The Future is Freelance
A collaborative event series for stakeholders from all levels of the freelance ecosystem.
Next Forum:
The Other Work: What happens when you stop working in your business long enough to work on it
Featured guests
Caitlyn Tivy, freelance clinical consultant
Maari Casey, founder of Uncompany
Lizzie Davey, freelance writer and founder of Freelance Magic
April 21, 2026, 9am MST
The Future of Freelance Forums are a series of collaborative events designed to surface and solve the problems we all face as independent workers and those who support them.
Each topical discussion will feature a curated group of speakers,
but this isn’t a panel of “experts” giving solutions; it is a collaborative conversation where we design solutions together.
Join our next collaborative conversation: The Other Work: What happens when you stop working in your business long enough to work on it
Where we'll explore the following questions:
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What does "working on your business" actually mean to you?
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What has to be true for this kind of work to feel possible?
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What have you learned about your business in those moments when you've had the space to look at it clearly?
Who is it for?
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Freelancers
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Coaches and content creators who support freelancers
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Community and advocacy leaders
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Platform and agency founders
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Tool and solution creators
Where does it happen?
All current sessions will happen on Zoom, but we hope to launch some in-person events soon.
What’s it like?
This is a completely unique experience—think part panel, part workshop, part Q&A. This is not a “sit-and-get” webinar where you chill with your camera off while you check your email. Be prepared to contribute, interact in breakout groups, and share your best thinking.
How do I sign up?
Click the button below.
Meet our featured guests
Caitlyn Tivy is a freelance clinical consultant who has built regular business retreats into the rhythm of her work; not as a luxury, but as a practice. She knows firsthand what it takes to carve out intentional space when client work always feels more urgent, and she brings a grounded, practical perspective on what it actually looks like to protect time for the business behind the business.
Maari Casey is the founder of Uncompany, a freelance collective built on the belief that freelancers deserve a real operating system, not just gigs. A former ad agency art director, Maari spent over a decade as a freelancer before launching Uncompany to solve the problems she lived herself: how to build a sustainable business, connect with the right clients, and design a life where work plays a supporting role. Her mission is making unconventional working more workable.
Lizzie Davey is a freelance writer for brands like Shopify, Klaviyo, and CoSchedule, and the founder of Freelance Magic. Based in Brighton, she's spent over a decade building a business that works on her terms and now helps other freelancers do the same through her newsletter, podcast (It's Fine, I'm a Freelancer), and mentoring. She's one of the sharper voices in the freelance space on what it takes to build something sustainable, not just survive client to client.
What People Are Saying
"It's my favorite online meetup for freelancers all over the world, and Sarah, thank you a ton for bringing us all together, and creating this safe, trusted space where we can be our true selves."
~ Yurii, forum participant
"Different perspectives, great thought-provoking questions. Brilliant facilitation. Lovely group of people."
~ Una, forum participant
"I love the opportunity to connect with experienced freelancers, very enlightening."
~ Kayla, forum participant
"I always love the thought-provoking and strategic questions you ask, as well as the wisdom of what's working for others here."
~ Colleen, forum participant
Hi, I'm Sarah.
Your host and moderator.
I'm an independent COO who helps solo business owners scale on their own terms.
Through my work as a coach, content creator, and thought leader, I’ve met hundreds of amazing people who are working toward a future where independent work is valued.
Every time I make a connection, I wonder how we can work more effectively together toward our shared goals. The Future is Freelance Forums are the first step toward a broader coalition of leaders working toward the future of work.
I believe the best solutions come from the ground-up, from people with skin in the game, but often we operate in silos and echo chambers instead of leveraging the power of the collective.
The Future is Freelance Forums honors the expertise that comes from all levels of the freelance ecosystem, from freelancer to platform CEO, from community builder to enterprise leader.
My facilitation style cultivates this innate expertise in each participant to bring forward the most innovative solutions that benefit everyone.
"Sarah is not only deeply committed to the freelance economy, but she is also THE expert when it comes to helping independent professionals build sustainable, fulfilling, and profitable careers.
If I had to choose one person to lead the charge on the freelance revolution, it would be Sarah."
Úna Herlihy
Co-founder of The Indie List
“Sarah is one of the brightest voices in the business of freelancing.”
Robert Vlach
Best-Selling Author of The Freelance Way and Founder of Freelancing.eu
"You learn how to spot the authentic leaders from the bluffers - the ones whose company statement isn’t just a smokescreen to charge a premium but a genuine commitment to making a difference.
Sarah is one such champion. Passionate, insightful and with a clear sense of purpose."
Matthew Dowling
Founder of Freelancer Club
"Sarah is our go-to for EVERYTHING freelancer-related in our incredible industry."
Matthew Mottola
CEO of The Human Cloud
The future of work will be defined by those who freelance and those who build the infrastructure to support them.
Thousands of people, platforms, and programs are pushing the world to embrace and respect independent work.
What would it look like if we came together to solve the biggest problems facing the freelance ecosystem instead of in isolation?
Freelancers
How might your work look different if you could thought-partner with the leaders building the communities, platforms, tools, and solutions you rely on every day?
Coaches
How might your programs look different if you could dig deep with a dedicated group of freelancers, platform pioneers, and thought leaders on the biggest problems facing freelancers?
Community and advocacy leaders
How might the impact of your work change if you could leverage the collective power of a dedicated group of like-minded peers?
