The Confidence Myth: Why Most Leaders are Making it Up As They Go

From the Heart: Lessons, Laughs, and Leadership
— The Confidence Myth: Why Most Leaders are Making it Up As They Go (And why that’s not a problem—it’s the point)

Ever looked at someone in a leadership role and thought, "Wow, they really have it all figured out…”?

I’m here to lovingly shatter that illusion.

Because the truth is—most of us are making it up as we go. Not recklessly. Not carelessly. But constantly learning, shifting, evolving, testing, and trusting our instincts, even when the road ahead is foggy and full of potholes. That’s not a flaw in leadership—that is leadership.

Imposter Syndrome: Practically a Job Requirement

Here’s something I wish more people would say out loud: imposter syndrome isn’t just common among leaders—it’s basically a prerequisite.

Especially if you care deeply about what you’re building.

Because when the stakes are high, and the vision is bold, and people are looking to you for decisions, clarity, and calm—you will occasionally question whether you’re up for it.

That doesn’t make you less capable. It makes you aware—and that awareness, when channelled correctly, keeps you thoughtful, curious, and open to growth. In my experience, the leaders who never question themselves? They’re either brand new, or dangerous.

Confidence isn’t Knowing—it’s Moving Anyway

There’s this idea floating around that confident leaders walk into every room with all the answers. I don’t buy it. True confidence is built when you can say, “I don’t know yet—but I’ll figure it out.”

It’s not swagger. It’s not ego. It’s the calm, steady ability to face uncertainty without letting it derail you.

I’ve led product launches I was nervous about.
Pitched ideas that felt half-baked.
Made hiring decisions based on gut instinct.
Launched initiatives without a detailed roadmap.

And you know what? Most of it turned out okay—sometimes even great. Not because I knew it would work, but because I trusted myself to navigate it if it didn’t.

Leading in the Middle of the Mess

We live in a world that rewards certainty. But startups are a breeding ground for ambiguity. You’re building new things in new ways—often with limited resources and more unknowns than answers.

Which means the real leadership skill isn’t pretending you have it all figured out—it’s being willing to lead anyway.

You listen. You learn. You adjust.
You don’t hide your uncertainty—but you don’t let it paralyse you either.

And when your team sees that? They learn it’s okay to not be perfect. It gives them permission to try, fail, and grow. That’s the culture I want to build. One where confidence means courage, not cockiness.

What Confidence Really Looks Like in Leadership

It looks like:

• Asking the “dumb” question in the boardroom, even if you're the most senior person there

• Admitting when you missed the mark, and being willing to course correct

• Showing up on the tough days, and still moving things forward—bit by bit

• Empowering your team to make decisions, even when it's tempting to hold the reins tighter

• Backing yourself, even when the outcome isn’t guaranteed

Confidence isn’t a feeling you arrive at—it’s a practice. It’s built in motion. And often, it’s just quiet consistency over time.

I’ve Been There Too

I’ve had moments where I was sure everyone else had it together and I was the only one feeling wobbly.

But the more I leaned into conversations with other founders, leaders, and mentors, the more I realised the “I’m winging it a little” feeling is everywhere. It doesn’t mean you’re not cut out for this. It means you’re in it. You’re doing the hard, brave work of showing up, even when your inner critic wants you to sit down.

So if you’re leading a team, building a business, or just trying to keep moving while the path is still forming beneath your feet—welcome. You’re not behind. You’re exactly where you need to be.

Let’s Redefine Confidence—Together

You don’t need to be fearless to be a great leader. You don’t need to be flawless. You just need to keep showing up with integrity, curiosity, and the willingness to get better.

The real myth? That leadership is about certainty.
The reality? It’s about the courage to innovate with humility.

So here’s to all of us out here building, trying, stumbling, and figuring it out as we go.

You're not faking it.
You're leading.

At Roamlii, we believe in the kind of leadership that grows with you—built on real momentum, not just posturing. If you’re figuring things out (just like the rest of us), let’s build something great anyway.

👉 #GetRoaming and let’s shape the future—confidently uncertain, and boldly moving forward.

Yours in tourism, innovation and startups,

Founder & CEO
Roamlii