The Future is Freelance

Hosted by Sarah Duran

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Feb 2025

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February 13, 202531 min

Episode 39: Work That Matters with Joel Sousa

Joel Sousa is a brand strategist and designer who helps solopreneurs stand out as experts. After a decade of freelancing, Joel made a bold pivot in 2020 - firing all his corporate clients to focus exclusively on serving independent business owners. In this episode, Joel shares his journey from working with large corporations to finding fulfillment helping fellow solopreneurs build authentic brands. We chat about how success metrics in business often get reduced to oversimplified soundbites about money and time, when true success is deeply personal. Our conversation also goes into why money alone can't sustain independent businesses, how saying "no" can lead to more revenue, and the importance of aligning your work with your values for both business and life satisfaction. Whether you're considering a business pivot or feeling stuck in work that looks successful but feels unfulfilling, Joel's insights offer a fresh perspective on creating a business that truly works for you. Learn more about Joel on LinkedIn, Instagram, or https://growingdesign.pt/ . For more content and live events go to http://www.fruitioninitiatives.com/

January 30, 202539 min

Episode 38: How to Learn Freelancing with Matthew Dowling

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.

January 16, 202527 min

Episode 37: The Power of No with Natalie Serkin

Natalie Serkin is the President & Co-Founder of Collective IQ and brings over 20 years of experience in art direction, production, and studio management to her role leading creative product and process design. Throughout her career, she has led studio and design departments at several major agencies, including restructuring 13 different agencies, before founding her own company built on the principles of honesty and integrity in client relationships. In this episode, Natalie shares how her reputation for being "too honest" with clients - once considered a liability in the agency world - became the foundation for building Collective IQ. Her journey from creative director to agency founder challenges traditional agency models that prioritize service over results, offering a fresh perspective on how transparency and authentic relationships lead to better creative work. We discuss the power of strategic "nos," building an agency that never compromises the work or the people, and how the marketing industry has evolved to demand more honesty and authentic partnerships. Natalie's approach to scaling a creative services business while maintaining high standards of integrity offers valuable insights for freelancers considering growth and independent professionals navigating client relationships. Whether you're a solo creative considering scaling your business, or an independent professional looking to build stronger client partnerships, Natalie's practical wisdom about building success through honesty and expertise offers valuable insights for anyone in the creative services industry. Learn more about Natalie at https://www.coiq.com/ For more content and live events go to https://www.fruitioninitiatives.com

January 2, 202548 min

Episode 18: How to Plan for the New Year with Anna Burgess Yang

We're bringing back Anna Burgess Yang to help us think about how to plan for the new year as a freelancer! Anna is a former product manager who left an executive role in 2021 to pursue an entirely different life. After bouncing around a few different jobs for two years, Anna is now a freelance technology writer and journalist. She is also obsessed with workflow automation and removing boring/tedious work from life. She helps freelancers and other solopreneurs do the same through written how-to guides and 1:1 workflow consulting. She lives in a suburb of Chicago with her husband, three kids, and three cats. In addition to client work, she writes on Medium, Substack, and has a newsletter. To learn more about Anna, visit both of her websites https://www.annabyang.com/ and https://www.tinkeringwithideas.io/ and check out her writing at https://annabyang.substack.com/. To learn more about Sarah, go to https://www.fruitioninitiatives.com.

December 12, 202423 min

Episode 36: Community Powered Platforms with Amy Choi

Amy Choi is the co-founder of WorkFree, the first freelance platform powered by communities. As a former freelancer and global professional with 15+ years of experience across tech sales, recruitment, and digital marketing, Amy understands firsthand the challenges and opportunities in the freelance ecosystem. In this episode, Amy shares how her transition to freelancing after becoming a mother led to creating WorkFree, a unique three-sided marketplace connecting freelance communities, talent, and clients. Our conversation explores the innovative approach of putting communities at the center of freelance work, recognizing and formalizing the organic networks that freelancers have always used to find work and support each other. We discuss the intentional design decisions behind WorkFree's platform, the importance of creating win-win-win scenarios for all participants, and how understanding the freelance experience firsthand leads to more thoughtful, effective solutions for the independent workforce. Whether you're a freelancer, community leader, or company looking to build stronger relationships with independent talent, Amy's practical wisdom and innovative approach offer valuable insights into the future of freelance work. Learn more about Amy on her website or LinkedIn For more content and live events go to www.fruitioninitiatives.com

