The Jump Moment

Matt Curtis
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  • UPDATED BIWEEKLY

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.

  1. NOV 18

    The first 90 days of your freelance business

    What's your biggest takeaway? In this episode of The Jump Moment, Matt Curtis walks through what it really looks like to start a freelance business. Whether you’re preparing to leave your job or already in your first few months as a freelancer, this episode outlines a 90-day roadmap to help you build in a way that is realistic and builds momentum.  Matt shares the 12-week framework he walks through in the Christian Creative group to help freelancers set a manageable building pace. If you’ve ever tried to cram an entire business build into a long weekend or holiday break, this episode will help you slow down, plan smarter, and building a way that gains momentum over time. The 90-Day Jump Start Plan Weeks 1–6: Building the Foundation 1. Discover Your Why – Identify what drives you and the people you’re called to serve. 2. Build and Price Your Offer – Connect your skills to your client’s real-world problems. 3. Short-Term Marketing – Create a plan to start sharing your offer right away. 4. Personal Systems – Build systems that help you protect you time outside of working in your business. 5. Contracts and Taxes – Understand simple contracts and tax implications as a business. 6. Professional Systems – Build workflows, client onboarding, and invoicing systems to support the operation of your business. Weeks 7–12: Sustaining Momentum 7. Mid- and Long-Term Marketing – Build a marketing planning focused on mid-term and long-term investments. 8. Money in Business – Learn how to make wise financial decisions that protect your future. 9. The Heart of a Freelancer – Learn how to work well with clients, be gracious and humble, and create healthy boundaries. 10. Protecting Imagination – Prioritizing rest, creativity, and long term creative health. 11. Developing your Skills – Ongoing growth and development as a creative. 12. Evaluate and Pivot – Use a 90-day planning rhythm to review, refine, and set your next goals. Resources Mentioned Traction by Gino Wickman — A powerful guide to building and running your business in 90-day cycles. Affiliate link: https://amzn.to/4a0fY7PQuarterly Workflow Worksheet — Matt’s free tool to help you plan and evaluate your next 90 days. Download.Join the Christian Creative group on Skool. Learn more about 1:1 coaching or find tools to help with your jump to freelance at https://www.lunchtimeheroes.co/coaching.

    34 min

  2. NOV 4

    From Meetings to Meaning | Casey Watts on Building a Business with Purpose

    What's your biggest takeaway? Recommended resource: The Coaching Habit: Say Less, Ask More, and Change the Way You Lead Forever by Michael Bungay Stanier. ---------- 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 Join the Christian Creative group on Skool. Learn more about 1:1 coaching or find tools to help with your jump to freelance at https://www.lunchtimeheroes.co/coaching.

    28 min

  3. OCT 21

    The Secret to Creative Success Might Be in Your Schedule

    What's your biggest takeaway? What if the key to unlocking success in your creative business isn’t another tool or strategy... but it's your schedule? In this episode, Matt Curtis explores how time management shapes both creative freedom and business growth for freelancers and staff creatives alike. You’ll learn why your calendar might be the most important tool in your creative toolkit—and how managing your schedule with wisdom and intention can help you align your work with your values. Matt shares practical steps from his Tools for Christian Creatives series, including a simple, printable worksheet that helps you uncover where your time really goes. Whether you feel like your day is out of your control or you’re struggling to stay disciplined as a freelancer, this conversation will help you manage reality, build sustainable habits, and protect the things that matter most—your faith, your relationships, and your calling. Free Resource: Download the Weekly Schedule Planner mentioned in this episode and build your schedule your time with purpose. Download now Join the Christian Creative group on Skool. Learn more about 1:1 coaching or find tools to help with your jump to freelance at https://www.lunchtimeheroes.co/coaching.

