A THREE-PART LEADERSHIP EXPERIENCE · SOUTH GEORGIAN BAY 2026
The Social
Enterprise
Journey
Equipping a Movement of Changemakers Across Ontario
Session 1 · Friday, May 22 · 9:00 AM – 12:00 PMSession 2 · Friday, June 19 · 9:00 AM – 2:00 PMSession 3 · Friday, September 11 · 9:00 AM – 12:00 PMCollingwood Library & Simcoe Street Theatre
PROUDLY SUPPORTED BY
ABOUT THE JOURNEY
Not a typical
workshop series.
Across Ontario, a powerful shift is underway. More business owners, founders, and leaders are asking how to build work that is financially sustainable while also strengthening their communities and ecosystems.
The Social Enterprise Journey is a curated, facilitated leadership experience combining systems thinking, social innovation tools, strategic planning with future foresight methodologies, and structured peer dialogue.
The series is led by Jessica Flynn, Social Innovation Fellow with Georgian College, and is supported by Georgian's mobile Community Impact Lab — bringing practical, hands-on tools directly into each session.
Mapping our Regions of Changemakers, February 2025. In collaboration with The Academy of South Georgian Bay, The Institute of Southern Georgian Bay, and Georgian College’s Social Innovation Department.“Strong, well-designed businesses are one of the most powerful drivers of lasting community impact.”
— Generation.org
Built for leaders doing meaningful work
Whether you are building a company, scaling a venture, or working in partnership with the business community, this series will help you think more strategically about the systems around you and your role within them.
WHO IS THIS FOR?
Business Owners & Founders
Local business owners and entrepreneurs ready to think strategically about their impact and long-term sustainability.
Municipal & Economic Development
Public sector leaders shaping the business ecosystem and community resilience strategies.
Social Enterprise Leaders
Leaders building ventures where financial sustainability and community impact are inseparable
Nonprofit Leaders
Nonprofit leaders who work closely with business ecosystems and want deeper strategic tools for sustainable, revenue-generating practices.
Consultants & Advisors
Professionals in the impact space who want stronger frameworks and a peer network.
Educators & Community Builders
People building systems and initiatives that strengthen communities from the ground up.
Three sessions.
One transformative arc.
Understanding the System
Every meaningful change effort begins with understanding the system we are working within. In this session, participants explore the deeper causes of the challenges they want to address and identify the key actors shaping the system. Arrive from 9:00 AM for coffee and light networking; session begins at 9:30.
Designing Your Impact Strategy
This expanded session explores how changemakers translate vision into strategy. We begin at Simcoe Street Theatre with a screening of Uncharitable — a film that challenges everything we think we know about how communities fund change. We then walk to the library for a working lunch and Theory of Change workshop. Arrive from 9:00 AM; film runs approx. 9:45–11:30 AM; Theory of Change begins 12:30 PM.
Activating Your Plan
In the final gathering, participants return with fresh perspective to refine their strategic direction. We review and strengthen each person's Theory of Change, explore the Flourishing Business Model framework for sustainable impact, and identify priorities and partnerships for the year ahead. You'll leave with a clear strategic roadmap for 2027 and beyond. Arrive from 9:00 AM for coffee and networking; session begins at 9:30.
INVESTMENT
Join the Journey.
All prices + HST. Registration includes full access to session materials and Georgian College's Community Impact Lab resources.
The Social Enterprise Journey is a three-part leadership experience designed for business owners, founders, and leaders who want to strengthen both the impact and sustainability of their work through revenue-generating ventures that also strengthen their communities.
Across Ontario, more leaders are asking:
How do we build businesses that are financially strong and meaningfully contribute to our communities?
This series brings together practical tools, strategic frameworks, and facilitated peer dialogue to help you step back, think clearly, and move forward with intention.
Led by Jessica Flynn (Social Innovation Fellow, Georgian College) and supported by Georgian’s mobile Community Impact Lab, this is not a typical workshop—it’s a guided strategic journey.
Additional Team Member tickets are available for $195 + HST each. Please email hello@thejessicaflynn.com to request a registration package for your entire team.
WHAT YOU’LL WALK AWAY WITH
✓ Identify the deeper systems behind the challenges you care about
✓ Clarify the change you want to create through your work
✓ Map the stakeholders and power dynamics shaping your work
✓ Develop a clear Theory of Change for your initiative
✓ Explore sustainable, revenue-aligned models for impact
✓ Leave ready to update your strategic plan for the year ahead
Real tools.
