“Make no little plans. They have no magic to stir men’s blood and probably themselves will not be realized. Make big plans; aim high in hope and work, remembering that a noble, logical diagram once recorded will never die, but long after we are gone will be a living thing, asserting itself with ever-growing insistency. Remember that our sons and grandsons are going to do things that would stagger us. Let your watchword be order and your beacon beauty. Think big.”

-Daniel Burnham, Chicago architect. (1846-1912)

I’m a big fan of Chicago. Having now visited the city, I can say that everyone was right when they told me that I was going to love it. It has great art and architecture, great food (with some of the largest portions I’ve ever seen), great nightlife, and great people. 

But I don’t want to talk about any of these things today. Instead, I want to talk about something much more specific that stood out to me last weekend: Chicago’s relationship to both the water and the street.

While Chicago and my hometown of Toronto share many similarities– including being situated on a Great Lake and having rivers flow through the middle of them–the relationship to these bodies of water is remarkably different. Here is a photo of people kayaking in the Chicago River on a Friday afternoon:

What impressed me about Chicago is how intimate and urban the relationship is with the lake and its rivers. If you look at the photo above, you’ll see that many of the buildings are built right up against the river, but that there’s space allocated for riverwalks, patios, and so on. It’s all about engaging and connecting with the water.

Toronto on the other hand, is only recently starting to reacquaint itself with its bodies of water. We spent much of the second half of the 20th century with our back turned to the lake and without a strong urban connection to the Don River. And if I had to guess why it’s because we built highways along them.

We built the Gardiner Expressway adjacent to Lake Ontario and we built the Don Valley Parkway adjacent to the Don River. This fundamentally changed our orientation and largely precluded us, I think, from creating the same kind of waterside urbanity offered in Chicago.

As an example, consider that in the first half of the 20th century, Toronto’s Parkdale neighborhood – which today still has a questionable reputation – was actually an affluent and desirable waterfront community filled with beautiful Victorian mansions. It was well connected to the waterfront, and so the area flourished. Here’s what Sunnyside Pavilion used to look like:

But then in the 1950s we built the Gardiner Expressway, disconnecting Parkdale from the lakefront and destroying many of its amenities, such as the Sunnyside Amusement Park. In turn, the rich people left and their large Victorian mansions got chopped up into rooming houses and other rental housing stock. And in my view, Parkdale still hasn’t fully recovered from this. 

Highways are divisive. There’s no question.

So unless you can afford to bury them, it comes down to trade offs: Do you want to make it easier for people to drive in from the suburbs or do you want a truly spectacular water or riverfront? In the 1950s we chose the former. But even still today, the thought of tearing down–even a portion of the Gardiner Expressway–is fraught with opposition. I guess not much has changed.

The second way that Chicago impressed me is through the relationship that many of its buildings hold to the street. They come down to ground level with authority and with great retail presence, and often make no amends about their mass and impressiveness. This frames the street and creates a level of urbanity that isn’t always found in Toronto – particularly outside of the downtown core.

In Toronto, the trend today is towards street level podiums, significant setbacks, and delicate point towers that minimize the impact of their height and allow for natural light to reach street level. It’s well-intentioned and perfectly appropriate in many urban settings. But sometimes you need a little urban assertiveness. Sometimes you want to impress and impose. And Chicago does that.

What I’m getting at is that Chicago architect Daniel Burnham was on to something. He famously advocated for man (that was the era) to think big. Make no little plans, he said. And it’s admirable advice. Toronto is going through a tremendous transformation right now. We’re North America’s boomtown, which is a title that Chicago would have held at one point.

But as we build for the future, let’s remember that, long after we’re gone, we’re going to be judged based on the plans we are making today. So why not make them big ones.

I’m flying out to Chicago this morning, and so I don’t have a lot of time to write. But I am taking my iPad with me and I plan to continue writing every day that I’m there. As some of you might remember, I’ve never been to Chicago before. This will be my first time. So I’m expecting lots of writing inspiration.

That said, I’m going for a bachelor party and so I may not get the chance to geek out about the city as much as I normally would. There certainly won’t be any any Frank Lloyd Wright pilgrimages taking place. However, I have convinced the group that the architecture boat cruise will be a great way to see the city and a nice way to start off the day following a late night.

If you’re from Chicago (or just know the city well) and have some must-see recommendations, I’d love to hear from you in the comment section below. I’m excited to visit Chicago because it’s another Great Lakes city and I’m told it’s somewhat similar to Toronto. It’ll be interesting to see how they compare and differ.

