The Jump Moment
The Jump Moment
Podcast Description
What does it take to go from dreaming to doing? The Jump Moment. Every creative who’s made the leap to freelance has had a Jump Moment. Sometimes it’s a bold, unmistakable event. Other times, it sneaks up slowly, shaped by life’s circumstances or a quiet realization.And if you’re dreaming of turning your creative hobby into a business, chances are you’re searching for that moment, wondering, “Is now the time to jump?”In each episode, I sit down with creatives and entrepreneurs to explore their Jump Moment—the fears they faced, the courage it took, and the lessons they learned along the way.These stories will inspire you, show you that you’re not alone, and give you the tools and confidence to take your next step.Your Jump Moment might be just around the corner. Let’s get you ready for it.
Podcast Insights
Content Themes
This podcast delves into themes such as overcoming fear, finding courage, and learning valuable lessons through personal narratives of freelancers. Topics include the role of mentorship, managing imposter syndrome, and the significance of community support. Examples from episodes include Laura Howe's experience with burnout leading to the creation of Hope Made Strong and Micah Thomas's transition from a church media director to starting Impact Merch.
What does it take to go from dreaming to doing?
The Jump Moment.
Every creative who’s made the leap to freelance has had a Jump Moment. Sometimes it’s a bold, unmistakable event. Other times, it sneaks up slowly, shaped by life’s circumstances or a quiet realization.
And if you’re dreaming of turning your creative hobby into a business, chances are you’re searching for that moment, wondering, “Is now the time to jump?”
In each episode, I sit down with creatives and entrepreneurs to explore their Jump Moment—the fears they faced, the courage it took, and the lessons they learned along the way.
These stories will inspire you, show you that you’re not alone, and give you the tools and confidence to take your next step.
Your Jump Moment might be just around the corner. Let’s get you ready for it.
Recommended resource: The Coaching Habit: Say Less, Ask More, and Change the Way You Lead Forever by Michael Bungay Stanier.
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In this episode of The Jump Moment, Matt sits down with Casey Watts, an educator turned consultant, speaker, and author, who helps leaders create meetings that actually matter. Casey shares how her career evolved from teaching to leadership to full-time business ownership—and how clarity became the guiding thread. She also opens up about the fears, financial hurdles, and support systems that made her jump possible. If you’re wrestling with fulfillment, regret, or the “right time” to take the leap, this conversation is for you.
Episode Highlights:
- Why bad meetings are often a symptom of a lack of clarity.
- How side hustles can reveal your through-line and shape your eventual business.
- The importance of knowing when you’re no longer showing up fully at work.
- Why regret is often the greater risk than failure.
- Two pieces of advice Casey would give her younger self.
About Casey:
Casey Watts is a passionate speaker, author, and thought leader in team leadership with over 20 years in education and 10 years of experience coaching educators, entrepreneurs, and leaders. She is the creator of the Clarity Cycle Framework, helping leaders bridge gaps, foster commitment, and create sustainable alignment. Casey is also the founder and host of The Catching Up with Casey podcast, where she and her guests bring clarity to the seemingly small things in leadership that make a big difference.
Connect with Casey:
Website: https://www.catchingupwithcasey.com/
LinkedIn: https://www.linkedin.com/in/catchupwithcasey
Instagram: https://www.instagram.com/catchupwithcasey
Youtube: https://www.youtube.com/@catchupwithcasey
Explore the Jump to Freelance community, 1:1 coaching, and more at jumptofreelance.com. Take your first step today!
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