    24 min

  4. SEP 23

    High Performance without Burnout | with Frank and Sabrina Szabo

    What's your biggest takeaway? Many believe that burnout is just about overworking. But in many cases, burnout actually stems from being underutilized.  In this episode of The Jump Moment, I talk with Frank and Sabrina Szabo, founders of /chaynj/ (pronounced “Change”), a coaching business dedicated to helping high performers prevent and recover from burnout. We discuss the dangers of tying your identity to performance, the fears and transferable skills involved in making the jump to freelance, and the critical role of community in sustaining your business. Episode Highlights: Burnout is often about underutilization rather than overworkHigh performance can be healthy with the right rhythmsThe tension of finding transferable skills when leaving a long careerWhy fear is natural (and even helpful) when starting something newCommunity as both protection against burnout and fuel for freelancingAbout Frank and Sabrina Szabo: Frank and Sabrina Szabo are partners in life and co-founders of /chAYnj/, a coaching practice focused on those who operate under constant emotional demand and high responsibility. As a Hungarian-Brazilian team, they bring cultural depth, grounded presence, and hard-earned insight to their work. Their coaching supports individuals who hold it all together at the office, at home, and often in silence. Because they understand the weight of that role firsthand, they help clients recover clarity, agency, and a sense of self. Sabrina is a leadership coach, educator, and ICF Foundation Ambassador. She currently pursues a PhD in Intercultural Education and holds a Master’s in Global Leadership. Frank is a high-performance coach and author who has spent over twenty years supporting Olympic athletes and pressure-tested teams. In addition, he holds certifications in EQ-i 2.0® and EQ 360. Both Frank and Sabrina are ICF Professional Certified Coaches. Together, they remain committed to making emotional well-being both practical and deeply personal. If you feel like you've been holding it together while quietly burning out, check out the Own Your Shift program. This 12-week experience supports people who carry a lot and need more than just rest. We help rebuild emotional capacity, sharpen focus, and restore a sense of self through one-on-one coaching, clear structure, and measurable progress. We run the program only three times a year with six participants each time because we prioritize deep, personal support. This work comes from our own lived experience with burnout, and we’re deeply committed to helping others find steadiness again. If you're ready to stop bracing through the day and start living with more presence, they can learn more at chaynj.com. Connect with Frank and Sabrina:  LinkedIn: https://www.linkedin.com/company/chaynj/ Instagram: https://www.instagram.com/chaynj_lead/ Website: chaynj.com Frank's Book: https://amzn.to/4mwnzh4 Join the Christian Creative group on Skool. Learn more about 1:1 coaching or find tools to help with your jump to freelance at https://www.lunchtimeheroes.co/coaching.

    47 min

  5. JUL 22

    Being faithful with what’s in front of you with Jacob Dyke

    What's your biggest takeaway? When your vision feels far off and progress is slow, how do you keep going? In this episode, executive coach Jacob Dyke shares what it looked like to stay faithful with what God had placed in front of him—even when business didn’t take off right away. From working evenings at Lowe’s to give his business a fighting chance, to wrestling through identity, fear, and provision, Jacob’s story is a powerful reminder that slow progress is still progress. If you’ve ever wondered whether it’s worth it to keep building when results are delayed, this conversation will encourage you to stay the course. Episode Highlights: Why progress doesn’t always mean speedWhat it looks like to be faithful with what’s in front of youHow to balance vision for the future with intentionality in the presentWhy spiritual formation matters in the entrepreneurial journeyThe role of coaching and outside voices in finding your directionAbout Jacob Dyke: Jacob is the founder of Anchor Coaching, where he helps Christian entrepreneurs improve productivity without burnout as well as a Startups.com Advisor. Jacob writes The Anchored Entrepreneur, a newsletter you can find via his LinkedIn. Connect with Jacob Dyke: Website: http://anchorcoaching.co/ Newsletter: https://anchor-coaching.beehiiv.com LinkedIn: https://www.linkedin.com/in/jacob-dyke/ Join the Christian Creative group on Skool. Learn more about 1:1 coaching or find tools to help with your jump to freelance at https://www.lunchtimeheroes.co/coaching.

