Dear Winnipeg

Dear Winnipeg,

We are now less than a month away from a truly historic event: the re-opening of Portage & Main, our downtown’s premiere intersection, to pedestrian crossings. But that’s only indirectly the topic for today. What this letter is actually about is how a butterfly flapping its wings in Winnipeg can cause a tornado in Texas. Or as you’ll see, a stop sign in Texas.

If you immediately recognize that concept as the butterfly effect, you’re either a fan of the 2004 movie of that title, or you already know about chaos theory. And if you already know about chaos theory, you’re either a fan of Jurassic Park, or you’re confusing it with a show on CBS.

It’s highly unlikely you’ve actually been studying a very specific branch of mathematics that examines how within the apparent randomness of chaotic complex systems, there are underlying patterns, interconnection, feedback loops, repetition, self-similarity, fractals and self-organization, with sensitive dependence on initial conditions.

Although, if so, good for you! Because that was a mouthful.

More simply, what chaos theory says is that, in complex systems, things that seem random and unrelated often aren’t. It’s just that the relationships are so interconnected, that even though there is a cause-and-effect, it’s impossible to make accurate predictions about them, because even a small change can lead to very large differences later on. That’s the butterfly effect.

So back to Portage and Main.

For all the non-Winnipeggers reading out there, as well as those of you who do live here but weren’t born in the 1900s, there was a time when people were allowed to cross the street at every intersection in our city. But in 1979, as part of a downtown renewal scheme, a 40-year deal was struck with some developers to force people to use newly-built underground tunnels at Portage & Main instead of just crossing the street like a normal person.

Then in 2018, one year before the expiry of that 40-year contract, a ballot measure was added to the regularly-scheduled municipal election to gauge the appetite of Winnipeggers for removing the concrete barriers that had stood for nearly four decades.

It didn’t need to go to a vote, but it did anyways. And this is where the real story begins.

I know, longest intro ever. Sorry.

You have to recognize that 2018 was a very different time. COVID and Dear Winnipeg didn’t exist yet. BlackBerry and the Arlington Bridge still did.

While it might seem like a no-brainer to those reading this today, at the time, it actually became an intensely divisive election issue. Worse yet, to many it seemed like the vote around Portage & Main was also happening in a void of reliable information, context, and nuanced discussion.

But what would happen next would cause BlackBerry to go out of business and COVID to spread around the world. Ok, probably not, but with chaos theory, we can’t completely rule it out. After all, maybe those aren’t random and unrelated, maybe the relationships are just too complex for us to grasp.

That said, one subsequent event that I can assure you is related is the beginning of Dear Winnipeg.

Because it was in response to these goings-on that a core group of about a dozen like-minded citizens decided to form a coalition to convince Winnipeggers to vote Yes to re-opening Portage & Main.

Full disclosure: I was not one of those citizens. But I can tell you who two of them were: Alyson Shane and Adam Dooley.

I know that, not because their names were constantly in the news over the months leading up to the 2018 vote (although they were), but because of a fateful encounter on an august summer evening that, uh, August.

My wife and I were out for an evening in the Exchange District, taking in the music and people in Old Market Square after having had a delicious dinner, when we walked by a modest table staffed by two people who were giving up their Friday night to help educate their fellow citizens on the benefits of a walkable downtown. They had pamphlets and maps, and they were friendly, energetic and passionate.

They were Alyson and Adam.

We stopped to chat with them, not because we needed convincing (we were already firmly in the Yes camp, for obvious reasons), but because we were curious. Why would they, and all the other people in the Vote Open group, take on the mammoth task of trying to educate an entire city?

As they told us, they just loved this city and wanted to see it do well, and they were willing to spend their own time doing what they could to make that happen, despite incredibly discouraging odds.

While this encounter likely didn’t even register for them, it stayed with me, even now almost seven years later.

Even though my wife and I bought the T-shirts, donated money, and volunteered to deliver flyers in our neighbourhood in support of the Vote Open campaign, that encounter was, more than anything else, the moment that got me thinking about how I could do more to contribute to my city. If people like Alyson and Adam were stepping up, what was stopping me? That’s why, only eleven days after the vote came in a resounding No, by a two-thirds margin, I was registering the domain name for Dear Winnipeg.

My goal was always to help make my own city more financially sustainable for future generations. And while I hoped to have an influence here, I never could have predicted that this conversation would resonate with folks outside of Winnipeg.

As I’ve mentioned before, nearly two thirds of those reading here are from elsewhere, mostly in Canada and the U.S., but also Australia, New Zealand, Europe and South America. And it’s been absolutely incredible to hear from you over the years, so I’d like to share a few stories from some who gave me permission to.

Ian McGregor in Concord, New Hampshire told me that these writings inspired him to become an appointed member of his town’s transportation advisory committee, get to know his city councillors and the staff working for his city, and join neighbourhood groups to advocate for smarter policies (backed up by math).

