Cara Flynn - International Women’s Day

For International Women’s Day this year, I reached out to a handful of women I deeply respect.

This is in no way a “top list.” I know so many extraordinary women - and there are countless more I don’t yet know.

These women come from different industries, backgrounds, and seasons of life. Coaches. Writers. Leaders. Career women. Creatives.

I asked them a few powerful questions about leadership, success, unlearning, and becoming.

And today, I want to introduce you to Cara Flynn.

When Cara sent over her answers, she added a quick note:

“Lemme know if you want something more fun lol.”

Which tells you quite a bit about her right away.

There’s a certain kind of confidence in that line - the kind that doesn’t take itself too seriously.

If you asked her what she does at dinner, Cara would likely say something like this:

“I work in fundraising in the nonprofit world - building relationships with philanthropists and funders so we can support some amazing nonprofits’ programs and initiatives.”

In other words, she lives in the space where generosity meets impact - helping connect the people who want to make a difference with the organizations doing meaningful work.

It’s the kind of work that often happens quietly, but without it, a lot of incredible programs simply wouldn’t exist.

When I asked her what being a woman in her leadership space means to her, her answer was simple and direct:

Being yourself.

Embracing projects and challenges that align with your interests and passions.

And making sure that your voice is heard.

That clarity carries through to something she’s had to unlearn along the way.

Her answer?

“Don’t apologize!”

Short. Direct. Effective.

Sometimes the most powerful shifts come in the smallest sentences.

Right now, Cara says she’s stretching in a different direction - one that many ambitious women eventually find themselves navigating.

She’s developing more of her identity outside of work.

After several years of health challenges, she says she’s gained a level of perspective she might not otherwise have encountered until much later in life.

Those experiences shifted something.

They reminded her that life is bigger than productivity, and that who we are outside our roles matters just as much as what we accomplish inside them.

And sometimes it takes a moment that slows us down to see that clearly.

When I asked her what success feels like in her body these days, her answer felt beautifully grounded.

“Success feels like I tried my hardest and I’m happy.

At the end of the day, I love the moments when I see positive outcomes stemming from my work. That’s what makes the hard moments worth it.”

There’s something refreshingly honest about that definition.

Not perfection. Not status.

Just effort, impact, and the satisfaction of knowing it mattered.

And when it comes to what she wishes more women believed about themselves, Cara didn’t hesitate.

She wishes more women believed they already possess the skills and knowledge to go after what they want.

That they don’t need to wait until they feel completely ready.

Finally, I asked her to finish this sentence:

“I am a woman who…”

Her answer was thoughtful and honest:

“I am a woman who is finding a balance between pushing for more and being content.”

Which might be one of the most honest answers in this entire series.

You can find Cara through her work in the nonprofit world, building the relationships that help meaningful programs grow and thrive.

There are so many extraordinary women in my world - and so many more beyond it - who aren’t represented in this small series.

Consider this a celebration of them, too.

And in Cara’s words:

Find the balance between pushing for more - and being content with where you are.