In this special series of interviews, YongeStreet sits down for a chat to get to know some of the most prominent city builders whose work, vision and passion for the city help shape Toronto’s present and future.

As Chief Planner for the City of Toronto, Keesmaat is uniquely aware just how tenacious urbanism and city planning efforts have to be.

“A city is what we make it,” says Jennifer Keesmaat. From a single tree to a sidewalk café or a multi-block development, she says, “I don’t actually believe anything just happens; there’s always intent. You can always trace it back to a person who had an idea. The outcomes we see in the city are the result of significant, concerted, tenacious effort.”

As Chief Planner for the City of Toronto, Keesmaat is uniquely aware just how tenacious that effort has to be. “It’s nearly impossible to point your finger at one person when you see a great outcome,” she says. “There are so many different players that come together—and I find that to be very inspiring, because I see myself as immersed in a whole network of people who care passionately about creating a great city, and so many people can have a role.”

This tone of passion and commitment is typical of Keesmaat; her excitement about city planning is contagious and might just be what Toronto needs. Born in Hamilton, she holds a Master’s degree in Environmental Studies from York University and worked as an executive assistant to Councillor Joe Mihevc. Then Keesmaat founded a planning and design firm called the Office for Urbanism, where she has worked on master planning initiatives in numerous Canadian cities from Vancouver to Halifax.

When Keesmaat was appointed in 2012, her personal style was not especially in synch with that of then-Mayor Rob Ford. She is a former tree planter and a mother of two who looks and dresses more like a stylish television news anchor than a pencil-pushing, number-crunching bureaucrat. She posts on Twitter regularly and runs a blog about urban planning matters called  Own Your City, and subtitled “The Official Blog of the Chief Planner of the City of Toronto”.

She has a broad outlook, a quick intellect and a creative disposition, which allows her to see the possibilities and pitfalls for this city as it develops. “Our biggest pro/con is two sides to the same coin, which is that we’re growing very quickly, and as a result we’re seeing transformation before our very eyes. Our neighbourhoods, streets, waterfront are transforming. At the same time, the risk is that you don’t have the time to step back and evaluate and make sure that you’re going where you want to go,” she says.

“This is why growth needs to be managed. We need to make sure it grows where we want it to grow and link that growth to investment in our parks, schools, transit—all of the infrastructure that make a city liveable.”

Keesmat can name numerous areas where Toronto has made the right choices, “which is one of the reasons why we are growing so quickly and why we’re attracting Millennials,” she points out. “We have a legacy of street grid in the core of the city: a tight urban grid which is very walkable. It’s one of the things that’s so lovely about Portland—which means that your buildings aren’t monstrous [and] pedestrianism, cycling and transit become viable.”

She also points to our ravine system, overlooked or entirely undiscovered by many residents. “Seventeen percent of our city’s land area is actually ravine,” she says. “We have done well in creating environmental regulations that have protected our ravines as key natural areas. We tend to take this for granted, but we in fact have a legacy through Queen’s Park, High Park and now the Waterfront of green spaces, which are a critical counterpoint to density.”

By preserving green spaces and concentrating density in the downtown core and along certain key avenues, “we have been able to protect our neighbourhoods,” Keesmaat says. “Many people in Toronto have main streets adjacent to their neighbourhoods; this is a unique character. You can walk to the corner store, the greengrocer, transit. In the absence of the grid, that becomes very tricky, and in the absence of green space, it becomes very challenging to add density.”

On social media, Keesmaat explores the idea of “theatricality”, which she describes as the quality of allowing people to see and interact with one another and with nature. “There’s a variety of ways that public spaces can bring people together: great dog parks, children’s play areas, main-street retail, great civic spaces,” she says.

“At the other end of the spectrum are places like Nathan Phillips Square, which can become places of mourning—as we saw after the deaths of Jack Layton and Mayor Ford—or celebration. Last fall when the Blue Jays were in the finals, even though it was cold outside, I was amazed to see people who gathered in the Square and stood outside to watch the games, even though I guarantee every one of those people had a television at home.”

It would be fair to say Keesmaat has lofty goals. “At the very highest level, my objective is to make the city more liveable, more sustainable, and a place where everyone can thrive,” she says. “When cities are done right, they’re inclusive places where people from all walks of life can thrive to the best of their potential.”

However, she adds, “cities, from their design, can also detract from that.” Poorly planned transit, a low walkability score, neighbourhoods with inadequate access to fresh food: all of these are among the factors that can hold people back, reduce their potential income and even have an adverse effect on their health.

“The way we plan the city is a key determinant,” Keesmaat says. “I use [the goal] of creating a city for all, that is both sustainable and prosperous for all, as a lens in all of our city planning decisions.”