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Navigating Altitude: A Deep Dive into Progressive Leadership

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When I first came to Hollyhock in 2017, I knew that there was an opportunity to bring together digital campaigners and leaders working in advocacy, labour, and technology. My friend and former colleague (at NationBuilder), Jack Milroy and I had been talking about the idea for a number of years. I had also attended a number of the Web of Change gatherings at Hollyhock over the years and saw the power of convening progressive digital leaders. After consulting with many advisors and forming a robust national steering committee with Amara Possian, Armughan Syed, and Leah Bae, we launched the first Activate gathering at Hollyhock in 2018.  

The goal of Activate is to create a more connected, inspired, and better resourced progressive movement in Canada. Over the last five years, Activate has brought together over 500 progressive digital leaders at Hollyhock. Campaigns have been hatched, relationships have been built, people have found their people, and we have heard from some inspiring speakers. 

While Activate has been an incredible place to foster and inspire digital practitioners at every level, I have often heard from colleagues, friends, and participants that they would love a gathering like Activate specifically for senior leaders. With the escalating climate crisis and the rise of populism and authoritarianism the need for a gathering that brings together decision makers in advocacy, labour, and techonlogy seems more important than ever. This is why we launched Activate Altitude in 2023.

Activate Altitude is grounded on the premise that networked movements are better equipped to handle the complex challenges of our time than siloed organizations or sectors; that deep relationship between people is what provides the strength to our movements. The key outcome of Altitude is deeper, more trustful relationships. We understand that this is brave and challenging work. Systems are set up to encourage competition, scarcity, and inertia in the progressive movement. Fractures, mistrust, and dissonance amongst organizations can feel like the norm. 

Over the last number of months, I worked with my colleagues at Hollyhock to build the Activate Altitude cohort – 30 national senior leaders working in advocacy, labour, and technology. In all of those onboarding calls and in the 10  in-depth user interviews we conducted, I heard a deep desire for this work, to try to do things differently, and to build more trust, solidarity, and collaboration amongst Canadian progressives. I believe more in the need for this gathering now, than I did when we conceptualized it years ago.

Over 3 days in November, Altitude brought together 30 Directors and Executives across advocacy, labour, and the technology sector to build deeper, more trustful relationships, in service of a stronger progressive movement. Together participants explored avenues to building movement infrastructure, explored the challenges in the movement, and envisioned what is required – and how to collaborate – for the long-term health of the movement and the humans working within it. We were joined by special guest idea sparks including Melina Laboucan-Massimo (Indigenous Climate Action), Syed Hussan (Migrant Workers Alliance for Change), and Amanda Litman (Run for Something), who shared insightful provocations to shift the movement.

Activate Altitude is a beginning. It built on the strength of Activate and was facilitated by two world class facilitators in Sara El-Amine and Khari Wendell-McLelland. It was amazing to see these two facilitators work together for the first time! As a beginning, we understand there is room for growth. We are deeply grateful to our participants who have provided feedback to help us evolve the gathering. Some of that feedback includes: there were many voices missing from the table; we only just touched on the “next step” conversations that the movement needs to have (we are working to figure out how best to support those conversations happening); the location, though beautiful, was inaccessible for folks.  

On the last day of the gathering, I sat in that circle of 30 leaders and felt very grateful. Grateful that they had taken the time to share in the vision that relationships form the backbone of our movements; grateful that folks showed up with generosity and curiosity; grateful that folks made it out to Vaughn for Hollyhock’s first gathering in Ontario in 15 years; grateful that folks took two and half days away from their work and organizing (with all the suffering in the world right now) to join us in the view that a more connected movement will build the just, sustainable world we all know is possible.  

We can’t wait to continue to build on this work as we gather for Activate Hollyhock June 5-9 2024, and again for Activate Altitude in Winter 2025. 

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