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Iain Montgomery

@iainmonty.bsky.social
65 followers 39 following 71 posts

Innovation, Urbanism, Public Transportation & Design type stuff. Maybe a bit of Burnley FC, Edmonton Oilers, Minnesota Vikings too.

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Iain Montgomery @iainmonty.bsky.social · 15/09/2026
Why is it that as virtually every sector over the past 50 years has seen incredible improvement in productivity, the cost of constructing things like buildings or infrastructure is so much higher? A new paper called 'Chain Drain' might offer an answer. challengercities.substack.com/p/challenger...
challengercities.substack.com
Challenger Cities EP101: Chain Drain with Greg Lindsay & Bryan Boyer
Listen now (63 mins) | Why every project in the built environment is effectively a prototype, how we fail to learn from what we build and 4 futures that could follow. Once you see Chain Drain, you not...
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Iain Montgomery @iainmonty.bsky.social · 11/09/2026
For episode 100 of Challenger Cities, it felt appropriate to do a conversation about How Big Things Get Done ... which meant we had to go and get Bent Flyvbjerg on. Here's a bit of a highlight. challengercities.substack.com/p/challenger...
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Iain Montgomery @iainmonty.bsky.social · 11/08/2026
"The convenience of the privacy is very tempting. It's kind of fast food for the brain. You can avoid people." New episode with Ann-Britt Elvin Andersen and Jakob Norman-Hansen of BLOXHUB, on the paradox of proximity. challengercities.substack.com/p/challenger...
challengercities.substack.com
Challenger Cities EP96: The Paradox of Proximity with Ann-Britt Elvin Andersen and Jakob Norman-Hansen
Listen now | We were sold convenience, only to have bought disconnection instead. So what happens when you stop treating loneliness as a health problem and start treating it as a design one?
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Iain Montgomery @iainmonty.bsky.social · 05/08/2026
Mosaic runs a segment where staff stand up and talk about what they love after they clock off. Nearly every answer turned out to be about place: bars as infrastructure, networking as a luck machine, a coffee shop that's really a clubhouse. challengercities.substack.com/p/challenger...
challengercities.substack.com
Challenger Cities EP95: The 5-to-9 Episode with Mo, Laura & Nick from Mosaic
An agency's after-hours reveal more about how cities work than most masterplans. A bumper episode on nightlife as infrastructure, networks as luck machines and the clubhouse everyone dreams of.
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Iain Montgomery @iainmonty.bsky.social · 30/07/2026
"We are allowed to make things up." While the UK talks new PM and Manchesterism, the more interesting conversation with the same energy might be the Sussex motto: "we wunt be druv". New Challenger Cities with @willsh.bsky.social challengercities.substack.com/p/challenger...
challengercities.substack.com
Challenger Cities EP94: We Wunt Be Druv with John V Willshire
Listen now | Sussex has an old motto that means "we won't be pushed around like sheep" ... and it makes for a rather good conversation about how to create distinctive, worthwhile change in real places...
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Iain Montgomery @iainmonty.bsky.social · 24/07/2026
America is the most efficiency-obsessed civilisation in human history. It is also, by some distance, the most wasteful. It's actually an accounting problem. New Challenger Cities on a Montreal→Cincinnati road trip via Buc-ee's, Waffle House and taxidermied train stations. shorturl.at/21fQr
shorturl.at
The Most Efficient Way to Waste a Continent
What a drive from Montreal to Cincinnati ... via Rochester, Buffalo, Buc-ee's, the Waffle House and taxidermied train stations ... reveals about America's accounting problem.
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Iain Montgomery @iainmonty.bsky.social · 24/07/2026
You can't build a warm, human city with people who've been trained out of being warm and human themselves. This is a conversation on a workshop trying to put that back into the professional realm, applied to urbanism and place. challengercities.substack.com/p/challenger...
challengercities.substack.com
Challenger Cities EP93: The Maker is the Medium with Florence Okin and Sam Cohen
You can't build a warm, human city with people who've been trained out of being warm and human themselves. A conversation on a workshop trying to put that back into the professional realm.
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Iain Montgomery @iainmonty.bsky.social · 07/07/2026
This is such a good reframing of Italian urbanism from Giacomo Biraghi. Forget the romantic image of piazzas, and think more about how Italy does the industrial sprawl better than the North Americans. challengercities.substack.com/p/challenger...
challengercities.substack.com
Challenger Cities EP92: Cities Are Mental Weapons with Giacomo Biraghi
Listen now | Everyone in urbanism is arguing about the form of the city like the piazzas, the towers or the transit lines. But what if that the form was never really the point?
