Dear Winnipeg

Dear Winnipeg,

Next week will mark the 7th anniversary of my very first letter here. At the time, I wasn’t planning on this being a long-term project. Naïvely, I expected I’d have said everything there is to say in, at most, a year. And yet, here we are, more than 2,500 days later, and there is still so much left to say.

Looking back, it’s pretty incredible what it has all led to. I started out as just a guy from Elmwood trying to better my community and my city with an educational, and I hope entertaining, blog on city issues. Since then, I’ve had a lot of my work republished in places such as Strong Towns and Streetsblog USA. I’ve been quoted in the media. I’ve done interviews and appeared on podcasts. I’ve had a newspaper column, a bi-weekly radio feature, and I’ve appeared regularly on TV as a political commentator. I’ve travelled to cities throughout North America to speak about municipal finance. I’ve contributed to the development of new municipal finance tools. I’ve consulted with cities and advocates alike to help them understand the financial trajectory of their place. I’ve written a book.

I truly believe that, for all the turmoil in the world these days, change starts at the local level, in your community. It’s why I’ve also been actively involved in my neighbourhood with various organizations such as the Glenelm Neighbourhood Association, Reimagine Elmwood, the East Kildonan-Transcona Residents Advisory Group, and quite a few more.

I haven’t done any of it alone. My amazing wife, Emma, has been working alongside me the whole time. She’s been the editor for Dear Winnipeg since the very beginning, helping me refine ideas and communicate more clearly, and generally preventing me from making a public fool of myself. She edited my book, and co-edited the next two books in the series with me. She had her own weekly column writing for Strong Towns. She was quoted in the media. She did interviews and appeared on podcasts. And she’s also been involved with various organizations in the community, some overlapping with me, some completely separate, like Safe Speeds Winnipeg, Trees Please Winnipeg and Chalmers Neighbourhood Renewal.

We were proud of the work we were doing, and we really liked our little life.

And then everything changed.

In April, our city councillor passed away suddenly, triggering a by-election. It didn’t take long before we were inundated with requests from community members for Emma to run for Council. The answer was a firm but polite, no thank you.

But they kept coming back. Again, and again.

We knew this would mean a big change. Emma would have to step down from her board involvements in the community. I might even have to step down from some of mine too. In Winnipeg, city councillors have various ways of supporting community initiatives in their ward, including with funding. Many of the groups we had been working with had been receiving funding from the previous councillor’s office. Our involvement with those groups would pose a conflict of interest if she wanted to continue supporting them as councillor.

But many community members stepped up to say they would fill in our shoes. And so it was that in late June, after many, many long family discussions, we agreed to let Emma’s name stand on the ballot.

The summer was a whirlwind as the campaign got off to a roaring start. In all, over 100 volunteers contributed their time to doorknocking, flyer delivery, and so much more. It was really cool to see. Activity continued to ramp up right up until the votes were tallied on October 25th. That night, Team Emma took in nearly twice as many votes as the next nearest candidate. Emma would be on City Council.

And then reality set in.

We expected that Emma would be stepping away from her various involvements in order to take on this new role, and we also expected that it would impact me to a certain extent as well. After all, the councillor’s office helps many community organizations with grants and other supports — having me on their boards creates a conflict that would prevent her from doing an effective job as councillor. So we knew there would be some things I’d have to step away from too, for the benefit of the community.

As clear-eyed as we thought we were about the trade-offs coming into this, I don’t think either of us was prepared for how much it would be in all. In addition to Emma stepping down from her community roles, I’ve also had to step away from virtually all of my volunteer commitments (and we’re still waiting for determinations on a few other things).

Not only that, but we had not considered the many other things that aren’t conflicts of interest per se, but that could contribute to a difficult political environment for Emma, like my continued participation in city advocacy, media appearances, my book, and of course, Dear Winnipeg.

It’s not hard to see how having your spouse continually commenting on all the wrong things the City is doing could create uneasy working relationships with your new colleagues. Plus, appearances matter, and it’s difficult enough being a woman in elected office without that extra layer of complications tacked on.

Suffice it to say, this has been a huge upheaval to both of our lives.

We’ve been having a lot of complicated feelings during this time of transition, despite believing we’re doing the right thing. A deep sense of grief over having to leave many of the groups and initiatives that meant a lot to us and that we were making positive change with. Anxiety about life in the public spotlight. Ultimately, a lot of uncertainty: can we have more of an impact with one of us working “in the system” than we would with two of us working at a grassroots level in the community? We don’t know yet. But this is how we’ve been asked to serve our community, so we’re going to give it a try.

So does all of this mean the end of Dear Winnipeg?

I don’t know yet. It can’t continue in the same way as before. But at a time when there have never been more of you reading, there is clearly a need for it to continue in some fashion. What will it look like? I don’t know that yet either. There’s a lot to figure out. And I’m happy to hear suggestions.

But what I do know is that a lot of you are already carrying the torch. Keep doing it. Write op-eds. Create videos. Speak at Council. Get involved in your neighbourhood. It’s the best way to have agency and a positive impact as our cities will continue to face many challenges.

In the meantime, I’m going to continue the work I’m doing with cities that aren’t Winnipeg. And we’ll eventually figure out what my local involvement, and a new Dear Winnipeg, can look like going forward.

Lots of love,

Elmwood Guy

P.S. With the holidays coming up, I think this is as good a time as any to remind you that I wrote a (fun!) book on municipal finance which would make an excellent stocking stuffer for the city-lover, journalist, public servant or city councillor in your life! It has been getting amazing reviews from tons of incredible people. Check it out!

P.P.S. The second book of the series, That’ll Never Work Here by Patty Wiens is also out. Not for nothing, but I think it would also make a great gift!

P.P.P.S. I spoke with John Simmerman on the Active Towns podcast about my book (and a bunch of other stuff!), and the episode is being released as a Live YouTube Premiere tomorrow, November 28th, 2025 at 1pm Central time. I’ll be online and participating in the live chat, so if you’re available and have any burning questions you want to ask, I hope to see you there!