Renewed momentum.
This series applies social innovation tools through a business lens — helping participants strengthen their ventures, design more effective strategies, and build work that is both economically viable and meaningfully impactful.
Series FAQs
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The Social Enterprise Journey is a three-part leadership experience designed for business owners, founders, and leaders who want to build sustainable, revenue-generating ventures that also contribute meaningfully to their communities.
Each session builds on the last, guiding participants from understanding systems → to strategy → to activation.
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This series is designed for:
business owners and founders
consultants and advisors
social enterprise leaders
leaders building revenue-generating initiatives
While participants may come from multiple sectors, the experience is grounded in a business-first lens, focused on sustainability, strategy, and long-term impact.
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The series is designed as a complete journey, and participants will gain the most value by attending all three sessions.
Each session builds on the previous one, particularly through the development and refinement of your Theory of Change and strategic plan.
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That’s completely okay.
This series is not limited to formal social enterprises. It is for anyone building a business or initiative who wants to think more strategically about:
sustainability
impact
long-term value creation
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Your Journey Pass includes:
Access to all three sessions
Workshop materials and tools
Guided exercises and templates
Light refreshments (May & September)
Lunch during the June session
A curated group of peers and facilitated dialogue
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May & September: Collingwood Library (Third Floor)
June: Simcoe Street Theatre (morning) + Collingwood Library (afternoon)
Full details and reminders will be shared in advance of each session.
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May 22: 9:00 AM – 12:00 PM
June 19: 9:00 AM – 2:00 PM
September 11: 9:00 AM – 12:00 PM
Arrival begins at 9:00 AM (30 minutes before each session starts) for coffee and networking
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We understand that schedules can be complex.
All registered participants will receive access to a digital hub, where key materials—including canvases, tools, and tutorial guidance—will be available to support your learning and application if you need to miss a session.
Many participants also find value in:
sending a team member in their place
or reconnecting with others in the cohort to stay aligned
At this price point, the series is intentionally designed to deliver significant value even if you’re unable to attend every session live.
Our goal is for you to feel confident stepping into the full experience—knowing you’ll be supported every step of the way.
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Due to the limited capacity and curated nature of this experience, all registrations are non-refundable.
However, your ticket may be transferred to another attendee with a minimum of 48 hours’ business notice prior to the session.
Please contact us with the new participant’s details, and we’ll take care of the rest.
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Yes—and it’s encouraged.
We offer reduced pricing for additional team members, as attending together can help deepen learning and support implementation within your organization. Email hello@thejessicaflynn.com to request a registration package for your entire team.
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Yes.
Participants will be invited to explore additional opportunities for deeper support, including:
strategic advisory sessions
intensive workshops
future cohort or mastermind experiences
Copyright Georgian College’s Social Innovation Community Impact Network
THE FRAMEWORK
Grounded in
Social Innovation
The Social Enterprise Journey draws directly on the field of social innovation — developing new and more effective ways to address complex social and environmental challenges.
In this series, these tools are applied through a business lens, helping participants strengthen their ventures and design strategies that are both economically viable and meaningfully impactful.
Sessions are supported by Georgian College's Community Impact Lab — a mobile, hands-on toolkit bringing real social innovation methodology directly into the room.
YOUR FACILITATOR
Jessica Flynn
Georgian College Social Innovation Fellow · Founder & Principal Consultant · Series Facilitator
Jessica Flynn is an educator, strategist, and facilitator who works with leaders across business, nonprofit, and education sectors to strengthen collaboration and unlock new possibilities for impact.
Her work spans youth entrepreneurship, social innovation, and community ecosystem development. She is the founder of The YOU Power Project, Social Innovation Fellow at Georgian College, and a trusted advisor to organizations seeking to align purpose with sustainable strategy.
Jessica is known for creating thoughtful spaces where leaders can step back, see the bigger picture, and move forward with clarity.
Systems Thinking
Social Innovation
Strategic Facilitation
Community Ecosystems
Youth Empowerment
SERIES SPONSORS & COLLABORATORS
Backed by trusted institutions.
The Social Enterprise Journey is proudly supported by organizations committed to strengthening business leadership and community impact across Ontario.
Ready to join the Journey?
Three sessions. A growing network of changemakers. Practical tools you'll use immediately.
Space is limited — secure your place today.
All prices + HST · Collingwood, Ontario · May – September 2026