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Iain Montgomery @iainmonty.bsky.social · 03/07/2026
Rather lovely Challenger Cities episode to round out the week with @ballantine70.bsky.social. It's a bit random, which is good because it's partly about Random the Book, and how it applies to places we think we can perfectly plan yet obviously can't. challengercities.substack.com/p/challenger...
challengercities.substack.com
Challenger Cities EP91: Expanding Your Luck Surface Area with Matt Ballantine
Listen now | You can't manufacture serendipity, but you can widen your exposure to it and get better at catching it when it lands. Applying a shuffleable book about Random to the platform of place.
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Shiv Malik @shivmalik.bsky.social · 02/07/2026
I very much loved chatting with Iain about Forest City. He’s a great interviewer and we really got into the detail in how we could build the UK’s next city.
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Butterflies Katz ⓥ @butterflieskatz.bsky.social · 29/06/2026
A #mural by Dutch #artist Judith de Leeuw shows the Statue of Liberty covering her eyes (in shame) in Roubaix, France (in 2025, just before July 4th). Judith de Leeuw, also known as JDL #StreetArt, creates #murals worldwide (41 countries) to draw attention to social issues. info@jdlstreetart.com
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Iain Montgomery @iainmonty.bsky.social · 29/06/2026
New Challenger Cities episode today on Forest City 1 with @shivmalik.bsky.social ... a big, bold and ambitious idea that seems almost ideally suited for a moment where Britain is apparently going to be open to such things. challengercities.substack.com/p/challenger...
challengercities.substack.com
Challenger Cities EP90: It Only Sounds Mad Because We Think Small with Shiv Malik
Listen now | A journalist, a few thousand pounds and forty people working for free want to build a city for a million people next to Cambridge. The maddest thing about it is how sane it is.
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Iain Montgomery @iainmonty.bsky.social · 25/06/2026
I think Gil Penalosa might have developed one of the urbanism terms of the year. CAVE people ... Citizens Against Virtually Everything. The type of person the media thrive on, sapping the curiosity, creativity and courage of people as they go. challengercities.substack.com/p/challenger...
challengercities.substack.com
Challenger Cities EP89: To Do, Not Just Be with Gil Penalosa
Listen now | Lots of people want to be mayor. Very few want to actually do the job though. But what if almost everything worth doing turns out to start cheap, reversible and already within the mayor's...
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Iain Montgomery @iainmonty.bsky.social · 21/06/2026
Big fan of this week's Challenger Cities podcast guest ... because it's @urbancourtyard.bsky.social ... someone doing amazing things around reframing how apartment living could and should work in North America. challengercities.substack.com/p/challenger...
challengercities.substack.com
Challenger Cities EP88: The Neighbourhood is the Amenity with Alicia Pederson
Listen now | North America forgot how to build an apartment worth desiring. Alicia Pederson's fix is a thousand years old, hidden in plain sight behind the buildings and almost entirely illegal in man...
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Iain Montgomery @iainmonty.bsky.social · 16/06/2026
A bit of a recap from the recent Challenger Cities Salon we hosted in Montreal. And what happens when you throw the provocations around language and culture to a city that sees its identity through those lenses. challengercities.substack.com/p/dont-corre...
challengercities.substack.com
Don't Correct the Accident: A Tale from the Montreal Salon
What we learned from a night with Jacquelyn West, Phil Tabah, Greg Lindsay and Andy Nulman in conversation with ~70 hot Montréalers.
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Iain Montgomery @iainmonty.bsky.social · 15/06/2026
For the folks who are less into the Substack thing. Reminder that you can follow Challenger Cities on your podcast platform of choice incl. Spotify And I promise we've got some non-transport related episodes coming up very soon. open.spotify.com/show/7KeHikL...
open.spotify.com
Challenger Cities
Podcast · Iain Montgomery · Iain Montgomery of Now or Never Ventures interviews urbanists, creatives, transit and development types to explore how cities can punch above their weight and create distin...
