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Olivia Chow at a campaign event, surrounded by supporters

Recently, Toronto elected Olivia Chow, the city’s first racialized woman mayor, and since that time I’ve not only reflected on the significance of this milestone, but also the ways we can define and co-create a civic culture of support to address our most intractable challenges. My mind traverses back to the evening of the election and my walk through Toronto’s Yonge-Dundas Square, towards the Citytv studio, where I was scheduled to participate on a real-time election night panel. 

While navigating unhoused individuals debating with unrelenting demons, corner boys selling crack, which some say since COVID has made a ferocious comeback, and young girls selling sex slipping into the passenger seats of men driving respectable family sedans — the stakes of the election felt undeniable. 

Hovering beneath a stench of human feces, despair was on full display, in a public space that many imagined would showcase the very best of our beloved city — culture, connection and spontaneous delight. It was clear that instead of investing in infrastructure and social programs, former Mayor Tory acquiesced to powerful political elites — both the province and his voter base — intent on starving the city regardless of the undeniable cost. 

I settled into the greenroom, nervously nibbling on salad topped with tofu and avocado, joining former city councillors Denzil Minnan-Wong and Joe Mihevc. Within moments Mr. Minnan-Wong laments what he describes as the “Dundas Square situation,” pointing to broader concerns pertaining to the city’s “decline” and “neglect,” which he’d previously detailed in the Toronto Star in the fall of 2022. That was back before news of the former mayor’s affair with a young staffer broke, precipitating the by-election that brought the three of us — along with Brampton Mayor Patrick Brown — together for Toronto’s eagerly anticipated inflection point. 

The three of us agreed on the abysmal condition of Dundas square, and far too many public spaces across the city. However, Mr. Minnan-Wong was a long-time councillor who championed Mayor Tory, and directly supported the very policies and lack of investments contributing to the issue he now took umbrage with. This contradiction was consistent with a common strain of political amnesia and lack of accountability. An hour later, while discussing the by-election race on camera, he reiterated the same concern, this time pledging his — and John Tory’s — love for Toronto. Undistracted by greenroom salad and nerves, I replied, “Dundas Square is not what love looks like.” 

Despite a harrowingly close challenge from Ana Bailão, former City Councillor and Deputy Mayor, Olivia Chow — a  long-time progressive public servant and community champion — ultimately emerged victorious. In addition to a sense of immense relief for our city, I also felt gratitude for mayoral candidates Chloe Brown and Josh Matlow, two other strong progressive contenders, who ran intelligent and compassionate campaigns with integrity. I exchanged a smile with former Councillor Mihevc as the Citytv broadcast captured live congratulations and commitments of support from several defeated mayoral candidates. The panelists graciously expressed the same. 

I was elated for this milestone as well as the expressions of support across partisan lines. Equally important, I was optimistic about how Ms. Chow’s expertise and lived experiences may benefit everyone. At the same time, I was aware of the challenges ahead of her, both in terms of the range of complex city-building issues and the added burden of being the first racialized woman to lead the City of Toronto. 

An incoming Toronto mayor, regardless of identity, would be called to confront unprecedented challenges, including housing affordability crisis, neglected public spaces, and a lack of safety. However, as a “first,” Mayor-elect Chow will be expected to address these and other complex issues, while navigating an often-invisible dimension of challenges related to her identity. As a racialized woman leading a bi-national practice focused on public space design and policy, I often collaborate with professionals and elected officials occupying top levels of municipal leadership. While I feel privileged to be the Principal of a practice with the influence to contribute to positive institutional change, it is impossible not to notice that very few of my colleagues in leadership roles are women. And the ones that are? They’re typically held to unreasonably high standards while being over-extended and under-supported, which is amplified for racialized women and others leading at the intersection of additional marginalized identities.

While I wouldn’t presume to speak on behalf of Mayor-elect Chow or any woman leaders, I have a deep understanding of structural gender-based challenges within the context of public service and city-building. Although clearly distinct in terms of prominence and stake, Mayor-elect Chow’s victory evoked experiences that I — and many other women — have faced throughout our careers. From the outset of my career as an atypically young and  “first” Black woman cultural funder and policy maker within a provincial agency, I’ve experienced everything from being appointed to lead a diversity committee within the first week of work (without consultation) to being “accused” of being an affirmative action hire — despite the lack of  a Canadian affirmative action policy — to being expected to single-handedly repair historical harms between institutions and all historically marginalized communities. I’m not special. These and other challenges are not distinct to me; they are the price of entry for every “first.” There’s an understanding that a part of the job is to graciously rise above every unkind comment and unfair expectation. And most of all, as women leaders in roles unintended for us, to never ask for support. 

