Iain Montgomery

Escaping The Auto-Financial-Industrial Complex How a system built for growth turned everyday life into a debt-fuelled endurance test ... and why cities are now feeling the strain.

"We built an extraordinarily efficient system for a particular moment in history, and then kept optimising it long after its side effects outweighed its benefits."

This is a really good piece on the origins and outcomes of the suburban experiment. challengercities.substack.com/p/escaping-t...

Challenger Cities EP55: Impossible City - Paris in the 21st Century with Simon Kuper Listen now | Beyond postcard Paris lies a city of charlatans, supercharged suburbs, and astonishing state capacity. Simon Kuper's new(ish) book is the ideal guide to the current superstar poster child...

For anyone interested in how cities are changing: I spoke to the Challenger Cities podcast about my memoir of modern Paris, Impossible City. About the good, the bad, and the almighty anarchy that is Parisian cycling challengercities.substack.com/p/challenger...

Challenger Cities EP52: Culture as a Form of Wealth with Paul Owens Hewison defined culture as a public good. Paul Owens explains how the cities that believe that become far more vibrant, creative, prosperous and self-assured.

Haven't been here in a while, stuck in the darkside of X.

But this was such a good Challenger Cities conversation about the importance of culture, that it's worth a return.

open.substack.com/pub/challeng...

I knew Metrolinx were fucking useless, but this is a remarkable new low.

"Boxes where people get on and off trains" - Metrolinx, Head of Stations, said this directly to me when I asked how they would describe them to a child.

I will remember bsky exists. I will remember this place exists.

Challenger Cities EP28: Why North American Transit is Mediocre ... and How to Make it Actually Good with Reece Martin Listen now | What thousands of hours creating a transit YouTube channel can teach us about how to build better cities.

New Challenger Cities on how North America’s transit isn’t broken because we don’t know what to do.

Rather it's because everyone keeps pretending it needs to he reinvented from scratch.

@rmtransit.bsky.social on buses, bullshit and building better:

🎧 challengercities.substack.com/p/challenger...

Open BlueSky for the first time in a while, and wow, like an actual positive mention of Carney.

That's refreshing compared to the other place!

Urbanists Have a Communication Problem, and it’s Costing us Great Cities Can we stop lecturing people about what makes good urbanism, and start selling the feeling of better places to play, live and work?

This piece ended up doing really well, with both classical and 'accidental' urbanists.

Now can we start talking about them in ways people actually understand, and do more together, rather than gatekeeping it all.

challengercities.substack.com/p/urbanists-...

Making Innovation Work: An Explainer on the '5C' Innovation Canvas Clear the clutter and move forward with confidence. The ghosts of past innovation attempts still haunt most organisations. This canvas helps re-focus on what actually works.

For the full thing, you'll find it here.
nowornevermoments.substack.com/p/making-inn...

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If you’re leading innovation, don’t get buried in frameworks.
Use the 5C’s of Innovation Canvas to focus on what actually works.

Let’s clear the clutter and move forward with confidence. 💡🚀

#Innovation #Leadership #Strategy

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Want to try it?
Our Innovation Canvas is best used in a 2-3 hour session.
⚡️ Get your team together
🧩 Map where you are
🚀 Define the next steps for real progress

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Many organizations get stuck in corporate theater.
They run endless innovation sprints but lack real change.
The 5C’s Canvas forces teams to prioritize, cut waste, and move forward with clarity.

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Step 5: Move to Action
Innovation isn’t about more ideas—it’s about momentum.
🔹 Start Doing – What new initiatives are needed?
🔹 Keep Doing – What’s already working?
🔹 Stop Doing – What’s just creating noise?

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Step 4: Capture Insights & Implications
As ideas emerge, track:
📝 New opportunities
🤔 What assumptions we’re challenging
💡 Small shifts that can create outsized impact

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Great teams ask:
👀 Are we really listening to customers?
🛠 Are we testing and iterating fast enough?
💬 Do we reward bold thinking or shut it down?

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Step 3: The Five C’s of Innovation
We measure innovation against five key competencies:
🔍 Curiosity – Explore beyond your bubble
🎨 Creativity – Challenge the status quo
💪 Creed – Deep belief in your work
🔥 Courage – Push through failure
🏛 Culture – Make innovation part of your org DNA

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Airbnb reimagined accommodation.
Edison invented the light bulb.
IKEA used ingenuity to revolutionize furniture.
Knowing where your innovation fits helps teams focus on execution.

