Episode 38: How to Learn Freelancing with Matthew Dowling

Episode 38: How to Learn Freelancing with Matthew Dowling

Author: Sarah Duran January 30, 2025 Duration: 39:36

Matt Dowling is the founder of Freelancer Club, a platform born from his personal battle with an unpaid invoice that gained national attention. Freelancer Club equips over 72,000 freelancers with the tools, skills, and connections to thrive professionally.

In this episode, Matt shares the evolution of Freelancer Club from a Facebook support group to a comprehensive platform that combines education, community, and policy advocacy.

His journey shows how personal setbacks can fuel systemic change. His campaigns, including #NOFREEWORK and ‘Rise, Freelancer,’ have championed fair pay, diversity, and inclusion, aiming to support 1 million freelancers by 2026.

Our conversation also explores the changing landscape of freelance work, particularly how younger generations view independent work as less risky than traditional employment. We discuss Freelancer Club's innovative approach to education, teaching business skills by tapping into people's natural entrepreneurial instincts, and their work on policy reform to create better protections for independent workers.

Whether you're an aspiring freelancer, an educator interested in preparing students for the future of work, or someone passionate about freelancer rights, Matt's insights into building a more equitable and supportive freelance ecosystem offer valuable perspective on where independent work is headed.

Learn more about Matt and Freelancer Club on LinkedIn, his website, Spotify, or Apple Podcasts.

For more content and live events go to www.fruitioninitiatives.com.


Hosted by Sarah Duran, The Future is Freelance moves beyond the typical success story narrative to tackle the real, often unspoken, challenges of independent work. This podcast operates on a core belief: the most practical and resilient solutions are forged by the people living this reality every day. Each episode convenes voices from across the entire freelance ecosystem-from solo creators and agency owners to platform developers and policy advocates. The goal is to break down the silos and echo chambers that often isolate us, creating a rare space for genuine dialogue. You’ll hear frank discussions about pricing, client relationships, systemic inequities, mental health, and the philosophical shifts redefining modern work. Rather than offering one-size-fits-all advice, these conversations leverage collective wisdom to explore actionable paths forward. Tuning in means joining a grounded community effort to not just navigate the present landscape, but to actively shape what comes next. It’s for anyone curious about the human and structural dynamics behind the growing freelance economy, seeking both solidarity and substantive strategy.
Author: Language: English Episodes: 72

The Future is Freelance
Podcast Episodes
Episode 9: Online Learning Content with Chris Badgett [not-audio_url] [/not-audio_url]

Duration: 30:07
Chris has a super interesting entrepreneurial journey that led him to his current work, where he helps to make sharing expertise more accessible online and level the playing field in DIY education. Chris Badgett is the c…
Episode 8: Holding Yourself Accountable with Tim Melanson [not-audio_url] [/not-audio_url]

Duration: 35:36
I was on Tim Melanson's podcast last year and immediately knew that we shared the same mission to help others make the most of independent, flexible work. Tim is the Host of the Work at Home RockStar Podcast, a Self-Impr…
Episode 7: Breaking Glass Ceilings with Rachel Everington [not-audio_url] [/not-audio_url]

Duration: 45:20
The first time I talked to Rachel, I knew she was a hustler at heart - paving her own way, breaking glass ceilings, and helping others build strong independent businesses is her jam. Rachel is the CEO of an executive ass…
Episode 6: Following Your Dreams with Andrea Sager [not-audio_url] [/not-audio_url]

Duration: 38:19
Andrea Sager is no stranger to solopreneurship. After landing what she thought was her dream job, she realized that she wanted more. I had a great time chatting with Andrea about following your dreams no matter what (plu…
Episode 5: Doing What You Love with Shiela Pialago [not-audio_url] [/not-audio_url]

Duration: 32:45
Shiela and I hit it off when I was on her podcast and never looked back. She's a multi-talented freelancer who loves what she does and sharing it with others. Shiela is a skilled Digital Project Manager and Growth Market…
Episode 4: Working Better with Anna Burgess Yang [not-audio_url] [/not-audio_url]

Duration: 33:54
My good friend Anna always makes me think differently about work, productivity, and efficiency.Anna is a former product manager who left an executive role in 2021 to pursue an entirely different life. After bouncing arou…
Episode 2: The Power of Genuine Connections with Corey Fradin [not-audio_url] [/not-audio_url]

Duration: 31:10
Corey is one of the most genuine people I have ever met and I'm so excited to have him on the podcast. Corey is the cofounder @ Authrs.io - an agency that ghostwrites, markets, and publishes best-selling books for busy p…
Episode 1: The Relentless Pursuit of Freedom with Molly Rose Speed [not-audio_url] [/not-audio_url]

Duration: 22:17
I'm thrilled to chat with Molly Rose Speed for our first episode of the new podcast! We talk about all things freedom and how to do what only you can do by delegating and outsourcing. Molly is an expert in creating what…