Embracing Authentic Leadership: Navigating Transitions and Owning Our Story

Authentic leadership. It’s a concept that feels so simple, yet it can be incredibly hard to embody. I’ve spoken about it for years, but I still find myself wrestling with it. How do I step into who I am now, while also grappling with how others perceive me? How do I embrace my evolving self?

My name is Lisa Regoli, and I’m a first-generation Jamaican American. My parents moved to Boca Raton, Florida, searching for opportunity. Boca Raton in the 80s was predominantly white and Jewish, and as a proud Jamaican girl, I was constantly aware of how different I looked and felt. I still remember the first time someone pointed it out to me—that I was different. Shame washed over me, and at that moment, I didn’t understand it. But now I know, that was shame's first knock at my door.

I felt torn. At home, I was surrounded by my culture—our food, our music, the accent in my parents' voices. But at school, I wanted to belong. I avoided the shows my parents watched because it felt like a betrayal of my desire to fit in. I practiced how to speak in front of the mirror, desperately wanting to erase my accent, to be “like everyone else.” The weight of shame was heavy, and I didn’t have the words to explain it. How could I embrace my culture when it wasn’t reflected in the space I spent most of my time?

I asked my mom to relax my hair so I could fit in. I even made sure to do things like wetting the edges of my hair to mimic the look the other girls had, not realizing I was damaging what my mother had carefully styled. The desire to belong was stronger than the desire to be myself. Shame told me that who I was wasn’t enough.

And then high school came. Finally, there were more people of color, and I thought—this is it. I’ll fit in now. But instead of feeling seen, I heard comments like, “You talk white,” or “You’ve got too many white friends.” The shame that I wasn’t “Jamaican enough” replaced the earlier feeling of not being “American enough.”

That’s the thing about shame—it has a way of shape-shifting, evolving as we evolve.

Brené Brown often says, “Shame is the fear of disconnection.” I lived that fear for years. I’ve spent most of my life wrestling with the question: How do I present myself so that I’ll be accepted?

Even now, at 42, I’m aware of how I walk into rooms. That little voice of shame whispers, Are they going to see me for who I am? Am I enough? I often get asked why I’m quiet, and the truth is, I’m filtering. I’m filtering out what I think will make people like me more, or at least, not reject me.

Recently, I did an exercise with some girlfriends, and the prompt was, “The story I’m telling myself is...” My story? That I’m not enough. That people may judge me, and that they won’t accept me for who I am.

Here’s the irony: If I could look at myself the way I look at that younger version of me in old photographs, I would never say she’s not enough. I would see her for what she is—a girl who just wants to belong, to be seen. And what I realized in that moment is this: She was seen. I was seen.

But shame tries to tell us otherwise. It tells us that to be accepted, we must filter, hide, or change ourselves. And when you’re navigating transitions—whether in life or leadership—it gets even harder to step into who you truly are. Shame makes us believe we’re failing when we evolve, when we grow into something new.

But the truth is, evolution is part of authenticity.

Brené talks about vulnerability as the birthplace of innovation, creativity, and change. But vulnerability can feel impossible when shame is the loudest voice in the room. And yet, the very essence of authentic leadership is vulnerability. It’s about showing up, even when we’re uncertain or uncomfortable.

So what does that mean for me? As a leader, I’ve come to realize that authenticity isn’t about having all the answers or fitting into some preconceived mold. It’s about owning my story, embracing who I am, and letting go of the fear that I need to be something else to be enough.

In corporate settings, I still sometimes hear, “Do you want the real response, or should I give you the HR response?” It’s frustrating. It reminds me that people expect me to fit into a box. But I’ve come to understand that leadership is about choosing to show up, even when it’s messy, even when people misunderstand you.

Shame thrives in silence, but leadership requires us to speak up. So, here’s what I’d say to my younger self: You are doing great work. You are enough. And here’s what I say to myself now: You’re allowed to be seen, fully and unapologetically. Your story is worthy, and your leadership is not defined by other people’s expectations.

As Brené teaches, our stories of struggle are what make us human. And they are what make us leaders. So, for those of you walking into rooms with doubt, wondering if you’re enough—remember this: You are.