What Carolyn Bessette Teaches Us About Leadership

If you’ve been anywhere near a television or a social media feed lately, you’ve seen her.

Carolyn Bessette-Kennedy. Ivory slip dress. That jaw. That style. That presence.

The FX series has reignited a full-blown cultural obsession. And honestly? I’m obsessed too.

But I don’t think it’s just about the fashion or the tragedy or the mythology of JFK Jr. I think we’re obsessed with Carolyn Bessette because of something more elusive. 

Carolyn remained fully Carolyn. 

In a world that was constantly trying to define her as JFK Jr.’s girlfriend, then his wife, as a Kennedy, as a public figure expected to perform a very specific role, Carolyn Bessette remained stubbornly, almost defiantly, herself. And that refusal to abandon who she was in order to fit someone else’s expectations is what made her magnetic. (It’s also what made John so crazy about her.)

Here’s what strikes me as a leadership coach: what we’re witnessing in that obsession is a masterclass in the difference between who you’re being and what you’re doing.

The Difference Between Being and Doing (And Why Self Leadership Starts Here)

Most of us spend our entire careers focused on the doing.

What do I need to accomplish? What boxes do I need to check? What does my boss, my board, my industry, my partner expect me to DO to prove I belong here?

We become very good at performing the role and adapting to meet whoever’s in front of us.

And it works. For a while. We get the promotion. We get the title. We get the recognition.

But somewhere along the way, we stop asking ourselves a much more important question:

Who do I want to be as I’m doing all of this?

That’s the question Carolyn never seemed to stop asking. And the answer was always herself. Fully. Without apology.

She wasn’t trying to become a Kennedy. She wasn’t performing warmth or accessibility or whatever role the public wanted from her. She was a woman who knew exactly who she was, what she valued, and how she wanted to show up. And she did that, whether she was navigating a media circus or standing next to one of the most recognizable men in the world.

That’s not effortless. That’s intentional self leadership. 

What Self-Abandonment Actually Looks Like

I see the opposite of Carolyn Bessette every single day.

Brilliant, accomplished women. Directors, executives, entrepreneurs. Women who have climbed ladders and earned seats at tables that they fought hard to get. But too often, they’ve done it by following the example of leadership that came before them without asking themselves if that’s what leadership looks like to them. 

They’ve made themselves smaller in meetings so they don’t seem too aggressive. They’ve softened their opinions to avoid conflict, said yes when they really wanted to say no, and spent years making sure everyone in the room was comfortable — everyone except themselves.

And please hear me LOUD and CLEAR - this is NOT a character flaw. It’s a survival strategy. We came up in a world that told us this was who we had to be in order to get ahead. And for a lot of us, it worked for so long that we forgot we were doing it.

But it is not sustainable. It has a HUGE cost. 

The cost isn’t just exhaustion, though that’s real. The cost is that you start to lose the thread back to yourself. You stop knowing what you actually think, what you actually want, what you’d actually do if you weren’t worried about how it would land.

You stop being true to you. And you start performing the role you think will lead you to success. 

Who You’re Being Is the Leadership Work

This is where a lot of  leadership work goes sideways.

We treat it like another item on the to-do list.

Read the book.
Do the journaling.
Attend the retreat.
Check the box.

And none of it actually changes how we show up in the room because we’re still focused on what we’re doing instead of who we’re being.

Who you’re being is about knowing who you are and what’s important to you to live a fulfilled life. It’s not only about what you’re doing. It’s about how you’re doing it. It’s about the values you’re actually living and the boundaries you create to honor them. It’s about whether you’re leading from the inside out or just executing someone else’s playbook with your name on it.

What does it look like to lead from who you’re being?

It looks like the client I worked with who stopped rehearsing what she was going to say in every meeting and started just… speaking. Trusting that what she thought actually mattered. She didn’t get louder. She got clearer. And people started listening differently.

It looks like the woman who finally stopped pretending to be fine with a dynamic at work that was costing her her confidence, and had the conversation she’d been avoiding for two years. Not because she had a perfect script. Because she knew who she was, and staying silent was no longer consistent with that.

It looks like a woman who walks into the room and knows what she brings. She doesn’t need the room to confirm it.

That’s the energy Carolyn Bessette had. And yes…that’s also what made JFK Jr. obsessed with her. Because there is nothing more magnetic than a person who is fully, unapologetically themselves.

So here’s the question to be asking yourself…

It’s not what are you doing to get ahead. It’s not are you meeting your quarterly goals.

Who are you being as you do those things? 

When you walk into a meeting, are you the version of yourself who had a really smart thought in the shower that morning? Or are you the edited version - the one who decided somewhere between the shower and the conference room that maybe it wasn't worth saying after all.

And if it's the latter, I'd love for you to get curious about why. Because that question is the beginning of real self leadership. The kind that actually changes how you move through the world. And the act of changing how you move through the world has the potential to actually change the world. 

We're obsessed with Carolyn Bessette because she didn't shrink. But here's the thing - she's not the exception. She's the reminder.

You already know who you are. The question is whether you're willing to stop apologizing for her.

Want to focus more on who you’re being? One of the things that gets in the way the most is the voice of your inner critic. I created a free guide — How to Discover and Work With Your Inner Critic.