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Through the Cobwebs · Jul 6, 2026

Try a Little Empathy

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Brian Pincott · Through the Cobwebs

When I left Calgary City Council in October 2017 I did a few media interviews about why I was leaving and what the experience of being a city councillor was like. One of the questions I got was “what is the one quality you think is needed for a councillor?”. Without hesitation I said “empathy”.

Since moving to Winnipeg I’ve thought a lot about what real leadership at the municipal level looks like. Readers of this Substack will know that I am often shaking my head at lack of aspiration from City Hall. Being told too often that there is little that can be done, Winnipeggers have been worn down to accept the mediocrity of our public realm.

A City in Search of Leadership

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Jun 29

Here we are, 4 months out from the next municipal election in Winnipeg, and the most recent poll on Winnipeggers attitude towards city hall is, in a word, bleak.

It’s easy enough to write about the lack of leadership and point out the obvious. More challenging is to consider what the alternative is. And that got me thinking about my answer eight and a half years ago, that we need more empathy in our elected leaders. I would amend that today and add that we need more imagination as well.

We often hear from politicians that they’ve “received hundreds of emails” on an issue so therefore they must follow what the citizens want and vote a certain way. It’s an easy stance to take, it doesn't take much thought or consideration, just “do what you’re told”. For some, that is exactly what elected representatives should do.

Beyond the fact a city councillor can represent anywhere from 30,000 to 100,000 people and that “hundreds” hardly constitutes a significant portion, consider who is sharing their opinion. Those who contact their councillors, or mayor, are those who know how to access power. They know the mechanisms to make their voice heard. They have the ability, time, and resources to be able to write that email, make that phone call, attend that meeting (or several meetings) to ensure their voice is heard, and listened to.

But those few, and they are very few doing that regularly, are hardly representative. The elected representative should make sure that all voices are considered. In particular, they have a responsibility to those who are voiceless in the process.

While it’s easy to follow along with the few who share their voice, it is much more difficult to ensure that those who aren’t present are listened to as well. Elected representatives must be aware they are only hearing from a select segment of their constituents. It must always be remembered that while they are hearing from “hundreds” (and often much less than that), there are thousands who are shut out of the system.

Those who can’t ensure their voices are heard are working long hours, can’t afford internet, older and are not online at all, are overloaded in life getting kids to school and daycare and getting to work, those who can’t speak English, immigrants getting settled… when you think about all the barriers to participation, down to writing an email to your councillor, they can be overwhelming to a lot of people. As a result of all of those reasons when a councillor or mayor says they’ve “received hundreds of emails” to inform their decision, their voices are simply not present, they are not in the room.

This is why a key attribute for elected officials at the municipal level is empathy.

Likely someone who runs to get elected is already among the few who know how to access power and make their voice heard. They haven’t faced the challenges that so many others have in being able to participate in public life. It is up to them, once they are elected, to make sure that others are considered. We must make sure that we hold space for those who can’t get through the door.

It requires empathy to think about how decisions can affect others, particularly others who don’t share the same life. Empathy requires work, it requires reaching out to ensure that others are considered. Empathy is hard work. It can lead down paths that require more work to explain.

I have always been flummoxed by the extreme lack of imagination in elected representatives. I would sit in council meetings listening to great plans for the future, with everyone in agreement to the policy, but then not able to make the decision to move towards that desirable future because they can’t imagine anything different from today.

We don’t have to look far for an example. Every city has a plan to have more walking, cycling, and transit. Cities have adopted “plans” for the transportation “mode shift” as a primary means to reduce GHGs and address the climate crisis. This mode shift is embedded in climate targets for reaching net-zero GHG emissions by 2050. All laudable goals.

Yet, in Winnipeg, and many other cities, the move towards that net-zero target has been marginal at best. When residents (who know how to have their voices heard, who are most definitely in the room!) ask for more cycling infrastructure, more walkable areas, better transit, the answer from City Hall (and many others) is that we are a “car city”, so we can’t possibly invest too much in those other modes, because everyone drives and everyone needs to park. They lack the imagination to consider what the city might be. There is an inability to actually consider what the mode-shift they have espoused and asked staff to work on actually looks like.

Here in Winnipeg, the opening of Portage and Main is another great example. When asked in the last election whether they would open the Portage and Main intersection to pedestrians, all candidates save one said no. They would keep it closed, they simply couldn't imagine that allowing pedestrians to cross the street wouldn’t create traffic chaos. The admonitions of those wanting a more walkable and bikeable city fell on political deaf ears.

But here we are, one year after the intersection opened up to pedestrians, and the Mayor hailing it as a great achievement of his first term, even though he was adamantly opposed to opening it. And rest assured, City Council didn’t decide to open it because it was better for walking, or because it support a more walkable city, they decided to open it because it was cheaper than the rehabilitation work required. Even when the right decision is made, there is still a deep lack of imagination.

Speaking of “imagination” my idea of what to do with the concourse is to turn it into an aquarium. Imagine the sculptures on the back of an aquarium wall, with beautiful fish swimming around… Imagine it! No really…. imagine it!

Empathy and imagination is hard. It requires work. It often means having to step out of one’s comfort zone. In politics, the reward (getting elected and re-elected) goes more often to those who respond to the “hundreds of emails” and do what they are told. It seems that we have degraded our politics to the rewards going to the most complacent.

We are trapped in a cycle of mediocrity where fewer people are engaged, the loudest voices are getting louder, and the more marginalized amongst us are sliding further off the table. The challenge is acute in Winnipeg, but it exists in many communities and cities across Canada.

Real solutions to the challenges we face require empathy and imagination. We need leaders who are willing to do the work. Leaders who are willing to not only support a better vision but are willing to take the necessary steps to achieve it. They need to make sure that no one is left behind, and for that to happen we need empathy, deep empathy.

We don’t have to invent new solutions, the examples are myriad. The solutions are known to activists and social workers, to academics and other municipal leaders. Residents need to demand more thoughtfulness, more empathy, and more imagination from our leaders.

We all agree on a better vision for our community. Governments are good at putting that vision into plans, whether they are a local transportation plan or a national climate change plan. We have whole libraries of plans and visions for the future. Local area plans and affordable housing plans, water treatment plans and wetland restoration plans. Each with their own set of strategies and targets.

And yet, each year, we see that the targets are not being met, that the strategies haven’t been implemented, that the vision remains just that, a vision for the future.

We are only held back by a lack of empathy and imagination.

We need leaders who can inspire us with their imagination, who can challenge us with their empathy.

We need someone to shake us out of our complacency.

brian

ps. I feel that this might become a series of posts that are related to municipal leadership and how we can get a better city. There are so many examples, books, studies, and people who have so much wisdom to share.

If you know of any great thinkers, authors, leaders, studies, websites, songs, or anything else that could inspire and challenge, let me know. I am always looking to learn more and expand my horizons.

b

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