My Least Proudest Moment

There are people who knew me early in my career who wouldn’t recognize the leader I am today. They would laugh at the notion that I am now in leadership coaching, with a leadership blog. The kind of intense laugher that makes your face hurt.

Honestly, I don’t blame them.

I made mistake after mistake as their leader, because I wasn’t their "leader." I was the boss.  I cringe for that scared girl at the head of the boardroom table. I even once said the dreaded, "my way or the highway." I could recount hundreds of  examples of what not to do, all from my two years in that position.

What very few people knew at the time was that I was also dealing with something much deeper.

Back then, I wore a mask, one I hoped was thick enough to hide how insecure I really felt. I was promoted too soon, too young, and the imposter syndrome was loud. I smiled through it, performed through it, led through it. But I was terrified to let people see the real me underneath the title. Behind the record breaking results was a performance I had mastered all too well.

I was the youngest director in company history. Instead of feeling pride, I was walking a tightrope, hoping no one would notice how shaky I was. I was afraid they would see me fall, and even more afraid that they would celebrate when I did.

The tension, lack of trust, and deceit spawned into an increasingly toxic environment. I used to blame the team for their actions, never considering that my own leadership had played a role in what unfolded. Eventually, the situation escalated beyond anything I could have imagined. I was assaulted. (Later, I learned that this individual had missed the open enrollment window and didn’t have access to the medication or therapy she needed. That context doesn’t justify what happened, but it does add a layer of complexity I hadn’t seen in the moment. I still think about that day often, how it unfolded, what led to it, how I responded, and whether things might have been different if I had paused long enough to ask if she was okay.)

I didn’t call the police. I didn’t even tell human resources. I believed I deserved that punch. I took a few days off to let my face heal, then put the mask back on and walked in with my head held high, to prove I couldn’t be taken down.

After that, the panic attacks began. They hit hardest when I knew I’d be alone with my team. One day after a meeting, I stepped into the elevator and they followed. I felt the air disappear. I couldn’t breathe. My chest tightened. I grabbed the wall. Then I collapsed. I was told I had blacked out. The medic asked if I had eaten that day. I said I just had coffee. That was easier than the truth.

Every one-on-one, every meeting behind closed doors, every moment of solitude in that leadership role became a battle between my responsibility and my fear. I didn’t know how to say it out loud then, so I just kept going. I didn’t have the support or leadership I needed to work through it. Eventually, I couldn’t keep going at all.

I started therapy. Slowly, I began to name the things that had shaped me: the trauma, the fear, the pressure to hold it all together. And from there, I started building a new foundation.

A few months later, my personal life required I take a unexpected step back. In that space I began doing the work I’d never made time for before.  The work on myself.

I read leadership books, journaled, reflected, and wrote letters I never sent to people I had wronged or disappointed. And maybe most importantly, I learned to say two things I had once been afraid of.

“I made mistakes.”

and

“I forgive myself.”

When I stepped into my next leadership role, I did it with something I hadn’t had before: gratitude. Not just for the opportunity, but for the trust that came with it, and for a chance to lead differently.

I knew I couldn’t just "wing it" anymore. First, I wrote a leadership statement. A clear, honest vision of the kind of leader I wanted to be, and the responsibility I had to show up with purpose if I was going to lead people again. And that vision? It wasn’t about crushing goals or earning titles. It was about people. It was about what I owed them as their leader, not what they owed me because I was the "boss."

Second, I made a commitment to invest in the people on my team. Not just for the benefit of a company, but because I wanted them to feel seen, supported, and empowered. I wanted them to know they mattered. That they had value beyond their performance metrics. That they could grow, fall, get back up, and still be worthy.

That’s when I started leading as myself. Not the scared version who tried to be who she thought she had to be for everyone else. Not the broken version who believed she wasn’t enough. But the version who had walked through it and had something real to offer because of it.

Here’s the truth:

There are people out there who were on teams I led in the past who would probably laugh at the idea of me writing a leadership blog.

I was the worst leader they ever had.

Believe them.

And there are others, people I led after I did the work, who would say the opposite. Believe them, too.

Because leadership isn’t a fixed identity. It’s something you grow into, fall short of, rediscover, and keep refining, over and over again.

So no, I’m not writing this blog because I’ve always gotten it right.

I’m writing it because I’ve gotten it wrong and I chose to grow anyway.

Chris’s Comments:

When I read this, I had to sit with it for a while. Not just because it was powerful, but because it was familiar. The version of myself I was at the beginning of my leadership journey... I wouldn’t want to work for that guy either. I didn’t know how to lead people, so I tried to manage them. I confused control with influence. I confused being loud with being strong. And like Natalie, I wore the mask too. Mine just came with a few extra layers of ego and denial. But underneath? The same fear. The same tightrope. The same collapse that eventually came for me, too.

This post reminds me why we started The Damaged Leader in the first place. Not to celebrate our wins, but to hold space for the wreckage we had to walk through to become leaders worth following. To encourage other leaders to continue their growth. Natalie’s courage to share this doesn’t just speak to the pain, it speaks to the possibility. That the worst version of ourselves doesn’t have to be the final one. That the punch, the panic, the shame, the silence… none of it gets the last word unless we stop growing.

What version of yourself are you still trying to outrun, and what might change if you chose to face them instead?