
A Note from Our Founder
If you've ever looked at another founder and wondered why they seem so certain while you're still figuring it out, this one is for you.
Real confidence doesn't show up before the work. It grows through it. Through solving hard problems, surviving difficult seasons, and continuing to show up even when the outcome isn't clear. What looks like confidence from the outside is often just competence that's been building quietly for longer than anyone noticed.
This week's Field Note goes straight at the gap between where you are and where you think you should be, and why you might not be as far behind as you feel.
Plan Your Week
New Hello Chaos Podcast
The habits that built your company are the same ones quietly capping it.
Debbie Simmons, CEO of AnchorPoint, grew a multimillion dollar organization on control, hustle, and pure willpower until her body shut down and forced a reckoning. What she learned about why high capacity founders actually burn out flips the grit story on its head, and the fix is not what you'd expect.
Hear how she turned chaos into a structure trust can hold, and why it matters if you're building something of your own.
Is your voice missing? Speak Up.
Do you have an entrepreneur story to tell? A point to make? An idea to share? We want to hear from you! Sign up to be a Hello Chaos guest today.
How To: Explain Your “Crazy” Pivot

Tina Zwolinki’s 25 years as a founder of branding and marketing agency, ZWO, plus Cynthia Jenkins’ five years as a partner at ZWO (after a couple of decades in media and marketing) don’t seem to add up to a workforce education tech company.
The two women founded skillsgapp anyway.
Through skillsgapp games, Gen Z players learn about career opportunities and build skills that have been sorely missing in the talent pipeline for lucrative jobs in manufacturing, cybersecurity, life science and more. By jumping into innovation way outside of their industry, Jenkins and Zwolinski are adding a story that’s been sorely missing from the gaming entrepreneur narrative.
The team at ZWO had come to realize marketing wasn’t enough to help their clients connect with the young workforce they were trying to lure. But in brainstorming the solution, Zwolinski ended up rethinking her entire business. She’d decided to fold up ZWO and pivot to gaming full-time.
But first, Zwolinski had some ‘splaining to do. Coworkers, clients, friends and family would have questions. She shares with OrangeWIP exactly how she conducted those tough conversations.
Resource Spotlight
Every successful business starts with someone willing to take the first step.
That's exactly where Village Launch comes in. They help aspiring and early-stage entrepreneurs turn ideas into action through a 10-week academy focused on the practical skills needed to build a business.
But the program is only part of the value. Village Launch also connects founders with a community of entrepreneurs, mentors, and innovators who understand the challenges of starting from scratch.
If you've been waiting for the right time or the right support to launch your idea, this is a resource worth exploring.


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