stories, holding you accountable as you take action.

When you start closing your confidence gap, you stop sabotaging yourself. You stop waiting for permission. You stop hiding behind knowledge.

You become decisive.
Your leadership presence grows.
Your relationships deepen.
And yes, your business grows.

Because skills matter. But skills without confidence is wasted potential.

Final Word

The confidence gap is real. And every day, you either let it widen, or you do the work to close it. Because confidence isn’t just a nice-to-have. It might be the most essential skill leaders never get taught.

That’s what I teach and coach: how to turn self-doubt into decisive action, so you can grow your business without losing your confidence, your relationships, or your peace of mind.

If this resonates, subscribe, share this with someone you know, and let’s start closing the gap together.