On Cities & Building A Scene

The most interesting thing about living off-the-beaten path, is realizing that most people living in those places have some kind of tie to the smaller life. Whether it’s a family connection, a relationship or just a desire to “get away from it all,” I’ve encountered all types of folks with stories of their own on what motivates them away from “the big city.”

Yet, many of the narratives I hear from people building medium-sized cities like Bloomington (Indiana) where I live, revolves around startups, creating energy where it doesn’t currently exist and enticing 1) people who are here to stay and create jobs through some magic or 2) bringing capital (and people) from elsewhere to make our already good place a bit better.

Ignoring all of the challenges that comes with, I’ll just say that the most difficult part of building a scene is how much work goes into cleaning a particular corner of the sky. It can be vast, unnerving and frankly, a lot of patience. Most people seem able to invest in one or two pet causes and are happy with that. I find myself shocking close to the cauldrons of influence on one hand, yet often feel as distant from actual change as I’d feel in a larger place.

I like to say the biggest difference between say Brooklyn and a place like Bloomington, is the fact that in Indiana, there’s one of everything. In Brooklyn, I can find multitudes of organizations and overlap, but there’s enough space — somehow — to be involved in a niche or to craft your own lane if you have the right mix of money, time, relationships and whatever magic necessary to pull it off.

This isn’t a screed about why some places are better than others, it’s a reflection on the need for people making decisions about growing communities to be responsive and participating in the scene they’re trying to create. It doesn’t just rely on outsiders or insiders, it’s a mix of the two that combine to forge some kind of strategy that can propel a sleepy town into something better.

Every night, there’s a lot happening relative to a place of this size. Surely, having a Big Ten university helps tips the scales dramatically. The problem is, there are only so many people that you can engage. Students are a unique challenge due to their transient existence and other commitments that make them difficult to count in your total numbers for much of anything. That leaves the relatively small sliver of people who might be worth targeting.

I’ve been wondering aloud if I expended this same level of energy in a bigger place, what would the end result look like? There’s a lot to say for a critical mass. I wouldn’t be the first person to decide I needed something bigger, nor will I be the last. I have always been drawn to relatively small places, because the proximity and lack of pretense at times can give you an outsized ability to make an impact.

But across the board, I find that it’s a lot more difficult to penetrate whatever smallness pervades everything from the local politics to the ways people become close friends. I’m sure a lot of this has to do with dynamics of American life, and are present in other places. I’m quickly getting to a point personally and professionally, where I want to be intentional about what I work on, how I work on it and why. Especially extracurricular/passion projects, because I’m one of those people with lots of ideas and often feel like I’m “running out of time” to clear my own docket.


Reflecting on a digital footprint

For the past week, I’ve been doing this thing where I read old posts. Not old posts on work things, but personal blog posts. Across the web, like a virtual office strewn with coffee ringed papers, I have content I’ve been saving for myself off and on. A lot of these breadcrumbs were not written deliberately for me to revisit, I simply wrote them at the time because it’s how I felt. I don’t do much of this anymore, because it seems passé to write longform blog posts ranting your feelings.

What’s been interesting about going back and revisiting the past, is the assurance I take from understanding my journey at the time and what was ahead of me. It feels like a long time ago and at the same time, it feels very recent. Thinking about that context, makes me start to realize that the next 4-5 years will look and perhaps feel very different than what life right now feels like.

It’s easy in the midst of frustrations, to feel like things are permanent. Getting a sense of perspective is especially difficult when you move a lot, because the people in your world only have a sense of your immediate life and not the roads you took to get where you are now. Lately, I’ve been thinking a lot of about mindfulness and arranging my life in ways to stay present with what’s happening now.

Going back and reading my archives has helped immensely, because it allows me a chance to reflect on thins that no one else would know. I can conjure memories of complexities and thinking aloud how I would get from whatever space I was in, to the next stage of my life. I can recall often feeling marooned and plain-old stuck. Reminding myself to be grateful for the progress and the process has been instructive.

1. Curbing my social media usage

The post-Trump world of Twitter is surely a mental drain. I just haven’t been as engaged to participate. Not only about politics, just about anything really. I can recall feeling like for a long time, the only true friends I had were living in other places and I’d use the web as an excuse to communicate with them since it didn’t feel like at times the people in my everyday life really “got” me. I realized over time, the problem wasn’t the people, it was me.

