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Creating Brave Spaces for Conversation

As a workshop facilitator with Evenings & Weekends, Greg Wong creates vibrant spaces for organizations to share their struggles, opportunities, and visions for the future.

Emerging from these sessions are common interests and shared values that allow staff, management, Board, and community participants to thrive in their work together.

We asked Greg a few questions about the values that he brings to his facilitation work, and his own dreams for a healthier, more equitable sector.


Hey Greg! Tell us a little about the skills or perspectives that you bring to your work with Evenings & Weekends.

With Toronto’s high cost of living, being a working artist means having to hold down multiple jobs. I’ve generally juggled at least four positions, if not more, to help pay the bills. That’s given me a lot of rich experience in many different fields.

I’ve been active in student organizing and as the shop steward of our union sub-local, I’ve held all sorts of retail roles, and I’ve done a lot of community workespecially in harm reduction, mental health, and sexual health. As an artist and gig worker, I’m all over the city, behind a camera, on the stage, or making magic behind the scenes. I’m basically everywhere! I feel like I’ve already lived many lives in my small amount of time on this planet, and that I get to benefit fromand sharewhat I learn from all the people I meet and work with along the way.

As much as I hustle to make ends meet, I dream of one day being able to slow down, work less, rest more, and become more socially engaged. I spend a lot of time thinking about how difficult it is to maintain a healthy work-life balance, or the trade-offs between financial and mental health. As I’ve grown older, I’ve become better about making choices to curate only the kinds of work that I feel strike a balance between my passions, social purpose, and appropriate compensation. But the further along I get, the more I feel that the ability to make those choices is further out of reach for a lot of people.

Evenings & Weekends puts these questions at the centre of our approach. What are the stories, motivations, and trade-offs that inform how people are able to show up to their work day-to-day? Addressing these realities feels important if we’re going to keep pushing for new and better ways of working and being togetherways that we were promised during the peak of the pandemic years.

As a workshop facilitator with Evenings & Weekends, what do you think goes into creating a space in which people feel comfortable discussing occasionally difficult or vulnerable topics?

As a facilitator, I always try to show up to a space as my whole self. That sounds vague, but I think energetically it helps when you are fully present in how you engage with people. You’re creating a space for people to be able to bring forward parts of themselves that they may have trouble accessing or sharing, and there needs to be a mutuality there in spirit. Folks may not always recognize that, or take up the space, but it’s my job to put it out there first. How a facilitator may choose to do that is up to them.

That being said, I also think that practicing good boundaries is the other really key part of good facilitation. In order for folks to feel held, they need to feel like there is structure and moderation to support the space. I’ve been in plenty of situations where things start to feel chaotic because of a lack of active moderation. It can be tricky sometimes to balance mutuality and assertiveness, but when you find the sweet spot, that’s when everyone starts talking and new ideas emerge.

What are your overall hopes for the organizations that we work with? In your mind, what would a thriving sector look and feel like?

I hope that the organizations that we work with come away with better frameworks, not only for reaching their objectives with us, but for conducting their day-to-day work long after our projects together are complete.

The work we do highlights the existing value and power within the people who work at and interact with these organizations. Can we get people talking to each other? Can we really listen to them? What ideas will come out of that? If we can help bring that practice forward as a critical part of the organization’s culture, then the impact will extend far beyond the boundaries of our work together.

A thriving non-profit sector is one that is open, adaptable, and accountable. The pace of change is so fast that if you let your views or methods fossilize, it’s an easy pathway to irrelevance at best, and “cancellation” (in as much as that is a real thing) at worst. Everyone knows what’s terrible about working somewhere that feels exclusive, stagnant, crusty, and today you can earn a reputation faster than the speed of a tweet. But we need to invite dialogue instead of shutting it out. And that dialogue needs to come with meaningful follow-through and change. If that work doesn’t get done, how can we expect the actual work in the community to get done?

What excites you about working with this team?

Everyone that I’ve met from the Evenings & Weekends team is socially engaged, innovative, a critical thinkerand also downright lovely. Because we’re new and we are still expanding, I haven’t been able to get to know everyone as well as I’d like yet. But to me, there’s this real first date energy buzzing around when folks are in the same room together that feels electric and inspiring. Where we’re at, at this specific point in time, feels full of potential and optimism.

That’s a big motivator for me to show up. I am constantly learning new things and gaining new perspectives from my colleagues as well as having lots of belly laughs. I have so much great work on my plate at any given time that it’s the energy that makes it or breaks it for me, and vibes on this team are unparalleled.

What do you find rejuvenating outside of work?

Outside of work, I like to do things that get my mind as far away from responsibility as possible! So that looks like either restfulness (naps, hanging out with my cat, sitting in the park) or embodied activity (riding my bicycle, going dancing, working out, cooking a meal).

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