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Wayside Journey

Wayside Journey by Tyler Colbourne

At Inspiring Communities we often like to call ourselves a learning organization. Well, over the last 12 months I have certainly learned a lot. 

I became Community Director at Inspiring Communities in the Fall of 2020. I had just completed my degree and after 18 years of trying, I finally felt like my education and knowledge, values, and skills were in alignment. In my new role I was tasked with supporting and acting as the main point of contact for our Collective Impact sites and network building initiatives. As an organization, we were exploring different models and formats for accountability and empowerment of staff. We had hoped that this iteration and format would allow for closer collaboration and support for the nested initiatives at Inspiring Communities. However, I was only in this role for two months when everything changed. 

In 2020, our previous Executive Director moved on after five amazing years stewarding this organization. We as a leadership team asked ourselves, “where did we have capacity and who was best suited to hold tasks and responsibilities within our team?” Inspiring Communities had recently acquired Wayside, a charitable organization with the mandate of providing online educational experiences and community for changemakers in Atlantic Canada. Inspiring Communities, as so many for-impact organizations, can be big on vision and opportunity and sometimes we don’t have the capacity or resources to fully realize that vision. 

After we considered our assets within our backbone team and the resources we had available, my roles and responsibilities shifted greatly. I took on the leadership role for communications and internal and external learning at our organization, including leading our Wayside Online Community. I had some experience launching and re-envisioning an online Learning Management System (LMS) at other non-profits and I have plenty of experience in communications and network building. 

However, I will be honest in saying that I wasn’t sure what I was getting myself into. 


When my role shifted there were four of us on the team, with our work touching WeavEast, Wayside, and communications. From the moment my role shifted, I knew that for this to be at all successful, we needed to focus on the people who were on this team. Each of us had roles and responsibilities that contributed to many other areas of work, but what connected us was WeavEast and Wayside.

WeavEast, a three-year initiative funded by the McConnell Foundation, was seemingly a perfect fit. That project aimed to support changemakers and social innovators throughout Atlantic Canada and our hope was that we could bridge Wayside with WeavEast. 

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At this time the vision for Wayside was amorphous, shifting often, and I didn’t have a clear understanding of how the platform and community would contribute to the work of Inspiring Communities (although our Online Animator had a great grasp of how the technology should evolve). Our team, however, knew we had the opportunity to build something great amongst us. Early on, we adopted a mindset of experimentation while making room for failure. In our first week together as a team, Miranda Cobb, Evaluation & Research Lead with WeavEast and Wayside facilitated an intriguing activity: How Can We Reliably Tank Wayside? This activity encouraged us to explore all the ways (from realistic and possible to ridiculous and unbelievable) we could tank, annihilate, and ruin Wayside–a roundabout way of identifying critical success factors. This exercise showed us that to be successful we would need to: 

  • Consider the fundamentals. Our office didn’t have reliable internet, so how could we launch an online learning platform? 
  • Need to believe in ourselves while also holding space for being critical. 
  • Consult and include those who came before and those who have yet to come. There were many people in the ecosystem of Wayside, and we needed to get a sense of what their hopes and aspirations were. We also needed to commit to seeing Wayside as a part of Inspiring Communities, even if we didn’t fully know what that meant. 
  • Make a plan. We especially needed processes for how we built relationships internally and externally. This plan needed to include how we might explore revenue generation. 
  • Cultivate and curate the platform so that it nurtures the community. This meant we needed to be responsive and shift our plans as we learned new information and built new partnerships. 
  • Find a way to make Wayside the best part of our work.
  • Understand that our team wasn’t just in service of the changemakers we were hoping to support. We too were these changemakers and we needed to start by supporting each other. 
  • Be comfortable with failure

In reflecting on these priorities, I believe we achieved all of these things. We created a team of Wayside Wonders, composed of Charlene Boyce, Content Curator; Olu Osunrinde, Online Animator; Miranda Cobb, Evaluation Lead, and myself, Tyler Colbourne, Community Director. We certainly took on too much, but we learned a lot. My role shifted over time, allowing me to dedicate myself more fully to Wayside and WeavEast, while distributing parts of my role across the leadership team. We took on too much, and the Wayside Wonders did wonderful things. 

I am most proud of how we built a team founded on candour, compassion, equity, and humility. Our deep and meaningful conversations were supported and scaffolded by our ridiculous and whimsical ones. We had beautiful capes, we laughed, we did our best to plan retreats that kept getting postponed due to COVID-19, and we approached new challenges with critical thinking and optimism. I believe each of us stepped into our collaborations and individual work with humility and grace, while also being sure to communicate what wasn’t working for us and celebrating our wins. I can confidently say that working with and leading this team has been the best part of my work over the last 2.5 years at Inspiring Communities. 

We built amazing relationships with instructors and partners, we had a lot of fun as a team, and we learned a lot about ourselves and each other. We have built partnerships and learning journeys, we have applied for and have been turned down funding opportunities. We also learned a great deal about what it takes to make an online learning platform and community come alive, while fully seeing the ways where we couldn’t make this happen as much as we would have liked. I often joked that I went to school to become a social worker, not to learn how to re-launch a tech startup. However, beyond being a simple joke, the reality is that Wayside is similar to many social change movements and challenges. It was, and is, complex. 

Wayside is still somewhat amorphous ten months later and the future of Wayside is yet to be written. To fully launch and hold an online learning community, you need dedicated resources and Inspiring Communities might not be able to do it on our own. We tried as often as possible to challenge the idea that Wayside needs to live on forever as a platform and community, as the lessons we learned and the relationships we formed are living on within us. Wayside and all of its moving pieces have forever shifted Inspiring Communities and the partners who worked with us on Wayside. 

Online learning and community building is more important than ever and we continue to explore how best to contribute in this space. 

Images: Icons made by Eucalyp from www.flaticon.com

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