You don’t always know when a breakthrough is coming.
Sometimes it arrives wrapped in failure. Other times in frustration. Sometimes in a moment so odd or unexpected, you don’t realize it was the turning point until long after the dust settles.
In the digital business world, we love a good before-and-after. The glossy story. The clean arc.
But that’s not how it works for most people.
Ask around, and you’ll hear stories of surprise pivots, emotional upheavals, and random experiments that reshaped everything.
So we did. And these are their stories.
The 24-Hour Party That Saved a Business
When Donna Clark’s art journaling membership tanked during the early days of the pandemic, she could have called it a loss.
Instead, she threw a 24-hour virtual art party.
"I didn’t know what else to do. I needed connection. I needed community. So I just put the invite out and hoped someone would show up."
More than 5,000 people joined.
It didn’t just boost her morale — it rebuilt her list, brought in new customers, and created a ripple of inspiration across her audience.
Sometimes the best move isn’t to fix what’s broken. It’s to try something radically different, even if it feels a little chaotic.
The Danger of Giving It Away for Free
Cody Burch thought he was doing everything right. He hosted a free online event. Promoted it to his list. Waited.
But almost no one showed.
"It was humbling. I realized people don’t value what they don’t invest in — even if it’s just a few dollars."
Cody adjusted. He began charging even $7 for access to events. And just like that, people started showing up.
The money wasn’t the driver — commitment was. And that small tweak changed his entire approach to audience engagement.
Systems Built on Vacation Chaos
Larissa Uredi was on a long-awaited vacation when things fell apart.
"One of our contractors completely ignored their assignments. I came back to a mess."
It wasn’t just a hiccup — it was a turning point.
That one misstep made Larissa realize how fragile her systems were. She implemented project management tools, cross-trained her team, and restructured how work got done.
What could’ve been just a rough Monday became the seed for a stronger, more resilient business.
When the Launch Flops (Hard)
Ken Fleisher had a vision: a paid membership built around short, impactful videos.
He spent time — and money — building it out, creating bonuses, and promoting it through contests.
"And then… only three people signed up. I was crushed."
But it taught him one of his most valuable lessons:
"Never build the whole thing before testing the idea."
Today, Ken validates everything with tiny experiments. It’s not glamorous, but it works.
Sometimes the smartest path forward starts with falling flat.
The Breakdown That Led to the Breakthrough
Jamie Bright built a seven-figure photography business — and lost it when the pandemic hit.
"It was devastating. I had built my identity around that business. I didn’t know what came next."
Turns out, what came next was even better.
Jamie pivoted to coaching. She began helping other creatives build sustainable businesses — and found a calling that felt more aligned than anything she’d done before.
Breakdowns are painful. But sometimes they clear space for something more true.
Planting New Roots (Literally)
Asia Sharif-Clark used to run an in-person art school. When COVID shut everything down, she hit pause.
And then she started gardening.
"I didn’t mean to turn it into a business. But I couldn’t stop sharing what I was learning. And people wanted more."
Her new online gardening business didn’t just re-energize her — it rebuilt her confidence, her income, and her joy.
That’s the thing about pivots. They often grow quietly — like seeds — before they ever show their leaves.
The Power of Story Over Steps
Grace Bell had built a weight-loss program rooted in structure, steps, and guidance.
"But what people really wanted wasn’t the roadmap. It was me. My story. My honesty."
When she started sharing more of her personal experience — her struggles, her breakthroughs — the work landed differently. People connected. Signed up. Stuck around.
Her program didn’t change much. But the way she showed up in it did.
Sometimes the most valuable piece of your business is the one you’ve been keeping quiet.
Final Thought: Breakthroughs Rarely Look Like Breakthroughs
No one ever tells these stories on a highlight reel.
They start as detours. Setbacks. Even failures.
But for the entrepreneurs who lived them, they became turning points.
So if you’re in a season that feels uncertain — if things aren’t going as planned — maybe you’re not off-track. Maybe you’re just between breakthroughs.
Give it time. Let it teach you. Then build something better.