Messy Cities: Why We Can't Plan Everything

Can messiness make our cities more liveable, lively, and inclusive?

Crowded streets, sidewalk vendors, jumbled architecture, constant clamour, graffitied walls, parks gone wild: are these signs of a poorly managed city or indicators of urban vitality?

Messy Cities: Why We Can’t Plan Everything argues that spontaneity and urban workarounds are not liabilities but essential elements in all thriving cities.

Forty-three essays by a range of writers from around the world illuminate the role of messy urbanism in enabling creativity, enterprise, and grassroots initiatives to flourish within dense modern cities.

With pieces on guerrilla beaches, desire lines, urban interruptions, and the inner lives of unlovely buildings written by experts from all walks of life, Messy Cities makes the case for embracing disorder while not shying away from confronting its challenges.

Zahra Ebrahim is an urbanist, educator, and strategist. Her award-winning work focuses on building bridges between institutions and their public, working with communities to co-design towards better social outcomes and leading some of Canada’s most ambitious participatory infrastructure and policy programs. She currently co-leads Monumental, a national organization focused on projects that advance fair, just, and culturally competent citybuilding, with previous experience leading organizations across multiple sectors. She is currently an Adjunct Professor at the Daniels School of Architecture and Urbanist-in-Residence at the University of Toronto’s School of Cities. She currently lives in Toronto with her partner, and their whippet, Zada.

John Lorinc is a journalist and editor. He reports on urban affairs, politics, business, technology, and local history for a range of media, including The Globe and Mail, Toronto Star, Corporate Knights and Spacing, where he is senior editor. John is the author of five books, including No Jews Live Here: A Memoir (Coach House Books, 2024), and has co-edited eight anthologies for Coach House, including The Ward (2015), Any Other Way (2017), and Messy Cities (2025). John is the recipient of the 2019/2020 Atkinson Fellowship in Public Policy and was the winner of the Writers' Trust Balsillie Prize for Public Policy, for Dream States: Smart Cities, Technology and the Pursuit of Urban Utopias (2022). He lives in Toronto.

Dylan Reid is a co-founder and now the executive editor of Spacing magazine, an award-winning print quarterly about Toronto urbanism and public space that recently celebrated its 20th anniversary. He is the author of the Toronto Public Etiquette Guide and co-editor of other books about Toronto. He was co-chair of the city government’s Toronto Pedestrian Committee and later co-founder of the advocacy group Walk Toronto. He is also a fellow at the Centre for Renaissance and Reformation Studies at the University of Toronto, and author of several scholarly articles about the history of cities in Renaissance France.

Leslie Woo is a dynamic tri-sector athlete known for her expertise in uniting public, private, and not-for-profit leaders to co-create innovative urban policy solutions. With over 30 years of experience as an urban planner, architect, and community activator, she has been central to shaping urban development in Canada’s largest metropolis. Leslie serves on the boards of Waterfront Toronto and the Yee Hong Centre for Geriatric Care and is a trustee of the Urban Land Institute. A Senior Fellow at the University of Toronto’s Munk School of Global Affairs and Public Policy, Leslie champions women city builders on her blog.