Cities

Cities are the platforms we build our lives on. The physical and social infrastructure around us determine what we can do in our lives. When that infrastructure is built well, it can enable us to do amazing things; when it is not, it can constraint us in ways that we might not even see, like fish in water.

Understanding how cities develop is important so that we can play a part in shaping them in ways that intern shape us the way we want. There's a famous quote that says "we shape our tools, and then our tools shape us"; this is true for our cities as well, so it's important that we build them well.

In 2007, we crossed an important threshold: more than 50% of humans live in cities, and the United Nations projects that number will rise to 70% by 2050. We’re now an urban species, so it’s important that we get cities right.

There are a few key schools of thought on what the goal of a city actually is. These are not necessarily in conflict with each other, but they focus on and prioritize different aspects of a city:

• To make things more efficient. People will often talk about "15 minute cities" and trying to find ways for people to not have to leave their small bubble of life. Urban planners will tend to see cities through the lens of how the street networks are laid out, how the transportation system works, etc.
• To maximize human potential. People with this worldview tend to be the urban economists who see cities through the lens of labor markets; for example Alain Bertaud argues focuses on how cities connect people to maximize job access and employee availability.
• To reflect the greatness of their society. Some cities are built as monuments to a country or an ideology. For example, Brasilia, the capital of Brazil, was designed to embody modernist ideals and national progress.
• To reduce our environmental footprint. People who live in cities use far fewer resources than people who live in more dispersed communities. At first blush it is unintuitive, but someone who lives in an apartment in Manhattan has a much smaller carbon footprint than someone who lives on a farm in rural Idaho. They of course use a lot less land as well; if all Americans lived at Manhattan’s density — approximately 73,000 people per square mile — the entire U.S. population could fit into roughly 4,590 square miles, slightly smaller than the size of Connecticut. Given the U.S. land area of about 3.8 million square miles , this would preserve 99.87% of the country’s land.
• To create an asset that generates returns for investors. We can’t talk about cities without talking about the business of real estate, which turns location into a product that can be bought, sold, and rented. There are more people professionally thinking about cities in terms of real estate than probably all of the other categories combined!

• Do new planned cities ‘work’? What’s the case for, case against.
• Can existing cities turn around/get better over time? Case studies, where to look/read.
• What externalities are appropriate to control and regulate, and what externalities are not? For example Singapore famously banned chewing gum because it kept coming up the seats on their metro system.
• Local control versus regional or state level control; a related issue is how much community input is appropriate?
• What should cities learn from other regions and countries?
• What questions should cities and regions get to decide for themselves, and what decisions should be coordinated at a higher level of government? What do we gain or lose as we shift the decision making from one layer to the next?
• How should cities incorporate input from people who do not live and vote in the city but who may live nearby or whose lives are affected by the decisions those cities make?

• It's definitely important to travel to many different cities, because sometimes you don't realize that something that we do in your hometown or your home country is a choice that somebody made a long time ago and just a result of past dependence. For example, in Tokyo there is almost no on street parking; if you have a car, you have to find private parking on your own, just like any other personal item you might want to store.
• I recommend talking to other people about their experience in cities as well. Different people experience cities in very different ways. For example a new parent who walks around with a stroller a lot of the time will notice when there are no curb cuts in the sidewalk at a rate that you may not notice. Or an older person with health issues may notice that the health infrastructure in the community is worse than it should be.
• One method that I like for exploring a new city is to pick a point in the center and then walk roughly straight in one direction for a long time. This is a great way of getting a cross-section of the city and seeing how it evolves and flows over space. (This is not advised in all cities though, sometimes it will take you through dangerous neighborhoods that you might want to avoid.)
• When traveling in other cities, I recommend trying to do some errands while you are there, which will give you a more realistic sense of what it's like to actually live in that city, compared to the typical tourist schedule of eating at restaurants and seeing the sites. Though of course that is fine too if that is what you are into!

• Book: Triumph of the City: How Our Greatest Invention Makes Us Richer, Smarter, Greener, Healthier, and Happier, by Ed Glaeser
• Blog post: America's Growth Ponzi Scheme, by Charles Marohn — America’s pattern of suburban growth depends on constant expansion, creating more costs than revenue over time. At some point, the bill is going to come due.
• Article: An introduction to Georgism, by Lars Doucet — The core idea of Georgism is that "non-produced assets" (such as land and other natural resources) should be treated differently than labor or capital, and that the fact we treat them like capital is the source of many societal problems.
• Paper: Housing Constraints and Spatial Misallocation, by Chang-Tai Hsieh and Enrico Moretti — By limiting worker mobility, strict housing rules in top U.S. cities have cost the economy 36% growth since 1964.
• TV show: The Imagineering Story — A documentary about the creation of Disneyland. One of the most inspiring pieces of media I’ve ever seen.

The resources that have been most impactful in shaping my views on cities:

Triumph of the City: How Our Greatest Invention Makes Us Richer, Smarter, Greener, Healthier, & Happier — Ed Glaeser
Reason to read this: A core part of the urbanism canon. People refer to this book all the time, even if they don't realize it, so it's worth having this as a base when coming into a conversation. (Jane Jacobs' Death and Life also falls into this category, though it's less propagandistic than Triumph.)

