Alex Bozikovic of the Globe and Mail recently made a good point in one of his articles about how challenging it is to properly “placemake” when it comes to large-scale masterplanned projects. This blog post is not at all intended as a commentary on any one project, but I would like to acknowledge that, for a variety of reasons, places do often need time, layers of history, and some patina on them in order to really settle in. When you build big, it can be easy for things to end up feeling sterile.

It is also true that tastes can change over time (as we have talked about before), though you could argue that this change is driven by the settling in process. Spaces start to get rethought, reconfigured and recast, and that can make them more desirable.

But it’s not just about time. What else is going on here that makes masterplanning so tricky? Four things immediately come to mind. If you have any others, please share them in the comment section below.

One, a lot of the old stuff that we love is now illegal and no longer possible. Here is a great example from Paris that I wrote about. But there are countless others. Another example from Toronto might be the corner retail stores that used to dot our residential neighborhoods. In my opinion, these are wonderful additions. They create urban vibrancy. But today they are generally legal non-conforming uses.

Two, great urban experiences often happen at the micro scale. Things like the perfect patio with a great view of the street and full afternoon sun. Or that intimate side street lined with beautiful homes. These are some of the moments that make cities great. But when you’re masterplanning at the master scale, it is perhaps easier for more of these intimate details to get lost.

Three, any new community needs to be seeded. Cities and communities are nothing without people. And so what will be the anchors? What will bring people here? How are we going to animate its streets and public spaces? These can be tricky problems to solve and they often take time (and density).

Four, masterplanning likely equals fewer feedback loops. I recently came across this great line from Chris Dixon: “Composability is to software as compounding interest is to finance.” Composability is the ability to mix and match software components. And the idea here is that open source software allows new software to get built on top of existing stuff (just like interest on top of interest). This way the world never needs to solve a problem twice.

I’m not sure what the pithy line should be for city building, but cities also compound. We are constantly building on top of the efforts of others, except when we’re largely not, and we’re designing a whole bunch of new stuff all at once, as is typically the case with masterplanned projects. This isn’t inherently wrong, but building a community from scratch will always be more difficult than adding on to one that is already successful.