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Kayla Smith on August 26, 2013, with the bicycle she retrieved from a thief after it was stolen from her in Vancouver the previous week.Rafal Gerszak/The Globe and Mail

Canadian journalist Charles Montgomery was in Mexico City in 2004 to complete the final edit of his book, The Last Heathen, when he was gripped by questions of why some cities work and some do not.

The Last Heathen was the account of his journey retracing the steps of his great grandfather, the Bishop of Tasmania, who set sail for Micronesia in 1892 to save the islanders from black magic and cannibalism. But the cityscape that surrounded Mr. Montgomery as he polished his words in Mexico held "more magic and more mystery, more unknowns, in the megalopolis than I experienced in the South Pacific, and more poetry."

Then he encountered Enrique Peñalosa, the charismatic, evangelical, ex-mayor of Bogotá, Colombia, who claimed to have made Bogatans happier by reinventing the cityscape. That meeting was the start of the project that would occupy the next five years of Mr. Montgomery's life. The result is Happy City: Transforming Our Lives Through Urban Design.

Happy City is one of five books nominated this year for the $25,000 Shaughnessy Cohen Prize for Political Writing, which will be awarded April 2. The Globe and Mail will feature interviews with each nominated author during the week of March 17. Read an interview with Graeme Smith on Canada's unfinished work in Afghanistan or Donald Savoie on the declining public service.

What prompted you to think about city design?

Honestly, it was Peñalosa and his grandiose statement that he had transformed his city, that he had maximized happiness in his city in his three-year term. A light went on for me. On the one hand, I was very skeptical because he wasn't able to show me empirical evidence that boosted people's subjective well-being, which is the economist's term for happiness. But, on the other hand, I was so compelled by the idea that the city, in its shapes and in its systems, could make or break my own happiness. And then, in my own life and in the lives of the people I loved, I started to see those systems at work.

A couple of villains emerge in the book. Cars, for instance, don't get a good rap.

I disagree. The book is not anti-car. In cities around the world where change is taking place to favour people over certain monolithic systems like car-oriented planning, there's always an outcry suggesting that a war against cars has been launched. But, in every one of these cases, the people who are planning cities and creating policies around how we use our common space are simply adding more complexity, more freedom ... The book does not demand that people get out of their cars. What Happy City argues is that all of us should have more choice in how to move around our cities.

But, in your book, the car seems be the shell that is keeping people from interacting with other people.

My concern is that, in planning cities just for cars, we have stretched our lives across the miles. And it's that time spent in the commute alone that drains us of the opportunity for social interaction. It's not just important because it's fun and comforting to hang out with other people – and it is ... But, what so many policy makers forget is that face-to-face social interactions have now been shown to be the prime driver of innovation and even GDP in cities. Geographers and their supercomputers have shown that the factor that corrodes face-to-face interaction more than any other is urban sprawl.

Big box stores on the edge of town don't come off very well in your book.

If our cities are to succeed in the next century, we need to offer people who live in suburbs the same freedoms, the same opportunities, and the same generosities as people enjoy in the best central cities. In subsidizing low-density, big-box sprawl – and this is what we do through our policies on urban highways and land-zoning development – we are actually pouring money into the least efficient urban forms. The big boxes pull in less property and sales tax per acre, and they create less jobs per acre – often 10 times less – than your average multi-storey mixed-use building downtown. So what cities have been engaged in is an urban Ponzi scheme where you have to keep pouring more money into more development in order to pay for the last round of development.

Much of your message seems to be that seeing other people and being with other people, even if we don't know them, makes us happy. Is that right?

(There is) tension that exists within all of us between the need to connect with other people and the need to control our interactions with strangers. So, as much as I advocate for us to nudge a little bit closer together, and as much as there are tremendous benefits to be gained by creating dense, mixed-use walkable places, the sad truth is that the only residential environment where people express as little trust in their neighbours as they do on the ex-urban fringe is the residential tower. People who live in residential towers are most likely to complain of feeling crowded and lonely at the very same time. So we need to be very careful about investing in the extremes in our cities – either building more big box sprawl on the urban fringe (or) verticalizing neighbourhoods and seeing the residential tower as the only affordable option. We need to find models in-between.

If there is one simple idea that you wanted someone who read this book to come away with, what would it be?

The core message of the book, which I hope can be comforting for policy makers and individuals, is the notion that the happier city and the greener city, the low-carbon city, and the resilient and rich city are all the same place. And we can all build that place together. But it requires a sober second thought whenever we are making decisions around our complex systems.

Do you have to start from the ground up then?

No, we can absolutely retrofit our suburban town centres, just as we are retrofitting our central cities with fine-grained urban infill. This is the exciting notion. People who want to live in big houses with big yards that are only accessible by car will always have that option. All we're saying is that we need to invest in places that offer people more freedom so that even those people who insist on driving might have a village to drive to, and there might be a rapid transit stop there for them. And everyone's life will get easier, everyone's life will get more connected. They will get more time with their families. They will get healthier. They will eventually find they have more money in their pocketbook.

This interview has been edited and condensed

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