    39 min

  6. JUN 24

    From Wish to Will - How Cody Lutz Made the Jump to Entrepreneurship

    What's your biggest takeaway? In this episode of The Jump Moment, Cody Lutz shares how he moved from corporate leadership to full-time entrepreneur — and how a powerful mindset shift helped him overcome fear, redefine risk, and bet on himself. We talk about launching before you’re ready, pivoting your offer based on real audience needs, and why identity change is the foundation of every major life change. Episode Highlights: Why Cody shifted from a “wishful” mindset to a “will” mindsetThe false sense of security many employees live under — and how freelancing can actually reduce riskHow financial discipline gave Cody the freedom to take the leapWhy launching a business means listening, pivoting, and staying open to better opportunitiesThe power of rooting your work in a deeper calling or convictionAbout Cody Lutz: Cody spent 8 years running conferences around the country for a 9-figure non-profit in my 20s. Reinvented myself during COVID and got a tech support agent role in a small tech company. Became the department head a year later and tripled the department in 3 years. Made THE JUMP into full-time entrepreneurship in July of '24 to build Backyard SHREDS (home fitness for men) and now also coach other ambitious men in their own journey from "wantrepreneur" to "entrepreneur". Connect with Cody Lutz: Website: http://backyardshreds.com/ LinkedIn: https://www.linkedin.com/in/thecodylutz/ Instagram: https://www.instagram.com/backyardshreds/ Youtube: https://www.youtube.com/@BackyardSHREDS Join the Christian Creative group on Skool. Learn more about 1:1 coaching or find tools to help with your jump to freelance at https://www.lunchtimeheroes.co/coaching.

    48 min

  7. MAY 27

    Is This My Purpose? A Conversation About Leaving a Cause-Based Organization

    What's your biggest takeaway? If you’ve ever felt like the mission you're working for doesn’t match the purpose you’re carrying, this episode is for you. In Is This Even My Purpose?, Matt Curtis opens up about the unsettling moment many creatives face in cause-based roles—when the work no longer feels aligned. He shares four powerful “why drivers” that helped him move from confusion to clarity: craftsmanship, service, mission, and lifestyle. This isn’t just a reflection. It’s a roadmap. If you’ve been asking hard questions, this episode may help you find honest answers—and your next step. Episode Highlights: Why alignment matters more than loyalty when the mission that no longer fitsHow creatives slowly lose access to their full skillset in misaligned rolesFour “why” drivers that clarify your purpose: craftsmanship, service, mission, lifestyleA step-by-step reflection to help you move forwardJoin the Christian Creative group on Skool. Learn more about 1:1 coaching or find tools to help with your jump to freelance at https://www.lunchtimeheroes.co/coaching.

    26 min

  8. MAY 13

    Say yes first | How seizing one opportunity changed everything for Travis Whatley

    What's your biggest takeaway? This week’s resource is the Jump to Freelance group on Skool.  Freelancing doesn’t have to be lonely. Join a community of like-minded creatives who understand the journey you’re on. Whether you’re dreaming, planning, or building momentum after making the jump, this group offers support, live Q&A’s, and expert guidance to help you thrive—together.   Join the group. - - - Travis Whatley didn’t feel ready. He didn’t even know what WordPress was. But when someone asked if he could build a website, he said yes—and that one decision launched a freelance journey that became a thriving agency. In this episode, Travis shares how ministry, burnout, and faith collided to shape his path to entrepreneurship, and why waiting to feel qualified can keep you from the exact opportunity you're meant for. Episode Highlights: Why readiness is overrated—and responsiveness is everythingHow Travis turned a single freelance gig into a full businessWhy your past jobs (even the weird ones) may be preparing youThe link between ministry, marketing, and meaningful workHow to overcome fear and imposter syndrome by building momentumAbout Travis: Travis Whatley is the founder of Holy Webs, a digital marketing agency helping small businesses grow through websites, SEO, and social media. Originally a youth pastor, he discovered his passion for marketing and turned it into a thriving business. With over 150 websites built, he is now expanding Holy Webs through the Local LeadersMarketers program and his book, "Count Me In." Focused on relationships and community impact, Travis is dedicated to helping businesses and ministry leaders succeed online. Holy Webs University: ARE YOU A MINISTRY LEADER? Build a Profitable Digital Marketing Business & Create Financial Freedom Imagine launching your own Holy Webs business for FREE, serving local businesses, and generating steady income—all without juggling a side gig that pulls you away from your ministry. Learn more at holywebsuniversity.com. Connect with Travis on Facebook Join the Christian Creative group on Skool. Learn more about 1:1 coaching or find tools to help with your jump to freelance at https://www.lunchtimeheroes.co/coaching.

    35 min
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Ratings & Reviews

5
out of 5
2 Ratings

About

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.

Information

  • Creator
    Matt Curtis
  • Years Active
    2024 - 2025
  • Episodes
    21
  • Rating
    Explicit
  • Copyright
    © 2025 The Jump Moment
  • Show Website
    The Jump Moment