The Ugly Middle: What No One Tells High-Achieving Leaders About Starting Over

You were built for impact, but are you prepared to be unseen while you build it?

The Lie You’ve Been Sold

In the corporate world, you’ve mastered success. You’re respected. Competent. Accomplished.

So when you decide to step out and launch something of your own, the assumption is: you’ll crush it. But here’s what most don’t realize until it’s too late:

👉 Success in corporate doesn’t guarantee stamina in entrepreneurship.
👉 The traits that made you excellent—control, structure, predictability—may be the very things that work against you now.

From the Corner Office to the Starting Line

When I left a thriving career in healthcare to launch The Wachira Group, I brought with me almost two decades of experience, a powerful network, and relentless drive.

What didn’t I expect?
To be hand-labeling bottles at 6:00 AM.
To walk into tasting rooms where no one expected a Black woman to be the founder.
To pitch my wine brand 30 times and hear “no” 30 times!

My titles didn’t matter. My accolades didn’t either.
👉Because startups demand humility over pedigree.
👉They require grit—not just goals.

Welcome to the “Ugly Middle”

This is the silent, uncomfortable stretch between launch and legacy
Where momentum is invisible. Where doubt creeps in. Where the wins are too small to post about, but too real to ignore.

Most high achievers panic here. Not because they aren’t capable—but because they’re addicted to certainty.

In the Ugly Middle, there’s no playbook. Just decisions. Risks. And a quiet discipline that says, “keep going“.

What Grit Really Looks Like

Forget the Instagram version of resilience.

Grit is:

👉Rejection without retaliation.

👉Starting over without external validation.

👉Sticking to the mission when the market isn’t paying attention.

👉I’ve learned: You don’t grow into grit. You get ground into it.

And it’s in this space—where no one is watching—that you build a brand and a backbone.

Resilience Is Not a Hashtag. It’s a Practice

There was a day I cried in my car before a wine event. Too exhausted but I still needed to Show Up.
The wine was perfect. The moment wasn’t.

That moment taught me something that no executive seminar ever did:

👉Resilience isn’t about bouncing back. It’s about staying upright when there’s no applause.

It’s finding your worth in the work, not the win. And it’s trusting that what you’re building has value—even when others can’t see it yet.

The Shift: From Excellence to Endurance

The biggest emotional pivot for corporate leaders who become founders is this:

👉You are not broken. You are becoming.

You are unlearning habits built for predictability so you can lead in uncertainty. You are trading instant respect for long-term impact.

And you are finding out what it means to lead without a title—only vision, values, and voice.

You’re Not Alone

To the leaders building in silence, doubting in the dark, or growing through rejection:

👉Stay in the Ugly Middle.

It’s not a detour.
It’s not a failure.
It’s the work.

Because if you can survive this stretch, you don’t just launch a business. You build something that outlasts you!

Let’s Talk

Have you experienced your “Ugly Middle” yet? Are you a high performer learning how to fail forward?

Reply in the comments or Contact Me—I’d love to hear your story and share the journey.

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