The Journey from Self-Doubt to Self-Confidence: Crossing the Chasm

jilliankulakowski
May 1
4 min read

From Self-Doubt to Self-Confidence

A deeply personal reflection on the journey of self-development and the inner work it takes to build lasting confidence.

📝 Sneak Peek the Article

"There was a season where I felt like I was constantly trying to prove myself. I’d rewrite emails ten times before hitting send. I over-prepared, over-apologized, and over-accommodated, hoping it would make me “seen”. And when I was overlooked, interrupted, or minimized, I assumed the problem was me."

Confidence isn’t something you wake up with one day. It’s not a single moment, a title earned, or a compliment received. It’s a journey and often nonlinear, frequently messy, and always deeply personal.

For many of us, the path from self-doubt to self-confidence feels like crossing a vast and daunting chasm. On one side: hesitation, fear of failure, imposter syndrome, and the constant internal questioning of, “Do I really belong here?” On the other side: clarity, courage, and a quiet, grounded strength that says, “I’ve earned my seat, and I trust myself to grow into whatever comes next.”

So, how do we get from one side to the other?

The Stages of Confidence-Building

Like any journey worth taking, the transition from doubt to self-trust happens in stages. Here’s how I’ve lived it and how I’ve witnessed others cross their own chasms.

1) Self-Doubt

It begins with whispers.

“What if I’m not good enough?”

“What if they find out I don’t really know what I’m doing?”

This is where imposter syndrome sets up camp, feeding on comparison, perfectionism, and past failures. It’s a place where many of us linger far too long, shrinking our voice, our ideas, and our sense of what’s possible.

2) Tiny Risks

Then comes a shift, often small and fragile. Maybe it’s the encouragement of a mentor. Or the sting of regret when staying silent felt worse than speaking up.

We take a chance: we share an idea, raise a hand, say “yes” to something that scares us a little.

It’s uncomfortable, but something powerful happens—we realize we didn’t fall apart.

3) Small Wins

One moment of courage becomes the seed for another.

A presentation that goes well. A tough conversation handled with grace. A project we doubted ourselves on, finished and delivered.

Confidence is cumulative. We don’t build it by avoiding challenge—we build it by walking through it.

4) Shift in Inner Dialogue

Eventually, our self-talk begins to change.

“I’m not sure I can do this” becomes, “I’ve done something like this before—I can figure it out.”

The inner critic is still there—but now, it’s no longer steering the wheel.

5) Self-Confidence

True confidence isn’t loud. It’s not the most polished speaker in the room or the person with the flashiest resume.

It’s the steady, earned self-trust that grows when we stop seeking permission and start honoring our progress.

🧭 My Personal Chasm-Crossing

For me, the turning point wasn’t a promotion or a speech. It was learning to trust the value of my work and leadership, even when others couldn’t or wouldn’t see it.

There was a season where I felt like I was constantly trying to prove myself. I’d rewrite emails ten times before hitting send. I over-prepared, over-apologized, and over-accommodated, hoping it would make me “seen”. And when I was overlooked, interrupted, or minimized, I assumed the problem was me.

One of the greatest gifts I received came, ironically, from a series of poor leadership experiences. I saw exactly the kind of leader I would never become. But I couldn’t fully appreciate the weight of that lesson until I tuned out the external noise and started believing in myself.

Confidence didn’t come overnight. It came from leaning into hard feedback, documenting small wins, and building a new inner script:

“You don’t need to be loud to be powerful. You don’t need to be perfect to lead.”

💡 Practical Tools for the Journey

Here are a few things that helped me—and may help you or someone you’re mentoring:

Track Your Wins: Write down moments you’re proud of. Review them on the days when your inner critic is loud.
Talk Back to the Critic: Replace “I can’t” with “I’m still learning.” Growth is confidence in motion.
Find Your Champions: Surround yourself with people who see your potential and reflect it back to you when you forget. Check this out, a personal favorite → Carla Harris TED Talk
Celebrate the Process: Don’t wait for the finish line. Honor the hard steps you took just to get in the race.

🔄 Leading Others Across the Chasm

If you're a leader, coach, or mentor, your belief in someone else might be the bridge they need.

Call out their courage when they can’t see it. Invite them to stretch before they feel “ready.” Remind them: confidence is not a personality trait—it’s a skill they are already building.