Cutting back my usage has been helpful, though I backslide. Instead of feeling like I need to post a photo everytime something happens, I’ll sometimes take a picture and record it later. I’m also more judicious about what I share. For a long time, I didn’t really have much to post about, so I think there was a long period of time where I felt really good to have things to share and would share EVERYTHING. I’m over it, now.

2. Please Remember Rule #6

Don’t take yourself so seriously.

3. Defining discipline for yourself

Maybe it’s the fact that I spent four years in the Air Force that makes me view the idea of “discipline” as something hard-faced, stoic and downright painful. In reflecting on my challenges with the notion of discipline, I’ve had to interpret my own notions of what discipline means for me and how to configure a life where discipline dictates the parameters of things I’ll do and won’t do. For instance, I’ve never been drunk. It’s not because I want a medal for it, I just can’t bring myself to drink anything to excess. That’d discipline, but I never thought of it that way before.

4. Being a contribution

Instead of spending days wondering precisely what will happen, I approach days with a question, “How Will I Be A Contribution Today?” I’ve long been mindful of contributing, I’d just never put it into those terms before.

Reflecting has brought me full circle with my past. I think there’s still a strong element of figuring out where the future leads and how to trudge that road. But knowing how you got where you are, has a lot of value for orienteering your way to the next port.

Doing your own year in review slidedeck

2016 was an interesting year for me.

It’s easy when you set goals, to lose sight of the things that went well to focus on the things you’d wish had gone better. I was talking to a friend about his own work and he mentioned doing an annual review that was just for his partner, because he’s independent. I think it’s a fascinating idea to assess your own work over the year — your successes, what didn’t go right — and develop a roadmap for the upcoming year. Even if it’s only internal (e.g. just for you), it can be a powerful way to focus yourself on the things you deemed important and to take stock of your successes.

Rather than overthink every thing you did, I spent time just highlighting big things that happened through the months. You can pick and choose — after all, it’s your review — but again, the goal at the end is to feel good about what you accomplished and if you didn’t do enough, taking stock on each month and how to be proactive in the new year.

Did you do an annual review of your year? Which ways to do you take stock of your work?

I’d share my template with you, but part of this exercise is about sharing what you’ve done internally and not feeling the need to itemize for the crowd. It’s less about showing off (though if you contact me offline, I’d probably send it to you…) and more about taking stock and re-assessing what the next steps are going to be.

Happy planning!


Root, Root For The Home Team


Anyone who knows me well, is aware I’ve lived a lot of places. Almost all of these moves have been some combination of work-based or relationship-based relocations.

One of the challenges of pulling up stakes and relocating is cultivating networks. Since my formative years, I’ve always been involved in civic projects. Not every community is tailor-made for an outsider to show up and participate in substantive ways on issues that might be related to policy and/or innovation.

As a result, I’ve spent a lot of time trying to figure out where I fit. Without the connective tissue to keep you rooted in a place, all you have is work and whatever relationships you cultivate on your own. These foundations are not always built strong enough to maintain life in a small place, especially if you’re upwardly mobile and have broader networks in bigger places.

So what’s a peripatetic person to do? This post isn’t prescriptive, it’s reflective of my own path. At the moment, I’m doing what I always do. I try to figure out ways to meld my entrepreneurial goals with whatever established activities are already going on wherever I am. My goal is to get in where I can, but resources matter, as do having the infrastructure and a team to execute big ideas and goals.

I feel like there is a lot we can do, when we’re focusing on our own contributions and let people know we exist. It’s easy to sit at home and expect that opportunities are just supposed to come to you. But most people don’t know the talent embedded in their own communities. While it’s great to create activities to engage and ignite interest, the reality is, we sometimes have to raise our voices and let people know we’re here and what we’d like to do.

Critical mass is important, but so is working within the confines of what your circumstances are as a person or a community.

On Representation


I never thought much  about growing up in a place where black people played tennis. It just happened that my hometown happened to have the best public tennis facility in our area, so much that people from suburban areas would flock to our courts to play and practice with coaches our in town.

I think a lot about this, because I realized when I was in my late 20s that growing up where I did probably shaped much of my worldview in ways that being someplace else might not have. I’m not saying it was all perfect, it was far from that. But just the access to influences who didn’t just look like me, but who were a melange of characters who demanded excellence in different ways, helped shape my perspective because I wasn’t a stranger to black excellence. Not only that, it never occurred to me that there were jobs or things off-limits to me because growing up I saw black people who did everything. My first doctor was black, all of my school principals except one were black — my first elementary school principal was a black woman for 5 of the 6 years I was in that school.