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Step 2: The Three I’s of Innovation
There’s no single way to define innovation. Instead, we explore:
💡 Imagination – Seeing new possibilities
🔬 Invention – Creating something truly new
🛠 Ingenuity – Hacking the system for smarter solutions

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Step 1: Set the Context
Before jumping into solutions, ask:
🔹 How did we get here?
🔹 What challenges do we face?
🔹 What outcomes do we really want?
Without this, innovation risks being just another buzzword.

Most organizations don’t lack innovation efforts—they lack clarity.
Too often, teams keep adding initiatives without removing what’s not working.
The 5C’s of Innovation Canvas helps answer:
✅ What to start
✅ What to keep
✅ What to stop

🚀 Clear the clutter and move forward with confidence.
Innovation is littered with abandoned labs, legacy frameworks, and stalled projects. Our 5C’s of Innovation Canvas helps teams refocus and take meaningful action. 🧵👇

Challenger Cities EP20: Rethinking Cities Through Lessons from Music, Psychology and Engineering with Nick Tyler Listen now (75 mins) | Urban design often focuses on hardcore infrastructure, but what about the people who use it? We explore how psychology, neuroscience and philosophy can make urban spaces work be...

Are cities stressing us out without us really knowing?

Bus stops triggering fear. 🚏
Cyclists who don't see you. 🚴‍♂️
Station lighting that doesn't illuminate. 🚆

Nick Tyler of UCL PEARL shares how cities mess with our brains and how to fix them. 👇

challengercities.substack.com/p/challenger...

A recent conversation with Mary Rowe of the Canadian Urban Institute for Challenger Cities was pretty refreshing. If you're having one of those days where everything feels overwhelming, focusing on the local can be a good solace.

challengercities.substack.com/p/challenger...

Cycling can transform cities into happier, healthier places.

In his recent appearance on the Challenger Cities Podcast, Chris Bruntlett chats with @iainmonty.bsky.social on how Dutch cycling culture can inspire cities worldwide.

CHECK IT OUT: ow.ly/nRhm50UFnsU

Toronto can actually do interesting Challenger City things. Worth checking out what is happening on the old Downsview Airport lands with 10 new neighbourhoods emerging over the coming years.

challengercities.substack.com/p/challenger...

Challenger Cities EP17: Cycling, Leadership and the Future of Urban Living with Chris Bruntlett Bicycles are more than a mode of transport—they’re a tool for creating liveable, inclusive cities. Why cities need to learn from the Dutch, and get brave with their leadership.

Cycling isn’t just a commute, it’s city transformation. 🚲 @modacitylife.com shares lessons from the Netherlands on bold leadership, cohesive networks, and why bikes + transit are the future. No copying Amsterdam—just building better cities.

challengercities.substack.com/p/challenger...

Challenger Cities EP16: Red Tape to Results; Rethinking Governance for Better Cities with Hayden Clarkin Hayden Clarkin argues that North America’s cities are stuck in a cycle of over-planning & under-delivering. We must prioritise outcomes, streamline governance and rebuild trust in public institutions.

How did North America go from world-class transit to $30M staircases & sunshades that don’t provide shade?

@thetransitguy.com doesn’t hold back, breaking down broken systems, bold ideas & how we can rebuild trust in our cities.

challengercities.substack.com/p/challenger...

Challenger Cities EP15: Trains, Pains and Automobiles with Thomas Ableman What some cities get so right about transportation, why some cities get it wrong, and how we can go about making the whole thing much better.

Why Swiss trains are like playgrounds.

Why Oslo sees autonomous vehicles as more than robotaxis.

Why Walthamstow should be on the transport tourism circuit.

& why bold leaders who back public transit always win.

My chat with @freewheeling.info for Challenger Cities.

shorturl.at/zMsDa

Will 2025 be the the year we stopped procrastinating and finally started building the future again? We never made the utopian future the tech and urbanist types promised us. We likely still won't ever see it, but we can at least get building bits of it again.

2025 was supposed to be sci-fi come to life, but all we got was better WiFi. The future didn’t fail from bad ideas; it failed because no one built them. Utopia isn’t perfection—it’s messy progress.

challengercities.substack.com/p/will-2025-...