You know, I want to start with something I see all the time with nonprofit CEOs and executive directors—and if I’m honest, something I’ve experienced myself.

It’s that moment where you’re in a leadership role, you’ve worked hard to get there, you care deeply about the mission… and yet there’s this quiet question running in the background:

Am I the right person for this job?

You make decisions, and then you revisit them.
You say something in a meeting, and then you replay it later.
You wonder if you moved too fast… or not fast enough… or handled something the wrong way.

And what’s tricky is that from the outside, everything might look completely fine. Your team sees you as capable. Your board trusts you. But internally, there’s this layer of second-guessing that just keeps showing up.

So today, I want to talk about what it means to lead with confidence and conviction—and more importantly, where that confidence really comes from.

A few years ago, I came across a framework from Dan Sullivan, an entrepreneurial coach, and it stuck with me in a way that most leadership frameworks don’t.

He talks about the 4 Cs of confidence. And they build on each other in a very specific order:

  1. Commitment.
  2. Courage.
  3. Capabilities.
  4. Confidence.

And when I heard that, I thought, this is exactly what I see in strong leaders. But I also realized something was missing for nonprofit leaders specifically.

So I want to add a fifth C to this. And that’s certainty.

Because confidence is powerful… but certainty is what allows you to hold your ground when things get uncomfortable.

Let me give you an example from my own life that I still think about today.

I grew up in Anaheim, California, and swimming was just something we did for fun in the summer. Nothing serious.

In middle school, I joined a rec center swim team—again, pretty casual.

But then freshman year of high school, I decided to join the actual school swim team. And let me just paint the practice picture for you.

We need to show up at the pool at 6am daily. It’s an outdoor pool.
It’s still dark outside. The air is cold in the mornings there – maybe 40s or 50s outside.
And you’re standing there in a speedo, which, let’s be honest, is not exactly a confidence booster at 14 years old.

I walked into that environment with very little confidence. But here’s what happened.

First, I committed. I showed up every day. Early mornings, cold pool, lap after lap.

Then came courage. Because I had to be willing to be bad at it. To be seen learning. To not know what I was doing and still get in the water anyway.

Then, over time, I started building capabilities. Learning each stroke—freestyle, backstroke, breaststroke, butterfly. 

Working on flip turns. Building endurance. Understanding how to pace myself.

And after months of that… I had built just enough confidence to hold my own in races.

Not to be the best. Not even close. But enough to keep going.

Now here’s where it gets interesting. At the end of the season, during our last swim meet, the varsity team needed someone to fill in for the 500-meter freestyle.

That’s 20 laps.

And I’m a freshman. Competing against seniors. The coach comes up to me and asks if I’ll do it.

And my immediate reaction was: Absolutely not.

I’m not good enough.
I’m going to embarrass myself.
This is a terrible idea.

All the self-doubt showed up instantly. But after all the excuses ran through my brain, I don’t what happened but something shifted.

Not because I suddenly felt confident. But because I had already:

I swam more than 20 laps/day in the dark, in the cold, at 6am. Why shouldn’t I try to race with the varsity team? 

So even though I didn’t feel ready and felt totally unsure… I said yes.

Now, quick side note—before this race, our team had what we called a “shaving party.”

Which sounds ridiculous, and honestly, it was. But it was a real thing.

By the side of the pool, the whole team has a tradition – we would gather together with bottles of shaving cream and razors and literally shave our arms, legs, backs—everything—because any hair creates drag in the water.

So there we are, a bunch of teenagers, by the pool, shaving each other’s backs, preparing for this big race.

And then the moment comes. Final race of the meet. Everyone’s in the stands—parents, teammates, friends.

I’m standing on the block next to seven senior swimmers.

Heart racing. Second-guessing everything.

Why did I say yes to this?

3-2-1- The buzzer goes off. We dive in.

And I just focus on one thing, stroke by stroke.

Lap after lap. Flip turns. Breathing. Endurance.

Did I win? Not even close. But I finished at a respectable time.

And what I didn’t expect was immense pride in myself. 

I didn’t embarrass my team. I held my own. And most importantly, I became someone who says yes to things that feel scary than me.

And that’s the point I want to bring back to you.

Confidence didn’t come first. It came after commitment, courage, and capability. 

And what that experience built in me—looking back—was certainty. Not certainty that I’d win. But certainty that I could handle something before I felt the elusive “ready”.

So let me ask you this. Where in your life have you already done that?

Where have you said yes to something that stretched you?
Where have you figured things out as you went?
Where have you grown into a role that you weren’t fully ready for at the time?

Because if you’re leading a nonprofit organization right now…

You already have a track record of doing hard things.

So here’s your bold move coming out of this episode.

I want you to set aside a quiet, uninterrupted 30 minutes this weekend to create a Win List. Not a resume. Not a list of responsibilities.

A list of moments where you showed:

Times where you stepped into something uncertain and came out stronger. Because confidence grows when you build certainty.

And certainty comes from evidence. Your own lived experience.

So if you’ve been second-guessing yourself lately, I want you to remember this:

You don’t need more confidence first. That’s too elusive sometimes. You want to reconnect with the path that creates it.

Commitment.
Courage.
Capabilities.
Confidence.

And then—certainty.

If you found this helpful, you’ll love being part of my newsletter community of mission-driven leaders. You’ll get practical leadership insights relevant to growing your nonprofit, early access to new episodes, and a few resources I only share there.

You can head to CultureCARES.com and download the free guide:

4 Strategies for Nonprofit Leaders to Reduce Burnout, Unify Your Team, and Build a Culture That Lasts.

And in this series, we’re going to keep building on this. I’ll be sharing specific tools, mindset shifts, and real nonprofit leadership situations that you can apply right away.

My goal is that by the end of this series, you’re not just leading with more confidence, but with real certainty in how you show up as a leader.

TOPIC: Design an Inclusive Culture, Lead with Confidence, Podcast, Unify Your Teams