Episode 003: For When It's Time To Embrace Your Success

Why is it that when success starts to feel real, something inside you still wants to play small?

In this week’s episode, Kat explores a common struggle that many high-achieving leaders face when it’s time to embrace their success.

After a conversation with one of the design interns at Afternoon Culture, she realized how often founders hesitate right when things begin to take off. Kat shares the story of her own early days with Afternoon Culture and how imposter syndrome can show up in subtle ways. For many founders, it’s not a loud, obvious fear, but a quiet instinct to play small when real opportunities start to emerge. 

She also discusses how this hesitation is often amplified for people of color, who face additional layers of societal expectations, microaggressions, and systemic challenges.

If you’re a high achiever who’s ever struggled with self-doubt or felt like a fraud, this one’s for you.

Full Transcript

Last week I was in a meeting with two of our design interns. We’re in the middle of refreshing the Afternoon Culture brand, and we were reviewing new business card designs.

At one point, Maggie, one of the interns, looked at me and asked,
“Why doesn’t your card say CEO?”

I laughed and said something like,
“Well, titles have always felt weird. We’re a small team. I’m the founder, the creative director, the strategist—I wear whatever hat needs to be worn that day.”

And she just said,
“Yeah… but you’re also the CEO.”

That moment stayed with me.

For this episode, I want to talk about that quiet discomfort that shows up when it’s time to embrace all that you’ve accomplished—but something gets in the way.

Because I know I’m not the only one who’s been here.
Let’s get into it.

A few years ago, I started to notice something at Afternoon Culture that gave me a little pause.

I’d meet an incredibly charismatic founder with a powerful mission and a deep desire to build a business around it.

Most of the time, it would be a woman who had left an unfulfilling job to create something that felt personal, culturally significant, and deeply rooted in her values. She was also bootstrapping her way through it with no funding, all hustle, and good vibes.

And then, something big would happen. She’d get featured in a major publication like Forbes, Inc., or The New York Times, or land a major partnership with a Fortune 500 company.

That moment would give her the confidence to get serious about her brand. So she’d reach out to us, and we’d begin working together on a rebrand.

We’d kick off the project and start re-evaluating everything—the brand’s purpose, its positioning, the way it told its story, and the experience. The energy would be incredible and we’d tapped into great momentum.

We’d move through a discovery phase and begin laying the foundation for the brand’s evolution.

But then, right when it was time to define the brand—when it was time to start making major decisions about how she would show up differently—something would shift.

Suddenly, this same founder who had been so committed to the transformation would start hesitating.
Everything from finalizing a color palette, to giving feedback on messaging, or even booking a call would become much harder.

And when she showed up, she was distracted.
She’d start saying she felt unclear and that the brand didn’t make sense anymore.

And by that point, we’d already been working together for weeks.

Every time it happened, it would blindside me and my team.

I used to take it really personally. I’d wonder what I had missed or what I could have done differently.

At some point, I had read that 88% of business transformations failed—and I took that to heart.
I was determined to make every project a success.

So I’d offer more strategy sessions, more support, more revisions. I’d try everything to keep the momentum going and see the project through.

But more often than not, the founder would ghost us.
The work would stall out, and the rebrand would be left unfinished.

And then—almost like clockwork—a year later, they’d reach back out.
This time with context and major breakthroughs.
They’d explain why they had to step away—and that they were ready to start again.

For years, I felt so much frustration whenever I saw a founder abandon a project.

There have even been times when I would question whether my process was actually transformative.

But that moment with Maggie—my intern asking why my card didn’t say “CEO”—made me realize something about embracing success.

We’re getting ready to celebrate seven years of Afternoon Culture.
Seven years of wins, lessons, growth, and transformation.

I’ve done a lot of personal work to be more confident and stand firm in my accomplishments:
therapy, executive coaching, a robust journaling practice, and lots of self-reflection.

And still, I catch myself playing small and downplaying the success I’ve worked really hard for.

The truth is that I haven’t been calling myself what I actually am—not because I didn’t realize my role,
but because some part of me was still uncomfortable with claiming it.

And when I sat with that discomfort, I realized:
I’ve seen this before.

It’s the same thing I saw in the founders we’ve worked with over the years.

That quiet hesitation.
That subtle fear that rolls in just as things are starting to click.
That instinct to pull back—right when it’s time to stand in your power.

It used to confuse me.
I’d wonder why someone so brilliant and so visionary would start second-guessing everything the moment their brand was about to evolve.

But in that moment with Maggie, I saw it in myself.

I now know that the founders I have collaborated with weren’t stuck because they lacked clarity.
They were stuck because embracing success felt more vulnerable than hiding and staying small.

Because once you say,
“This is who I am. This is what I do. This is where I’m going”—you’re in it.

It’s the point of no return.
You can’t hide behind potential anymore. You can’t fall back on just winging it.

You’ve declared it, and now the world gets to respond.

And that?
That’s terrifying in a way failure never was.

I started Afternoon Culture with a few hundred dollars and a quiet curiosity to see if it could last past six months.

I was ready for the struggle and comfortable with setbacks.
I knew how to hustle through the hard times.

But when things started working—when real opportunities started showing up—I wasn’t sure how to embrace all of its potential.

Every time Afternoon Culture hit a new milestone, I’d get more careful and more cautious.
I’d shrink the dream just a little, convinced the stakes were higher now.

I told myself I was being “realistic,” that I was making “better plans.”
I called it being strategic and grounded.

But if I’m being honest?
It was self-doubt.

Imposter syndrome doesn’t always show up as something that’s loud and pronounced.

Sometimes it’s quiet.

It’s in overthinking and overplanning.
Perfectionism.
Needing to learn one more thing before you start.
Believing you have to get it right the first time.
Feeling like you have to do it all on your own.
Waiting for the other shoe to drop.

In my case, imposter syndrome crept in as the thought that since I had already failed, it could happen again at any moment.

So I started really small—my only goal was to make it to six months.

I didn’t even call myself a CEO, even though that’s exactly what I was.

I told myself I was just being humble, just staying grounded.
But the truth is, I was afraid to fully step into the role because I wasn’t sure I could live up to it.

When things started to take off, I wasn’t really prepared for it,
and I let self-doubt squeeze out the magic of every major win.

For the founders we collaborated with, imposter syndrome often showed up as hesitation—like once they moved from keeping things casual and behind the scenes to stepping into more visibility, the pressure to get everything right became overwhelming.

It looked different, but we were reacting to the same feeling.

We didn’t feel good enough to celebrate our wins and enjoy our success.
And we were putting an immense amount of pressure on ourselves.

Imposter syndrome gets talked about a lot these days.
You see it in articles, hear it on panels, and feel it come up in conversations with friends.

And while studies say that up to 80% of people have experienced it, we also need to recognize that imposter syndrome isn’t one-size-fits-all.

For people of color, it often comes with extra layers.

It’s not just about self-doubt or questioning your worth.

It’s what I think of as imposter syndrome plus—a mix of societal expectations, lack of representation, microaggressions, and navigating systems that weren’t designed with us in mind.

So if it feels harder, it probably is.

Between where you are and where you want to be, there’s the work you have to do:
the planning, the skill-building, the strategizing.

But there’s also the internal shift—
the part where you give yourself room to grow, to be seen, and to expand into your full potential.

And that’s no small thing.

Especially when you’re the first, or the only, or the one everyone is quietly watching.

That kind of pressure is real,
and it requires a deeper kind of self-compassion.

Because if trailblazing is the gift,
imposter syndrome is the curse that makes you question whether you’re worthy of it.