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Iain Montgomery @iainmonty.bsky.social · 15/06/2026
It's wild how Canada is spending $250,000,000,000 on public transport at the moment, without any clear standards or training in the profession. It also explains why projects are delivered at great expense, with significant delays and meh outcomes. challengercities.substack.com/p/challenger...
challengercities.substack.com
Challenger Cities EP87: Bringing Sexy Back to Transit with Mark Salsberg and Jonathan English
Listen now | A quarter trillion dollar industry Canada doesn't teach, nor promote and is almost embarrassed about those with a passion for. This is a conversation with two gentlemen intent on fixing t...
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Iain Montgomery @iainmonty.bsky.social · 08/06/2026
New Challenger Cities episode is all about High Speed Rail, and specifically, how it could and should work in Canada. In many ways, it's covering what the project by Alto and the cabal of naysayers are neglecting. challengercities.substack.com/p/challenger...
challengercities.substack.com
Challenger Cities EP85: Canada Needs a Railway Architect with Michael Schabas
Listen now | Fifty years of building railways taught Michael Schabas one rule above all, and it's the one Canada keeps ignoring on the way to spending $100 billion.
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Iain Montgomery @iainmonty.bsky.social · 03/06/2026
Good new Challenger Cities episode today. And it's one of what will be quite a few very transport heavy ones coming up. We're talking about why is it so hard to do innovation in public transport, and how Richard Fisher might solve for that. challengercities.substack.com/p/challenger...
challengercities.substack.com
Challenger Cities EP84: The De-Risking Industrial Complex with Richard Fisher
Listen now (73 mins) | Innovation in public transport is hard. Because not only are transport operators almost allergic to what is novel and therefore risky, but the venture funding ecosystems have th...
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Iain Montgomery @iainmonty.bsky.social · 02/06/2026
What if we stopped settling for cities that'll do, and pushed on for ones that are wonderful? Last week I had a couple of captivating afternoons at Utopian Hours in Rotterdam, and it was full of creative inspiration and ammunition. challengercities.substack.com/p/what-if-we...
challengercities.substack.com
What If We Made It Wonderful?
Utopian Hours in Rotterdam was a rare event about cities that would captivate anyone who's ever loved a place without needing a planning degree.
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Iain Montgomery @iainmonty.bsky.social · 01/06/2026
I will get better a sharing Challenger Cities episodes on here. I will get better a sharing Challenger Cities episodes on here. I will get better a sharing Challenger Cities ... But this one is a good one, because @freewheeling.info is on here. challengercities.substack.com/p/challenger...
challengercities.substack.com
Challenger Cities EP83: A Little Piece of Switzerland in the Derbyshire Hills
Listen now | On building a small piece of Switzerland in the Derbyshire hills, why trams really do matter, and what happens when you start designing transport around people instead of vehicles.
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Iain Montgomery @iainmonty.bsky.social · 15/05/2026
Three groups spent decades fighting the Pickering airport and they won! Now they have to agree on what comes next, which is trickier. Ken Greenberg has spent his career building rooms where that disagreement gets resolved. New Challenger Cities: challengercities.substack.com/p/challenger...
challengercities.substack.com
Challenger Cities EP81: A Chair in the City and a Stool at the Rouge with Ken Greenberg
Listen now | Having spent the best part of 50 years putting the right people in the same room. The Pickering Lands are the latest test to bring people with different needs and desires around a common ...
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Iain Montgomery @iainmonty.bsky.social · 11/05/2026
We celebrate entrepreneurship as a creative act. The willingness to work at the edge of what's permitted, expand mindsets, spot value nobody else has bothered to look for. In cities and infrastructure, we've forgotten this is even allowed.
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Iain Montgomery @iainmonty.bsky.social · 11/05/2026
Maybe Kier can commission a study, into a review, about maybe doing a consultation, that will result in a consulting engagement about trams.
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Iain Montgomery @iainmonty.bsky.social · 05/05/2026
New Challenger Cities episode out today with Gerald Babel-Sutter of Urban Future. One I particularly enjoyed for the mutual shared distrust of the obsession with "best practice". challengercities.substack.com/p/challenger...
challengercities.substack.com
Challenger Cities EP79: The Best Practice Industrial Complex with Gerald Babel-Sutter
Listen now | Most urbanism conferences celebrate what cities got right. Urban Future was built specifically for everything they got wrong, and that turns out to be where the real insights are to be fo...
