Toronto to Tiny: Reflections from Our First Ontario Retreat

Centre Beach, Tiny, Ontario

Every year, our team gathers for a retreat to slow down, reconnect, and think together about where we're headed and how we can support each other in our shared work. As our team has spread across the country from Vancouver to Waterloo, Halifax, and Montreal, we wanted our retreat to reflect how these regional roots can grow into national impact. So this year, for the first time, we gathered in Ontario for a five day adventure that took us from downtown Toronto to Tiny on the shores of Georgian Bay.

Day 1: Grounding in Our Mission

At the Centre for Social Innovation, we kicked off the retreat by grounding into our BHAG (big hairy audacious goal): a social purpose sector that is respected, resourced, and resilient. From there, we talked about our specific role in achieving that goal. We see ourselves as a "level-up" partner to the sector, helping make its work more visible, and building capacity from the inside out through community-grounded projects supported by facilitators with deep regional knowledge.

We structured the rest of the week around our 2026-2030 strategic priorities, giving each one dedicated space and time to reflect on what we've tried, what we've learned, and where we still have questions.

Day 2: From Excellent Services to Trusted Partners

Much of our week was spent reflecting on what it means to be a trusted partner to the organizations we work with. We talked through what that could look like in practice. What does it look like to stay involved after a strategic plan is delivered? How do we support organizations build their own capacity to carry the work forward rather than creating dependence on us? This transition from a time-bound engagement to a long term commitment is a meaningful shift in how we think about our work.

Day 3: From Individual Talent to Collective Ecosystem

The most important ingredient in our ability to deliver relational, community-grounded services from coast to coast is a staff team and ecosystem members that are deeply connected to the communities where they live. There is no short cut to building relationships with great strategists, evaluators, and facilitators across the country which is part of why we continue to invest in it as we grow.

We got active with that relational work during a gathering we hosted for our Greater Toronto and Hamilton-based community, collaborators, and clients at YWCA Toronto. We were excited to spend the evening with a great mix of people we already work with and others that we hope to.

Our aim was to connect with values-aligned people and sow seeds for future collaboration. Though many arrived not knowing each other, we saw how having a common connection to Roots & Rivers created a special openness to the way people interacted with each other. We heard that people didn't feel “evaluated” in the same way they might at “traditional” networking events and know that some great, sustained connections were made. We also heard from attendees how much they'd missed simply being in a room with other people doing similar work after so much time working from home.

Our team left the event feeling energized and grateful, and with a picture of what we're still figuring out. As we try to grow something closer to a community of practice, we know that in-person and virtual spaces for connection, peer exchange, and collective care strengthen our national network of social purpose consultants. We're still learning how to make our network accessible and sustainable.

Day 4: From Emerging Practice to Resilient Organization

We spent time on the internal work of becoming a more resilient organization. This less visible work includes practical considerations like how we document what we do, how we make our own systems easier to use and maintain, and high-level questions like how we hold onto what makes our approach distinctly ours as we take on new kinds of work.

Day 5: Regional Roots, National Impact

Hosting our retreat and gathering with our community in Ontario for the first time prompted a lot of reflection. We talked about what it has meant to show up in new-to-us communities through events and connections with local practitioners. Part of realizing our ambition to have national impact is sharing what we're learning, through the work itself and the conversations it sparks.

Closing with Our Values

We ended the retreat by naming which of our values showed up strongest during our time together. Love and courage stood out: love for the work and for each other, and courage to be honest, to be vulnerable, and to sit with the questions. Respect for the foundations we've built, for different perspectives and ways of being, and for each other as full people, not just colleagues on a screen, came up too. Patience over urgency was the value we agreed we most want to lean into as we keep growing.

What We're Taking Forward

As an entirely remote team, simply getting to see and know each other in three dimensions is important in ways that are hard to fully articulate. We were reminded that a retreat doesn't need to solve everything to be worthwhile. Sometimes the value is in the gathering itself. What we left with was a stronger sense of what a coast-to-coast Roots & Rivers actually looks like, and a renewed commitment to building it with patience, alongside the people and communities we're lucky to work with.