Even the white teachers I had seemed to be hellbent on teaching us in ways that defied conventional expectations. We were reading Orwell in elementary school. We participated in activities like Odyssey of The Mind that took us away from our town and around the state and region to compete — and succeed at high levels.  When I lived  in distant places years later, it occurred to me at different times there were people who simply had never encountered a black person in a leadership position. Or a black dude who was the tech guy and not the basketball coach. I joke about this sometimes, but it really does matter. How people see  you doesn’t just affect how they treat you, it impacts the range of opportunities you’re offered and the ways people perceive your smarts because  they’re not quite sure how you got where you are — since they’ve never seen anyone doing what you’re doing.

That’s not my problem, though. And yet, it becomes my problem more often than now. It doesn’t excuse being less than excellent. Make no mistake, I’ve been afforded some fantastic mentors and people throughout my adult life who have seen things in me I had not yet seen in myself. They’ve supported my goals, encouraged me and tried to connect me to bigger and better things. Almost none of them looked anything like the people I grew up with.

I just felt the need to connect the dots on representation. I know some people look at “firsts” in 2016 and think even the mention of such things is a step backwards. “Why does it matter?” “Why can’t we just celebrate these accomplishments as Americans?” We can, but there’s an added joy to defying expectations, especially when there are structural barriers to many of the things that people still want to do today. Remember that successful might happen globally or nationally, but it starts locally.

Think of bridge trolls as gatekeepers. Every time you want to do something, there might be one person to determine whether you get to do it or not. Sure, you can go to another town but that takes time and money. Or find a private club that’ll accept you. Maybe it’s just finding someone who sees your ability and talent and is willing to nurture it. Success is measured in small distances, not big gaps, especially at the elite level. What separates the people who make it, is often a matter of timing and opportunity.

Whenever there’s some historic achievement where someone is mentioned to be the “first” to do something — specifically here in America — I often vacillate between being annoyed that we have to mention it and grateful that we live in a time where such barriers are falling.

I try to reflect on every moment  as if it’s penance to the people who  were denied access, who fought and broke rules and raised hell to give their forebears access to the opportunities they now enjoy freely.

Every time you hear “so and so is the first _____ to do _____,” it’s a little whisper of apology from every single person who might not have been complicit, but part of the collective debt we all share from a past with fingerprints all over our lives today and how we live them.

Designing a better city

On design & policy. Have you ever noticed how small the print is on subway ticket purchasing machines? How often do you think about the hundreds of touchpoints throughout your day that comprise whether you go home feeling like you had a good day or not? Every part of the experience of your interaction with the communities where we live and work are design decisions made by someone faceless. The choice could have been the result of a series of meetings 95 years ago or a change made last week. We rarely know the difference.

I’ve been thinking a lot about the intersection of tech, marketing and just digital strategy as a whole. People like me spend a lot of time in offices and within entities using brainpower to ultimately figure out how to sell more widgets. Maybe those widgets are enrolling more college students or selling more sneakers or helping a brand humanize itself to stakeholders. 

Along the way, I’ve spent a lot of time pondering ways to be a broader contributor to real problems that we face in communities across the country, but wasn’t precisely sure how to fuse together the design and tech parts with policy.

Being new to a city is a special kind of hell. Unless you already have familiarity with the place you’re moving to or have some other connection (work, relationship or family) that can bridge you from ‘stranger’ to ‘part of the tribe’ it can take years to on-board your way through the morass of written and unwritten ways that our communities are designed to thwart outsiders. Not all of this deliberate, but these challenges have real impacts.

Every place is different. For every community that’s hostile to outsiders, there are others desperate for an injection of interest from afar.

With the increasing number of quasi-governmental projects springing up that want to figure out how to bring tech innovation to government, I’ve been contemplating how to use design as a tool to expand our vocabulary and imagination about the future of our communities.

Here’s the thing, I’m not as interested in whether we can create tech solutions to structural problems. If building a better website or doing user research to solve a community problem like access to summer meals for kids or helping making paying utility bills more efficient, then I’m all for figuring out the ways that tech can help us.

What if we could use the tools, frameworks and vocabulary of design to inform policy? Ideas are important, but only when they lead to impact. We need entities that help policymakers, stakeholders and citizens work together, engage and collaborate to solve problems. 