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Iain Montgomery @iainmonty.bsky.social · 04/05/2026
One for the Toronto people into cities and innovation stuff. The first Challenger Cities salon is taking place next Wednesday the 13th May. #toronto #urbanism #innovation luma.com/j8dtoga0
luma.com
Challenger Cities Salon - Toronto · Luma
Toronto keeps telling itself it's world class. It should be asking why it keeps underperforming what it already has. A genuinely diverse, economically…
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Iain Montgomery @iainmonty.bsky.social · 01/05/2026
No is the safe answer. It's also why Canada can't build anything. Canada isn't short of money, ideas or expertise. It's short of people allowed to say yes. Jen Angel of Evergreen on the permission problem as it relates to infrastructure. challengercities.substack.com/p/challenger...
challengercities.substack.com
Challenger Cities EP78: Saying Yes More with Jen Angel
Listen now | Canada has the money, the expertise and, for the first time in a generation, the public appetite. What's missing is enough realisation that we do have the permission to say yes.
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Brent Toderian @brenttoderian.bsky.social · 28/04/2026
“In Toderian’s view, the dividing line between cities that succeed and those that stagnate isn’t geography, wealth or even size—it’s mindset. Some places embrace experimentation, risk…Others default to caution, delay, and a reflexive belief that change is impossible.” momentummag.com/urban-truth-...
“We could never do THAT in OUR city.”


Leadership doesn’t make excuses.

Via the Urban Truth Collective

Background photo of people walking along a pedestrian street and people-place successful and vibrant in Central Montreal. A street transformation that took community leadership, energy and action, and a spirit of experimentation, rather than excuses or risk-aversion.
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Iain Montgomery @iainmonty.bsky.social · 28/04/2026
A good reason to remember bluesky exists is to find where @alexbozikovic.bsky.social went from that other place. Because I have a new Challenger Cities out feat. him today, and I must say it's rather a good one of diagnosing a wee bit of Toronto. challengercities.substack.com/p/challenger...
challengercities.substack.com
Challenger Cities EP77: The Will To Build with Alex Bozikovic
Listen now | Toronto has the talent, the money and the bones of a great city. What it keeps failing to find is the will to build one.
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Iain Montgomery @iainmonty.bsky.social · 28/04/2026
I need to do a better job of remembering this place exists.
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Daniel Herriges @dpherriges.bsky.social · 07/01/2026
"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...
challengercities.substack.com
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.
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Simon Kuper @simonkuper.bsky.social · 12/12/2025
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...
challengercities.substack.com
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...
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Iain Montgomery @iainmonty.bsky.social · 24/11/2025
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...
open.substack.com
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.
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Iain Montgomery @iainmonty.bsky.social · 02/06/2025
I knew Metrolinx were fucking useless, but this is a remarkable new low.
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Iain Montgomery @iainmonty.bsky.social · 28/05/2025
I will remember bsky exists. I will remember this place exists.
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Iain Montgomery @iainmonty.bsky.social · 28/05/2025
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...
challengercities.substack.com
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.
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Iain Montgomery @iainmonty.bsky.social · 18/03/2025
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-...
challengercities.substack.com
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?
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Iain Montgomery @iainmonty.bsky.social · 07/02/2025
🚀 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. 🧵👇
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Iain Montgomery @iainmonty.bsky.social · 30/01/2025
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...
challengercities.substack.com
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...
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Iain Montgomery @iainmonty.bsky.social · 21/01/2025
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...
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Dutch Cycling Embassy @dutchcycling.nl · 13/01/2025
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
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Iain Montgomery @iainmonty.bsky.social · 10/01/2025
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...
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Iain Montgomery @iainmonty.bsky.social · 20/12/2024
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...
challengercities.substack.com
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.
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Iain Montgomery @iainmonty.bsky.social · 18/12/2024
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...
challengercities.substack.com
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.
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Iain Montgomery @iainmonty.bsky.social · 13/12/2024
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
shorturl.at
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.
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Iain Montgomery @iainmonty.bsky.social · 03/12/2024
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-...
challengercities.substack.com
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.
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Iain Montgomery @iainmonty.bsky.social · 02/12/2024
The longer we plan, to more we stay in the riskiest place by maintaining the status quo. Which is weird because the whole point of starting the plan is because the status quo probably isn't working very well, or won't for much longer. innovatorssocialclub.substack.com/p/the-tyrann...
innovatorssocialclub.substack.com
The Tyranny of the Perfect Plan
Planning is seductive. It's also necessary. But when we lean so hard into the plan, we seem to forget all the things we didn't think of, or could never possibly control.
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