make the jump to freelance
Jump to Freelance gives you the inspiration, tools, and community to make the jump to freelance with confidence—and thrive on the other side.
Prepare for your jump
The Jump Moment Podcast
The Jump Moment uncovers the exact moment when creatives and entrepreneurs decided to make the jump into starting their own thing. Through their stories, you’ll gain insight, learn valuable lessons, and find the inspiration to take your own jump with confidence.
Jump to Freelance Community
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.
Coaching built for your business
Enough with the one-size-fits-all frameworks! My one to one coaching is all about your business. Together, we’ll build a plan tailored to your goals, challenges, and creative strengths—so you’ll know exactly what to do next to move your business forward with confidence.
Freelance can feel scary
The fear of making the jump to freelance is one of the biggest reasons creatives like you stay where you are instead of starting your own thing.
That fear isn’t all bad.
You’ll face real challenges when you start a business. But every one of those challenges can be overcome.
In 2017, I decided to stop dreaming about freelancing and start building. I launched Deacon Coffee Co., a backyard coffee roasting business with a mission to educate customers on the culture and history of coffee.
This was the season I moved past “I’m creative but don’t know business” and learned what it took to start something real. I knew coffee roasting wouldn’t be my full-time career, but it laid the foundation for what I needed a few years later.
One of the biggest lessons I learned during that time was how critical inspiration is to staying motivated. Podcasts became my fuel—hearing business owners share their stories, lessons, and wisdom gave me the push I needed to keep going.
That’s exactly why I created The Jump Moment.
Listening to the stories of those further along than me turned my fear into inspiration. I hope this podcast does the same for you.
Everyone has a jump moment
My Jump Moment happened in 2022. My wife had medical needs that the insurance from my job wouldn’t cover. We found out just in time to enroll in a plan through our state’s insurance marketplace.
It didn’t feel like a “jump moment” at all—it felt like a push. But because I’d spent years learning and experimenting with side ventures, I was ready.
Well, sort of. While I had knowledge, I wasn’t exactly sure what the best first steps were to building my business. That’s when I leaned into networking and met someone who would become my mentor, Barbara Carneiro.
Barbara mentored me as I built my business, Lunchtime Heroes. Through her mentorship, I connected with other business leaders serving the same audience, and I realized how powerful community truly is.
I’m not going to sugarcoat it: freelancing is hard. It’s fulfilling, stressful, rewarding, and challenging all at once—and it’s even harder when you’re trying to do it alone.
That’s why I built the Jump to Freelance community on Skool. It’s designed for creatives serious about freelancing—whether you’re building a side hustle alongside a job you love or aspiring to something much bigger, community is key.
If you’re in more of a “push moment” and building fast is a priority, I offer one to one coaching to help you create a focused plan tailored to your goals.
Freelancing isn’t for everyone. But if it’s for you, I’d love to help you prepare for your jump.
Hi, I’m Matt!
I know firsthand how daunting freelancing can feel. After 20 years as a creative, dreaming of running my own business, I finally made the jump to freelance in 2022—and I haven’t looked back.
Over the past few years, I’ve heard from more and more creatives who want to make the jump but don’t know where to start. That’s why I created Jump to Freelance.
I’ve been where you are—feeling stuck in a place that isn’t life-giving, yet unsure of what to do next. Now, having experienced what’s possible on the other side, I’m here to help other creatives make their jump to freelance with confidence.
Whether you’re just starting to dream, actively planning, or building momentum after making the jump, I’ll help you navigate the adventure of creative freelance.