This book is about how "cities magnify humanity’s strengths". It's city propaganda at its finest, and I say that lovingly... I clearly fell hard for it! It's hard to not fall in love with cities after reading this.
Triumph is what started me down the path of thinking about agglomeration economies, which has since been a key model for how I think about cities.

Order Without Design — Alain Bertaud
Reason to read this: Offers rigorous yet humble models for how urban systems work. This kind of analytical rigor is incredibly rare in urbanism!

This was one of the best books I read in 2018. My main takeaway: urban planning is still like medieval medicine, with doctors trying to leech out bad humors rather than working off of causal models with predictive power.
I've long been an admirer of Alain's work. I used to be frustrated by how imprecise many urbanists are in their analysis. Then a few years ago, I found a few of Alain's papers. They opened my eyes to the rigor that was possible when talking about cities while maintaining humility that they are complex systems that cannot be fully understood let alone controlled/designed by a few bureaucrats.

Coming from a computer science background, it was satisfying to see the intuitions I'd formed from wandering cities on foot formalized in such an elegant, rigorous way. Instead of using fluffy words like "sustainable" or "livable", you actually had predictive models! His work was so refreshing.

Needless to say, I was thrilled when a friend told me that this book was coming out last year. I purchased it immediately and was not disappointed. I consumed it over the course of a week or so, to the dismay of my partner's family with whom I was ostensibly spending the holidays.

Order Without Design was so rich and full of insight that I'm currently going back and transcribing all of the notes I took in the margins. The book formalized several things I already understood on an intuitive level, and more importantly it challenged several core beliefs I've held for a while about ideal transport modes.

Walkable City: How Downtown Can Save America, One Step at a Time — Jeff Speck
Reason to read this: To examine a specific characteristic of cities and gain concrete ideas for how to improve them on that dimension.

The core argument is that a walkable city is not just a nice, idealistic notion. Rather, it is a simple, practical-minded solution to a host of complex problems that we face as a society, problems that daily undermine our nation’s economic competitiveness, public welfare, and environmental sustainability.
More thorough notes here: devo.nz/book-notes-walkable-city

Progress & Poverty — Henry George
Reason to read this: Challenge the standard poles of political economy that you've likely heard for your entire life, a.k.a. capitalism vs socialism or communism. "Georgism" offers a third, entirely different way to see economics, which helped me break out of rigid patterns of thought.

This book transformed the way I think about land use, monopolies, and value creation incentives. Most people who talk about Henry George focus way too much on his Single Tax proposal rather than the underlying models he puts forward. There are many ways to achieve the goals he describes.
I recommend the modernized, abridged version. The original prose is way too flowery, though if you're into sermons you might like it.

If you want an even more concise (but much weirder) take on George's ideas, I recommend Becoming the Trashcan of Ideology written by a friend of mine who I think wants to stay anonymous. Must warn you that it may not make sense unless you're already familiar with Henry George's ideas...

The History of Future Cities — Daniel Brook
Reason to read this: Gain a sense of romance of the history behind 4 global cities. Ideal if you're about to travel to one of them. (Note: by "romance" I probably mean something very different from what most people mean...)

The book explores four cities—Bombay, St Petersburg, Shanghai, and Dubai—that were created with the idea of being a window to the future in an undeveloped, non-globalized country. Each one catapults itself into a different kind of future, but the common theme is a fascinating lens through which to look. This book helped me fall in love with cities (though I have yet to visit any of the four in the book actually!).

Street Design: The Secret to Great Cities & Towns — Victor Dover & John Massengale
Reason to read this: Streets are the majority of the public space, yet their design is generally underappreciated and not well understood. If we improve our streets, the entire public realm will improve.

The book analyzes dozens of streets worldwide, identifying elements that contribute to their success, such as walkability, flow, aesthetic appeal, and community engagement. They provide guidance on designing new streets and retrofitting existing ones to foster vibrant, pedestrian-friendly spaces.

Seeing Like a State — James C. Scott
Reason to read this: Anyone who designs complex systems should read this to understand the types of problems that tend to arise when we impose rigid, top-down solutions.

This book examines how governments implement large-scale schemes to improve society, often leading to unintended, adverse outcomes. Scott introduces the concept of “legibility,” where states simplify complex local practices into standardized formats to enhance control and administration. This process can overlook the nuanced, practical knowledge—termed “metis”—that communities develop over time. By analyzing historical examples such as Soviet collectivization, the construction of Brasília, and Tanzania’s villagization, Scott illustrates the failures of top-down planning that disregards local contexts. He argues that successful interventions must integrate local knowledge and practices to avoid the pitfalls of high-modernist ideologies that prioritize centralized, technical solutions over community-based insights

The Power Broker — Robert Caro
Reason to read this: Understand one man's impressive wielding of power from a position that was not intended to have it. Also learn about how NYC became the city it is today. Next time you're in NYC you won't be able to walk more than a few blocks before catching Moses' name on some plaque or carved into a building.