This unspoken professional ethos, embraced by women leaders of all identities, is what prompted me to compose a brief Twitter thread focused on how we, as engaged constituents, could deliver on our promise of support to Mayor-elect Olivia Chow for the benefit of our city.  

The support I’m calling for is not just about Mayor-elect Chow, it’s about creating a civic culture that creates fair institutional conditions for women to lead. By this I mean, understanding that new leaders, especially “firsts,” will bring new perspectives. This often contravenes established norms, resulting in discomfort. A healthy civic culture critically embraces this discomfort, honestly interrogating the validity of both long-standing and new approaches. It also creates room for new leaders to explore and fail — free from expectation for them to perform any aspect of their personal identities or to be a single voice for any one group. Fostering this type of civic culture requires everyone to practice curiosity, respect, and most of all, hands-on involvement. Realizing this audacious vision is impeded by our inability to address basic, gender-based representation within city-building. 

Although numerous studies find that institutions with greater representation of women and individuals from other equity-deserving groups outperform those with less representation, far too many women continue to be locked out of leadership positions. The Canadian Women’s Foundation reported that, “35.6 per cent of women hold management occupations and 30.9 per cent hold senior management positions, and that “only 6.2 per cent of women of colour hold board, executive, senior management and pipeline-to-senior-management positions collectively, with Black women, Indigenous women, women with disabilities and LGBTQ2S+ women each holding less than 1 per cent of women-held senior leadership and pipeline positions, respectively.” Specifically, in Canadian municipalities, change is incremental; of the 3,525 mayors governing cities across the country, only 19.4 per cent are women

A map of Canada overlaid with percentages of women mayors in each province, adding up to under 20% of the 3,524 mayors across the country.
Writing in Policy Options in 2019, researcher Katherine Sullivan identifies that under a fifth of all Canadian mayors were women. Image via Katherine Sullivan/Policy Options.

Fortunately, some organizations are beginning to address gender-based inequity in city-building. The Federation of Canadian Municipalities, which coincidentally stewards the Jack Layton Fellowship, an award honouring the Mayor-elect’s late husband, also bestows a Canadian Women in Municipal Government Scholarship. The award is geared towards secondary students contributing to student councils and other peer leadership bodies. Also, the Equal Futures Network, hosts a list of Canadian women mayors and First Nations band council chiefs. This list is accompanied by an informative map, and a prompt encouraging individuals to amplify the work of these women leaders. While such initiatives are laudable, they aren’t enough to address the intractable and often-invisible challenges of women’s day-to-day leadership experiences — including those of trans women and gender diverse individuals — or many of the broader structural issues.    

Although I wouldn’t presume to speak for Mayor-elect Chow or any other women leaders, I’ve experienced and witnessed these common yet predominately unspoken challenges. For decades, women leaders have been expected to strike the “perfect” balance — being confident but appropriately humble, attractive but never alluring, assertive but a bit of a delicate daisy. Beneath scrutinous stares, many of us have concealed fatigue from working into nights and weekends, suppressed tears, and performed under tremendous pressure. And while I am proud of our collective perseverance, women leaders are deserving of support, whether or not it is explicitly asked for.

For an entire gender, stereotyped as “weak” and “fragile,” asking for support is a perilous proposition. Many women leaders are raised to ignore or diminish obstacles as a way of overcoming them. Moreover, the concept of leadership within patriarchal institutions is rooted in notions of personal power and persona rather than collaborative vision and collective action. Although there is power and vulnerability in asking for help, understanding this complex dynamic removes the sole responsibility of accessing support from any one woman leader, and points to a broader cultural shift. What’s required now is understanding that voting to elect a leader, especially a leader occupying a role where they’ve been historically excluded or unrepresented, is an incomplete expression of support. It’s the beginning, not the end, of the city’s transformation.

Based on Mayor-elect Chow’s campaign performance and long-standing public service, I am confident that she will play an integral role in creating a civic culture that cuts through the sluggish systems and the apathy that has come to define City Hall. Her job is to lead institutional change guided by her expertise — and the expertise of City staff — along with her lived experiences. Our job is to hold her accountable and support her, because achieving true transformation requires all of us.

Lead photo by Ian Willms (Getty Images).

A New Mayor, a Broken City, and a Chance for Revival

As Olivia Chow prepares to take office, Jay Pitter reflects on how to create a civic culture that supports Toronto’s first racialized woman mayor and the entire city.

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