September 22 - 26 | Monday - Friday, 10AM - 11:30AM
The Confidence To Coach Tiny Challenge Shadow Seat
Are You Running Tiny Challenges But Feeling Like You're Drowning in the Process?
You've got the passion. You've got the expertise. You've even got the courage to put yourself out there with your own Tiny Challenges.
But here's what's really happening behind the scenes:
You've got the passion. You've got the expertise. You've even got the courage to put yourself out there with your own Tiny Challenges.
You're overwhelmed by all the moving parts and wondering if you're doing it "right"
You're second-guessing your message and whether anyone actually cares what you have to say
You're losing confidence with each challenge that doesn't quite hit the mark
Sound familiar? You're not alone, my friend.
The truth is, most coaches launch Tiny Challenges without a solid foundation and then wonder why they're exhausted, confused, and ready to throw in the towel.
What If You Could Run Tiny Challenges with Clarity, Confidence, and Actual Results?
I'm Caitlin
I've helped countless coaches transform their Tiny Challenges from overwhelming experiments into powerful, profit-generating machines.
As a Performance One Coach, I've seen exactly what separates the coaches who thrive from those who burn out.
Here's what I know for certain: The problem isn't your expertise or your passion.
The problem is you're missing the foundational elements that make Tiny Challenges actually work.
And that's exactly what we're going to fix together.
September 22 - 26 | Monday - Friday, 10AM - 11:30AM
This isn't just another training where you take notes and hope for the best. This is your chance to go behind the scenes of a real, live Tiny Challenge and see exactly how it's done.
You'll shadow my proven "Confidence To Coach" challenge and discover the exact framework, messaging, and structure that consistently generates engaged audiences and eager buyers.
Here's What You'll Experience:
Watch how I speak directly to my ideal client's deepest pain points
See the exact language that makes people think "She's talking directly to me!"
Discover how to craft messaging that cuts through the noise and grabs attention
Perfect Your Ascension & Offer Strategy
Observe the seamless flow from free challenge to paid programme
Learn how to plant seeds throughout your challenge that naturally lead to sales
See how to make offers that feel like gifts, not pushy sales pitches
Get the exact framework for planning content that builds momentum day by day
Watch how each session connects to create an irresistible journey
Learn the secret to keeping participants engaged from start to finish
This Shadow Seat Experience is Perfect for You If:
You're part of the Underdog Academy and ready to level up your Tiny Challenges
You've tried running challenges before but felt overwhelmed or unsure
You know you have something valuable to share but struggle with how to package it
You're tired of second-guessing yourself and want to see how it's really done
What Other Coaches Are Saying About My Training:
"Thank you so much for being kind and making this available. I know it will have a tremendous impact on me and I am ready to help people transform."
- Paul R., Coach
"Caitlin, thanks again for the opportunity to shadow your session. It gave me a lot of insight into the process and was genuinely valuable."
- Kim C., Author & Coach
"I am thoroughly enjoying being a part of the shadow seat gallery and observing the Tiny Challenge in action. Seeing things live is so much better than a recording. I appreciate you for the work you do."
- Bron E., Coach
Here's What You'll Walk Away With:
Crystal Clear Confidence in how to structure and run your own Tiny Challenges
A Refined Message that speaks directly to your ideal client's heart and pain points
Unshakeable Certainty about your process, your value, and your ability to deliver transformation
Instead of feeling overwhelmed and scattered, you'll have the clarity and confidence to run challenges that actually convert.
Ready to Shadow a Challenge That Actually Works?
This exclusive shadow seat opportunity is limited to Underdog Academy members only, and spots are filling fast.
Don't spend another moment wondering if you're doing it right. Come and see exactly how it's done.
September 22 - 26 | Monday - Friday, 10AM - 11:30AM
Limited spots available to ensure you get the most out of this experience
P.S. Remember, the coaches who succeed aren't the ones with the most qualifications or the biggest followings. They're the ones who have clarity, confidence, and a proven system. This shadow seat experience will give you all three.
© 2025 Caitlin Winch Coaching