Ian has also since started writing op-eds for the local newspaper on topics such as questioning public subsidies for development, and advocating for safer streets.

And several months ago, I got an email from David Merz, Jr., a city council member in Castroville, Texas. To this day, reading it gives me goosebumps, so I’ll just let you read it (lightly edited for length):

I had written you a while ago to say that you and your blog had inspired me to speak up in my city and eventually run for city council. I thought I would give you an update.

Tonight, walking home from the council meeting, I felt like I really won for the first time. One of the items on the agenda tonight was a discussion on whether and when to install new stop signs requested by citizens. Our existing Traffic Calming Policy has about nine steps, and any of the first eight can result in the request being discarded with no change. If a request makes it through all nine, an engineer is hired to design a traffic calming solution that will go in the next time the street is rebuilt – and we have streets over 25 years old.

This topic has come up three times in the last three years. Each time has gone the same. One councilman said that we should do something. One councilman (a retired traffic engineer) said we have too many (and too chaotic) stop signs and we need to hire an engineer to redistribute them all. The other three murmured soft agreement with the retired engineer.

Tonight, I joined the first councilman and argued that citizens who live on streets should be listened to over engineers who live in a different city entirely. We suggested stop signs should be put up on temporary bases and, after a few months, the citizens who requested them should tell us whether they worked. If they don’t, we should try other traffic calming devices (speed bumps, chicanes, etc.). This time, we had two council members murmuring in support of trying to fix the problem. (I replaced the third murmurer.) This is the direction the council decided to go.

Before tonight, I have stood up for this group or that group. Before tonight, I have helped push towards or away from some action. Before tonight, I have been a vocal lone vote. However, today was the first time I felt like the Council did something GOOD that it would not have done without me. This is an issue that has come up three times before, but this time had a different outcome. We may not have officially replaced the do-nothing-at-all-costs Traffic Calming Policy, but we are making the city more responsive to its citizens. Stop signs are not the ultimate in traffic calming, but we have opened the door to finding what works best. We have kicked off a process that will make our streets safer for my wife, kids, and neighbors. Baby steps.

Today, I feel like my city is better because I stood up and said something.

And, partly, I stood up and said something because you inspired me. So thank you, Michel.

It blows me away that I’ve written words that inspired someone in Texas to run for office and take steps to make their community safer, or someone in New Hampshire to get appointed to their local transportation advisory committee and become a vocal advocate to better their city. But it shocks me even more that I might never have written those words at all if it weren’t for the humble actions of Alyson and Adam that evening in 2018. In retrospect, I can see the line of causation, but I never could have predicted it from the beginning.

Last month, I gave a talk in Brandon, Manitoba to over a hundred municipal administrators on the topic of sustainable municipal finance. Next week, I’ll be in Providence, Rhode Island to co-present with Chuck Marohn on a city finance tool I helped contribute to. And I even have a best-selling book that the administration for the City of Selkirk has bought for each of its council members. How crazy is all that?

And now all of those people are inspiring others in turn, causing a growing ripple effect.

Alyson passed away late last year, so she will never know the wide-ranging impact she was able to have. But I’m hoping that by writing this, you will know her impact: you’re only reading this because Alyson and Adam decided to give some of their time to making their city a better place. And I hope that can inspire you to start, or to keep going, in your place. What you do makes a difference, even if you don’t see it right away, or at all.

Cities across North America are in serious trouble, and it’s easy to get discouraged when faced with the enormity of the challenge of having to change basically everything about our approach to city-building. But that shouldn’t stop us from trying. Because no action is too small or too insignificant. Even if your action doesn’t lead to successfully achieving your objective today, it might still years later. Or, maybe your action inspired someone else to act, which inspired someone else, which inspired someone else, and now life is better in another city because of you, even if you’ll never know it. Your own personal version of the butterfly effect.

So when I cross Portage & Main as a pedestrian for the first time at the end of this month, I’m going to be thinking about Alyson and Adam, and how because of them, there’s a new stop sign halfway across the continent currently improving lives for people in Castroville, Texas. That’s the kind of stuff that keeps me hopeful.

Love,

Elmwood Guy

P.S. In a neat little full circle feedback loop, I was recently invited to speak as part of The Forks’ Lectures & Lagers series by none other than Adam Dooley, who is now the Director of Corporate Communications at The Forks, here in Winnipeg. So, if you missed last week’s book launch (or if you were there and didn’t get your fill of me yet), I hope to see you at The Forks on Friday, June 13th, 2025, from 6pm-7pm!

This event is in support of The Forks Foundation, and will feature a reading from my book, followed by a Q&A discussion with moderator Johanna Hurme of 5468796 Architecture.

Tickets are by donation to The Forks Foundation. Full details are here.