The Confidence Crisis: A Real Talk About Entrepreneurship

Where does confidence go—and how do you get it back?

If you’ve ever found yourself riding the entrepreneurial roller coaster, this question probably hits home. Devin Reed, a respected voice in the world of business strategy and storytelling, recently shared a powerful reflection in his weekly newsletter. It was raw, real, and deeply resonant with what so many business owners, leaders, and creatives experience behind the scenes.

Devin admits, “I spiral once a month.”

That’s not something you expect from someone who consistently shares wins and wisdom with a growing audience. But it’s the truth most entrepreneurs live with—no matter how much success you’ve built, self-doubt still finds its way in.

It whispers:

“Am I doing enough?”

“Is this even working?”

“What’s the point of all this?”

And when that spiral begins, creativity shuts down. You stop thinking big. You start just trying to make it through the day.

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The Real Root of the Spiral

Devin makes a critical observation, “I lose confidence when I lose clarity.”

That line right there deserves to be underlined, highlighted, and written on a Post-it note above every entrepreneur’s desk.

It happens in two major ways:

1. You’re deep in the unknown. You’re building something new without a clear roadmap, and uncertainty takes over.

2. You’re stuck in the weeds. You lose sight of the bigger picture because you’re buried in the details.

When these collide, even the smallest tasks start to feel overwhelming.

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The Way Out? A Simple, Honest Plan

After years of going through this cycle himself, Devin landed on a solution. Not a motivational quote or a productivity hack—but a grounded framework that brings confidence back when it fades.

Here it is:

Conviction – Believe in your plan. Even if it’s not perfect. Even if it might fail. You’ll either succeed or learn something better.

Commitment – Go all in. No half-stepping. Confidence grows when you move with intention.

Flexibility – Be ready to adapt. A changing plan isn’t a sign of failure. It’s a sign you’re listening and evolving.

As Devin said, “Confidence isn't the absence of fear. It’s the result of having a plan—even when you're unsure.”

At AYM High Consultants, we meet countless entrepreneurs and business owners who find themselves in this exact place. They’re not broken. They’re not lazy. They’re just lost in the fog of doing it all.

The antidote is clarity. And the best way to get clarity is to pause, step back, and build a new plan. One rooted in purpose. One that aligns with your values. One that gives you the direction to move forward.

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You’re Not Alone

Whether you're running a brick-and-mortar business, scaling a side hustle, or leading a team—know that the spiral is normal. What matters most is how you respond.

At AYM High, we help entrepreneurs not just build better businesses, but reconnect with the vision and values that sparked their journey in the first place.

Confidence isn’t magic. It’s a muscle. And it gets stronger every time you take intentional action—even when you're scared.

So if you’re in the spiral, you’re not broken. You’re just due for a reset.

Let’s build your plan—together.

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Fahim Mojawalla is the Motivation and Mission Lead at AYM High Consultants. He loves what he does and would love to show you how to make 21st century sales and marketing easy, simply by being authentic, appreciative, respectful, responsive, empathetic, collaborative, and all-around awesome. Along with his wife Seema, he is an effervescent co-owner of Island Ship Center, the Spa of Shipping. #FahimFix