Strategic Design is a discipline that comes to us from Finland and it’s mostly concerned with solving big structural problems that cities, governments and organizations face. 

“Strategic design has a set of direction, over and above being a set of tools, a vocabulary and a series of projects. Its focus is in enabling systemic change through re-shaped cultures of public decision-making at the individual and institutional levels, applied to the primary problems of 21st century governance.” — Dan Hill, Dark Matter and Trojan Horses

While we already have wonderful folks at places like Code for America, 18F and the US Digital Service, what I’m talking about is far broader than tech conversations. Lately, the folks at Y Combinator have decided they want to tackle these issues too. 

I am sincere in my belief that the frameworks and vocabulary of strategic design can help advance our communities forward, by helping us think broadly about how we create barriers to progress for ordinary citizens everyday. 

Here’s how we move forward: Assembling an interdisciplinary group of doers. I’m calling this thing Design of the City. Designers, strategists and people in-between are welcome on this journey. I imagine at first there will be a few of us, but once we figure out what we’re doing, we’ll expand rapidly.
Engage with governments, non-governmental organizations, civic groups and even companies to view high-level challenges and use design tactics and processes to consider the aspects of these problems and develop solutions.
By engaging with an outside group of stakeholders who become embedded within the entity for a set period of time, we’re able to move quicker to begin diagnosing the challenges with traction. I don’t think this prevents the barriers that impede in-house solutions, but the fresh sets of eyes can be vital. 

I believe there are people who want to do more than just build products, we want to construct communities, services & structures that serve populations for the next hundred years. Much like the physical infrastructure of many cities, we have a policy and governance framework bequeathed to us from forebears that could not have imagine the distances we’d travel. We need to reflect and imagine a new set of rules, frameworks and invoke an imagination that allows to envision communities as vibrant and flexible. 

Incoherent thoughts on exploration


I’ve always been an explorer.

In a world where it’s often a lot easier to join something prefabricated, I’ve consistently taken the harder road towards building something of my own. One summer between my 7th and 8th grade year, I got the bright idea to start a baseball league. Not a team, an entire league.

As you can imagine, I had no idea clue about things like insurance, sponsors or even players. I called the local newspaper and for some reason, they printed my ad for players and for weeks, people from all over Central Jersey started calling my parents house about this baseball league. Whenever someone proposed a new challenge, I’d explore ways to solve it. From . insurance to sponsors, I talked my way into partnerships and alliances from grown adults who did not question my moxie.

As all good things do, the experiment only lasted a few weeks. I didn’t have enough players because who in their right mind lets a thirteen year old organize a baseball league with a straight face? But it was an interesting few weeks nonetheless.

That was only the first experiment.

With this path comes all of the inevitable challenges of trying to make a way out of nothing. What’s more difficult is getting to the point of realizing there’s only so much you can do by yourself. I don’t realize at the time how difficult the road is.

Whether it’s a conference or a shoe brand (both things I’ve done) or thinking about my own work trajectory and the future, I spend a lot of time contemplating what the so-called right way is. I’ve met enough smart people in my life, with life paths I’ve admired to know that there is no prototype to the canvas we paint on. We just start working and fill in the gaps as we go. Sometimes, you start over entirely. Except, there’s no such thing as truly starting from scratch.

It’s so alluring at a certain point to believe that you have to put on the armor of being a know-it-all, because we reward it. At least in America, anyway. You sit in meetings and these days, turn on the TV and watch people talk outside the side of their mouths with the faintest regard for whether anything they are saying really meshes with reality.

It’s frustrating to think that’s the way you’re supposed to get ahead. I’ve always favored a path, especially in recent years, of an earnest recognition of what I do not knowEmbracing the fuzziness makes me feel like I’ll get closer to answers I didn’t imagine, because I concede the things I’d like to learn more about. Probably not a winning strategy for proving you’re the smartest person there ever was, but that’s never been something I’ve wanted anyway.

So much of the challenge of knowing where you fit is assembling the right puzzle pieces for a life that makes you want to get up everyday poised to add more pieces. At least, that’s the formula in my head. As I get older, I keep feeling like it’s supposed to make more sense and the opposite ends up being true.

Much like playing an easy board game, you know where all of the pieces go and how they’re supposed to work. I just find that winning is harder and harder even as I’m better prepared than ever to play.

Perhaps it’s just being sure of the game you’re playing in the first place?