November 14, 202431 min

Episode 35: Independent Consultants with Melisa Liberman

Melisa Liberman is a business coach for independent consultants and author of "Grow Your Consulting Business: The 14-Step Roadmap to Make Your Independent Consulting Goals a Reality." In this episode, she shares her journey from corporate executive to accidental entrepreneur, offering deep insights into the mindset shifts required when transitioning from corporate to independent work. Her story is particularly compelling because it highlights a common experience among consultants: the unexpected challenge of rebuilding identity and confidence outside the corporate structure. Our conversation explores the nuanced differences between freelancers, consultants, and other independent workers, but more importantly, dives into the psychological aspects of this career transition. Even professionals with impressive credentials and extensive experience face imposter syndrome and self-doubt when striking out on their own. Melisa's candid discussion about her own journey from being labeled "sales repellent" in her corporate role to successfully running her own business provides valuable insights for anyone considering or currently navigating the independent path. We also discuss the critical mindset shifts required for success - from embracing failure as a learning opportunity to developing a business owner's perspective. The conversation reveals how the transition from corporate to independent work isn't just about changing how you work, but fundamentally transforming how you think about yourself and your value in the marketplace. Whether you're considering the leap to independent consulting or already running your own practice, Melisa's practical wisdom and honest insights about the realities of building a consulting business offer valuable guidance for creating a sustainable independent career. Learn more about Melisa: Grow Your Consulting Business: The 14-Step Roadmap to Make Your Independent Consulting Goals a Reality Grow Your Independent Consulting Business Podcast  LinkedIn   For more content and live events go to www.fruitioninitiatives.com.

October 24, 202440 min

Episode 34: Working with Friends with Rachel Renock

Rachel Renock has been an incredible innovator in the freelance space, and this conversation barely scratches the surface of her expertise in helping independents build more profitable and collaborative businesses. In this episode, we dive deep into the future of freelance work, exploring what Rachel calls "virtual studios" - a model where freelancers team up fluidly to tackle bigger projects and scale their businesses without the traditional overhead of agencies. Drawing from her experience as both a former advertising creative and now the CEO of Wethos, Rachel shares invaluable insights on: The power of collaborative freelancing and building "elastic" businesses Why transparency in pricing is crucial for the entire freelance ecosystem How to think about scaling a service-based business without falling into common traps The importance of focusing on profitability over productivity How crowdsourced data can help freelancers command better rates  Whether you're a solo freelancer looking to grow your business or someone interested in the future of work, Rachel's perspective on building more sustainable and profitable independent businesses is a must-listen. Learn more about Rachel. For more content and live events go to https://www.fruitioninitiatives.com

October 10, 202437 min

Episode 33: The Democratization of Work with Steve King

It was a pleasure having Steve King, a founding partner of Emergent Research, on the podcast. With over 25 years of experience, his work focuses on the future of work, particularly how it impacts small businesses, independent workers, and the gig economy. Our conversation covers a range of topics, including the post-pandemic rise in full-time freelancing, the impact of AI on independent work, and the changing perceptions of freelancing in academia and business. Steve offers unique insights as both a researcher and a practitioner, running Emergent Research as a two-person operation that leverages freelance talent. We discuss the importance of understanding risk profiles for freelancers, the need for better systems to connect independent workers with clients, and the exciting opportunities that new technologies bring to the freelance world. Whether you're an independent professional or a company leader, this episode provides valuable insights into the trends shaping the future of work. To learn more about Steve go to www.emergentresearch.com or his LinkedIn. For more content and live events go to www.fruitioninitiatives.com.

September 26, 202443 min

Episode 32: The Future is Freelance with Matthew Mottola

Matthew has been an invaluable thought leader in the freelance ecosystem, and this conversation barely scratches the surface of his deep expertise in the future of work and the freelance economy. We dive into some fascinating topics that are crucial for both freelancers and the companies that hire them like:  The "Expert's Curse" in consulting and how it affects freelancers transitioning from corporate roles - Whether the freelance economy is truly a revolution or more of an evolution The challenges companies face in scaling freelance programs and how we can address them The power (and pitfalls) of terminology in our industry - from "gig work" to "consulting" to "fractional" How the future of work is shaping up and what it means for both independent professionals and traditional businesses Whether you're a solo consultant aiming to build a sustainable business or a company leader interested in leveraging freelance talent more effectively, this episode offers valuable insights that will help you navigate the changing landscape of work. To learn more about Matthew:  Follow Human CloudFollow on LinkedInFollow Human Cloud on LinkedInListen to the Human Cloud PodcastBuy the Human Cloud Book For more content and live events go to www.fruitioninitiatives.com.

September 12, 202436 min

Episode 31: The Consultant Blueprint with Laura Burford

Laura has been an amazing thought partner and this conversation is just the tip of the iceberg in terms of her deep expertise helping independent consultants build sustainable businesses. In this episode we talk about her consultant blueprint, becoming an accidental entrepreneur, and the future of work. To learn more about Laura, go to her website, LinkedIn, Youtube, or Medium. To learn more about Sarah, go to www.fruitioninitiatives.com. For early access and transcriptions, subscribe at www.thehustlersmanifesto.com