Platform and tool innovators
How might the effectiveness and adoption of your solutions change if you could tailor them to the specific needs of not just individual freelancers but the broader freelance ecosystem?
We’re all working on the same problems; let’s get better at finding the solutions together.
Resources from Past Forums
The Referral Engine: Creating Referral Relationships That Work for Everyone
Featured guests
Reuben Swartz, Founder of Mimiran
Úna Herlihy, Co-founder of The Indie List
Questions we explored:
- When have referrals felt natural and easy, versus forced or awkward?
- What's stopping you from consistently giving or getting referrals in your business right now?
- What are the systematic approaches we need to take to make and get the right connections?
Summary coming soon!
Business pivots: The when, why, and how
Featured guests
Jessica Walrack Freelance finance writer and founder of All Things Freelance Writing
Liz Heflin Freelance writer, founder of Heflin Media Group
Joel Sousa Brand strategist and designer for solopreneurs at GrowingDesign
Questions we explored:
- When do you know it's time to pivot?
- Why is it so hard to pivot?
- How do you pivot without losing everything you've built?
How to take long-term leave as a freelancer
Featured guests
Anna Burgess Yang, Solopreneur Operations
Helen Dibble, Managing Director, incredibble
Lucy Werner, Founder of Hype Yourself Network
Questions we explored:
- What are the myths around taking long-term leave as a freelancer?
- How do we need to change our mindset, and the mindsets of our clients, to make this possible?
- What are the logistical implications of taking leave?
Business Strategy for Freelancers
Featured guests
Elina Jutelyte, Founder of Freelance Business Community
Laura Burford, Strategic Advisor for Independent Consultants
Questions we explored:
- What IS business strategy?
- How is the strategy for freelance businesses different?
- How can freelance business owners set the right goals and actually achieve them?
The Tools Freelancers Need to Run a Business of One
Featured guests
Rachel Renock, Product & Growth Strategist | Former Cofounder @ Wethos (acquired)
Ben Gallagher, Customer Success Manager at Full Scope
Questions we explored:
- What types of tools does your tech stack include?
- What are the limitations of the tools you use?
- What are the structural implications for your business?
Building Your Reputation as a Freelancer
Featured guests
Joel Sousa, Brand Strategist
Yurii Lazaruk, Go-To-Market Community Expert
Emily Who Explores, Outdoor Content Marketer & Creator
Questions we explored:
- Do freelancers need a "personal brand"?
- How do freelancers build their authority and reputation?
How Can We Prepare the Next Generation of Freelancers?
Featured guests
Matt Dowling, Founder, Freelancer Club
Eryn Peters, Marketplace Nerd, Startup Advisor, Editor of Weekly Workforce
Rafael Espinal, Executive Director, Freelancers Union
Elliot Williams, Strategic Storyteller
Questions we explored:
- How does one “learn” how to freelance?
- What are the conditions that allow the next generation of freelancers to thrive?
- How can the global economy prepare for the continued rise of flexible talent?
Collectives As Agencies of the Future
Featured guests
Rachel Renock, Cofounder & CEO of Wethos
Hollie Fraser, Founder of We Are Shelance
Matthew Knight, Chief Freelance Officer at Outside Perspective
Questions we explored:
- Why do freelancers form and join collectives, collaboratives, and communities?
- What are the criteria for effective collectives, collaboratives, and communities?
- How do these organizations serve as “agencies of the future” in helping match clients and freelancers?
How to Find Clients: Platforms, Networking, LinkedIn and Everything In-between
Featured guests
Lizzie Davey, B2B SaaS + Ecommerce Writer
Reuben Swartz, Founder of Mimiran, the Anti-CRM
Jonathan Eadie, Co-founder of Shoutt
Questions we explored:
- What are the pros and cons to the various methods of finding clients?
- Which methods lend themselves to specific types of freelancers, services, deliverables, and offerings?
- How can the freelance ecosystem better connect freelancers with clients and vice versa?
Why Enterprise Companies and Freelancers Need Each Other
Featured guests
Matthew Mottola, CEO of The Human Cloud
Laura Gil Alcalde, Freelance Program Manager
Riley Kaminer, Content Strategist, Founder of ClearCritical
Questions we explored:
- What are the barriers to flexible workforce adoption for larger enterprise companies?
- What are the barriers for freelancers to finding work with larger companies?
- How can the freelance ecosystem work to address this divide to ensure the growth of the freelance economy?
The Pricing Paradox
Featured guests
Robert Vlach, Best-Selling Author of The Freelance Way and Founder of Freelancing.eu
Rachel Renock, Cofounder & CEO of Wethos
Lizzie Davey, B2B SaaS + Ecommerce Writer
Questions we explored:
- What are the pricing structures and strategies that lead to long-term success?
- How do freelance businesses consider pricing a mechanism for freedom and fulfillment?
- How can the freelance ecosystem (coaches, community leaders, platforms) create infrastructure to foster better pay, close income gaps, and increase transparency?
What Makes a Freelance Business Sustainable?
Featured guests
Elina Jutelyte, Founder of The Freelance Business Community
Anna Burgess Yang, Solopreneur Operations
Maari Casey, CEO of Uncompany
Questions we explored:
- What are the criteria for a sustainable freelance business?
- How can the freelance ecosystem (coaches, community leaders, platforms) help to foster conditions that lead to sustainability?
- What are the barriers to sustainability at all levels of the freelance ecosystem, and how can we address them?