This post originally appeared on the Rotman Morning & Evening MBA blog. 

As a recent graduate of Rotman’s Morning MBA program (and presumably because somebody over there reads Architect This City), I was asked to write a guest post for their MBA blog. More specifically, I was asked to share my thoughts on the real estate industry and on my time at Rotman. And since I haven’t really done a post like this before, I thought it would be worthwhile to do.

But before I begin, I think it’s important to explain a bit about my background and my motivations for doing an MBA in the first place. Before going to Rotman, my first master’s degree was in architecture and real estate from the University of Pennsylvania. Basically it was a Master of Architecture combined with their MBA real estate concentration. So it included everything from real estate finance to real estate development.

Having already done this 3-year program, there were a couple of things I wanted out of an MBA program. First of all, I wasn’t prepared to go full-time. Five years out of the workforce was simply too high of an opportunity cost for me and so part-time was all I considered. I also only applied to Rotman because I didn’t want to waste any time traveling outside of the city (or to other parts of the city). I also saw Rotman as a rising star and one of, if not the, best option in Canada.

At the same time, I didn’t give much thought to the real estate curriculum being offered even though I fully planned to stay working in the real estate industry. I felt like I already had that sort of formal training and so, unlike some of my classmates who were looking to switch into real estate, I was after something else. I ended up majoring in Innovation & Entrepreneurship.

What I was trying to do was really round out my skillset and fill in some of the missing holes: accounting, marketing, and so on. But even more importantly, I had drunk the kool-aid around Rotman’s focus on integrative thinking (renamed “business problem solving”) and “design thinking”. And since there will always be a part of me that thinks of itself as a designer, it seemed like the perfect program for me. 

Because at the end of the day, it’s not that hard to learn how to create a real estate development pro forma or calculate your expected exit cap rate on some piece of real estate. That stuff is all fairly mechanical. It might seem quite mythical when you don’t know how to do it, but once you do, you quickly realize that a financial model is only as good as the assumptions you put in. As we’re told in school, garbage in = garbage out.

The real value gets created in the assumptions. It’s created in the way you think about the market, your product, and your customers. And a lot of the time, the most value is created when you know or believe something that nobody else believes to be true. If you’re a lemming, you’re going to get lemming like returns and outcomes. So in a lot of ways, I went to Rotman to help me think better and think differently.

In some industries, resting on your laurels can kill you in a relatively short period of time. See Blackberry. Real estate, on the other hand, is generally a bit slower moving. But that doesn’t mean that change doesn’t happen and that there isn’t room for loads of innovation.

Just look at the Toronto of today versus the Toronto of 10-15 years ago. We’ve transformed ourselves into a city of high-rises where more and more people now want to live in the core of the city. This has brought commercial landlords back to the city center so that employers have downtown office space to attract the best human capital (see South Core) and it’s brought suburban retailers into the core to sell to these same urbanites. We’re seeing a complete reversal of the trends experienced with the last generation.

Amidst all of this, I’ve been noticing a growing awareness and passion around cities. My blog Architect This City started as a forum for architects, planners, and developers, but it has grown into a community of thousands of people who simply love cities. They’re passionate about everything from architecture to grade-separated bike lanes (as geeky as that probably sounds).

So I think that it’s not only the real estate market that’s changing, but also the professions involved with it. I’ve written a lot about the future of the architecture profession because I think we’re starting to see the emergence of new business models. Architects are becoming developers and developers are starting to become much more heavily involved in the shaping of the communities in which they build. Which is why in many ways, I think of my self as a city builder more than anything else.

Finally, to make matters even more complicated, technology is starting to have a huge impact on the business. Zillow.com just bought Trulia.com for $3.5 billion to form a portal that will now serve around ¼ of the online US residential market. And Opendoor.com is getting ready to launch a product that seems entirely poised to disrupt the way homes are bought and sold in America.

So what I’m getting at is that there’s absolutely no guarantee that the way we used to do something, is the way we’re going to continue doing it. In fact, I operate under the assumption that everything can and will be changed by somebody at some point. And if this is the way you approach things, then it should become abundantly clear to you that being able think critically is going to be one of your most important assets.

When I was just starting at Rotman, I met for lunch with an upper year classmate who told me that one of the best things he’s taken away from the program is the ability to think about the way he thinks. That may sound silly to some, but in our uncertain world, it’s actually a great skill to have.