Get Unstuck With a Heartbreak Portfolio

Let your story make your plans for you.

I feel like I’ve become a much more patient person in the last year.

I’ve started to fall in love with the process of things rather than just the outcome. My sense of urgency has shifted from wanting things finished already to wanting to simply put the ball in play.

That’s allowed me to begin shifting my dreaming into planning and doing. This newsletter is byproduct of that.

But the next challenge is how to start having a tangible and significant impact on the built environment. “How do you become a developer?” is one part of that challenge, but the other part is figuring out where to even start.

I’ve felt torn in several directions: perhaps I go back to my hometown and invest there? Maybe I commit entirely to where I live currently in Spring Hill, Tennessee.

But neither of those answers felt right or satisfying, because several other places have tugged at my heart. Several other cities have been a part of my story.

That’s why I’ve put together a Heartbreak Portfolio: a collection of places that have deeply shaped my life as a whole and as an aspiring citybuilder. Places I have personally lived in, wept over, and dreamed for.

The first place that went on that list was Baltimore, Maryland. It was the place my heart broke on two separate occasions - both exiting MT&T Bank Stadium - some nine years apart, as I saw homeless men out in the cold with no one to help them. The second one was out in the snow. I wasn’t able to help then, but I want to help now.

I’ve dreamed of buying this property and turning it around for six years. (Columbia, MO)

The second place is Columbia, Missouri, where I went to college, and where wrote about last week. There’s two blocks that particularly have my heart and sit just north of downtown. Within walking distance of a high school, there’s several payday loan shops and a strip joint, among other things. The city’s trying to turn things around, and my church built a pop-up park in the neighborhood about three years ago. I want to finish what we started and make “The Loop” a place of flourishing.

There are a few places on my list (including where I live), but I’ll save those stories for another time. (I share a bit about Spring Hill here.)

I don’t know where I’m going to start, but having a few cities and areas of cities identified has made things far easier than browsing the entire country on Loopnet. It’s allowed me to start asking the right questions about projects. And it's helped me channel my heart for these places into motivation to do the work and get to a point where a project is underway.

Whether you’re an aspiring developer, tactical urbanist, storyteller, or something else, getting started can feel incredibly overwhelming. Reading stories about struggling city after struggling city can tug you in a thousand different directions for a million different causes.

Building a heartbreak portfolio helps you cut through the noise and identify places and problems you are uniquely equipped to tackle. It allows you to sort out what is merely “interesting” from what’s struck a chord deep within your soul. It helps you find truth north.

The beauty of patience is that it allows you to pick more than one place, because it doesn’t all have to happen right away. You can put away all the perfectionism and anxiety that surrounds the “decision.”

So if you feel stuck like I did, start with a simple question:

Where has made you weep? What about it? What do you wish was different? What sunk deep enough that it formed you in some way?

Write it all down, circle the smallest (most accomplishable) thing on the list, and get working.