It is the biography of Robert Moses, who was the NYC Parks Commissioner from the 1920s through the 1960s. Moses is more responsible for reshaping the entire face of New York City than any other individual, and his thinking influenced urban planners nationwide and beyond throughout the 20th century. Over the course of his career, Moses personally conceived and completed projects costing 27 billion dollars, more than any other US government employee ever. These projects ranged from highways and bridges to housing complexes and city parks, many of which required bulldozing entire neighborhoods and in turn displacing hundreds of thousands of NYC residents. Despite the immense impact he's had on the field of urban planning, Moses was never elected to public office.
The book is not only a look into Moses' fascinating life but also a unique perspective on American history and urban planning during that half century. It's also a must-read for anyone interested in how power works, even if they aren't specifically drawn in by the cities angle.

Aside from the intensity of the story itself, the research that went into this masterpiece is just awe-inspiring. The author Robert Caro is the best researcher-writer whose work I have ever read. His exhaustive series on LBJ is also fantastic. Although the LBJ books are more well-known and even more ridiculously in-depth than The Power Broker, I enjoyed the story about Moses a bit more because his impact was more concrete and on a more understandable scale. Also, The Power Broker is a story about taking a seemingly insignificant position and wielding it in a way that massively amplifies its power, whereas LBJ's story is more about climbing the ladder until you're at the top. As a side note, the narrator for the Audible recording is fantastic.

Crabgrass Frontier: The Suburbanization of the United States — K. T. Jackson
Reason to read this: To learn how and why the form of development has changed over the course of US history.

Crabgrass is a history of suburbanization and the history of federal policy since World War II. It filled in a lot of gaps in my knowledge about how US development happened, answering many questions about the path dependence that got us to some of the weird, contradictory positions we find ourselves in today as far as urban policy goes.
"A sweeping history of suburban sprawl that showed how interstate highway construction, mortgage subsidies, and tax breaks conspired to de-urbanize the country, making the United States unlike anywhere else in the world." — Daniela Blei in A Tale of Two Cities

The Death & Life of Great American Cities — Jane Jacobs
Reason to read this: This book has to be part of any urbanist cannon. It really gives you the texture of the city, and I love that it’s written from the perspective of a woman and a mother.

This classic book argues for lively, mixed-use neighborhoods and thriving street life, pushing back against the urban planning trends of the 1950s and 1960s. Jacobs highlights how cities really work—through vibrant communities, diversity, and small-scale interactions—rather than grand plans and zoning.

From Third World to First: The Singapore Story: 1965-2000 — Lee Kuan Yew
Reason to read this: A firsthand look at leadership and problem-solving on a national scale, from someone who built a country from scratch.

The founding president of Singapore tells the story of how he led his country from a small, struggling colony to one of the world’s richest nations. He shares his decisions, struggles, and vision for building a successful, independent country.

Real Estate Finance and Investments: Risks and Opportunities – Peter Linneman
Reason to read this: If you want to learn the numbers and strategies behind real estate deals, this is a great place to start. This is the nuts and bolts of how cities get built.

This book explains the basics of real estate finance and investment in a clear, practical way. It covers how to value properties, analyze investments, and understand the real estate market.

People and projects to follow:

• First, I’d be remiss if I didn’t talk about my own project — I’m building a new village called Esmeralda 90 minutes north of San Francisco: esmeralda.org
• Las Catalinas – A beachfront village on Costa Rica’s Pacific coast, which has the charm and walkability of historic European villages, despite being established less than 20 years ago
• Coby Lefkowitz – Building Optimism – Community developer and optimist about the potential of cities to solve societal challenges
• Wrath of Gnon – Promotes traditional urbanism, craftsmanship, and timeless design principles in city building
• California Forever is building a new city halfway between San Francisco and Sacramento
• Austin Tunnell – Building Culture – Focused on creating culturally rich, small-scale developments with an emphasis on high quality masonry
• Brian Potter – Construction Physics – Writes thoughtfully about the science and economics behind construction and how to make building more efficient
• Ryan Johnson – Culdesac – Building America’s first car-free neighborhood in generations in Tempe, Arizona
• Charles Marohn – Strong Towns – Advocates for financially resilient cities by promoting incremental development and reducing car dependency
• Utah City – A planned new city project in Utah aiming to blend traditional urbanism with modern sustainability practices
• Casey Roloff – Seabrook, WA – Founder of a walkable coastal town in Washington known for its New Urbanist design and vibrant community
• Vince Graham & Geoff Graham – I’On, SC – Developers of I’On, a New Urbanist neighborhood in South Carolina that emphasizes charm and community
• Brad Hargreaves – Thesis Driven – Explores emerging trends shaping the built environment and urban living
• National Town Builders Association: The National Town Builders Association (NTBA) is a peer-to-peer organization dedicated to supporting builders creating traditional neighborhoods and town centers that embody New Urbanist principles. Through biannual roundtable events, members share best practices, insights, and experiences to enhance the quality and sustainability of town building projects. The NTBA fosters a collaborative environment where professionals can learn from one another to advance the development of economically, socially, and environmentally sustainable communities.