On Cities, Design & Simulations

A few times a year, I will binge on simulator computer games. Whether it’s the latest clone of your favorite SimCity-like game or a game that’ll let me sim hundreds of baseball seasons in a few hours; I find something enjoyable about being able to see the history play out before my eyes in a quick span. 
When it comes to designing cities, things are often too idyllic for the real world. For instance, I don’t ever think to build slums. It doesn’t occur to me where the poor people” live, because I’m too busy worrying about how to raze a particular block to build a stadium akin to real life. While I am complicit in designing a utopia, the game mechanics do not really give you the option of reflecting the world as-is, leaving the human immersing himself (me, in this example) on world building to either imagine a scenario where people in my town do not have access to clean water or where we’ve decided as a community to sell of their public schools to the highest bidder because it makes more financial sense.
I used to worry about sharing too much personal stuff on social media for fear of being deemed less serious. I don’t even tweet many of my articles anymore, because at a certain point, it starts to feel like only the most polished, well-coifed things can be presented for (possible) consumption by a massive few. It’s weird that what used to pass for authenticity now just feels like shouting into one of those abandoned pipes inside a park where you can walk to the other end. Maybe someone will hear you, but chances are, you weren’t loud enough or maybe no one was around when you were shouting.
I’m thinking a lot about innovation, execution and the way we design things. Like many of you, I’ve been thinking a lot about politics. Except, I’m thinking about the everyday challenges that communities face. I care about the sorts of politics that doesn’t make anything other than the local news, because that’s just where my head is. When I have discussions with my friends these days, it’s about the homeless problem in our small city or the glacial pace at which innovation seems to happen, despite so much home and promise.
It’s probably apropos of my generation that we think we have answers to big problems, but the thing about local politics is you can actually go to the board meetings and be heard. You can be involved. Make no mistake, it’s laborious, it doesn’t pay anything and the work is generally anonymous. Nobody will fete you or care too much about it and your gains will be marginal in comparison to the effort expended. 
Nonetheless, I cannot help but believe that what we need are more people rolling up our sleeves to give voice to the issues that confound our own communities, all the while we raise hell about whatever grand problems we hope to solve. I’m a firm believer in being able to be outraged by many things at once.
I’ve been reading a lot about redlining lately. I knew about the federal government complicity in ensuring segregation was maintained during the Post-World War II boom of federally secured home mortgages. What I was not aware of, was how pervasive it was and even instances where well-meaning developers wanted to flout the rules to create integrated housing or at least separate-but-equal housing for non-whites; they were prevented by the Federal Housing Administration from doing so under the guise of maintaining order.
What does any of this have to do with design? As I think listen to pitch after pitch, and people tweet their best ideas, there are a dearth of ideas attempting to solve local problems. Everybody wants to scale the mountain of free” money hoping to kick an idea to the stock market, get rich, cash out and then maybe focus on the things they’re passionate about. For all of the grief we give people who play the lottery, the delusions are a lot more similar, except playing the Powerball results in a bit of daydreaming. Whereas building a startup that you’re convinced will change the world” involves a far grander set of delusions that may or may not jibe with reality.
A lot of folks on Twitter have been asking what the responsibility of a designer is. Contemplating an ethical code is a valuable direction, but I’m more interested in the granularity of our everyday experiences. I want to envision a world where we highlight the people doing the unglamorous tasks that make our everyday lives function. 
Who are the people designing interfaces for grocery store self-checkout machines? What about warning microcopy on the back of industrial machines? I have a bunch of questions about so many systems we take for granted, that our conversations defy this reality unless you have people in your life (as I do) so removed from the world you inhabit away from them, that it forces you to stay grounded. 

On Design, Chaos & The Way Things Are

I’m a student of history. More than that, I’m a student of policy. Before I got distracted with a career in web shenanigans, my path was headed towards a Ph.D. in Policy Studies because I saw that as a way to impact the world. Then tech happened and I started thinking about other things and figured I’d eventually get back to dealing with the world in a better way once I had other stuff figured out.

Well, things aren’t getting better. Despite all of the speaking I do and the cool people I get to interact with and learn from, I often feel like I don’t have anything new to contribute to conversations about code. I find most of our rants — even my own — about design and the ways we can improve the world a bit drab. It’s less about people not caring (I certainly do), but I feel like there’s a need to be more audacious.

When you look at the design of policy matters, everything from health care to housing, it’s evident that a lot of people are asleep at the wheel while the bulk of the country suffers and falls behind because no one really understands how to impact the daily operations of our services. Often, you’ll read about how other countries have tackled these issues through better bureaucracy, homogeneity or a strong social safety net that we in the United States seem to eschew in the ethos of “Sucks for you, I got mine.” 

What a strategist to do? I’m thinking aloud not just about a pivot of my own work, but developing a better toolkit for helping people who feel powerless to shift the way they work to impact the everyday balance of things. While we can’t all go to Washington, there is much work to be done in our own backyards. The U.S. Digital Service and the various innovation outfits that are cropping up throughout California, Austin, Philly and elsewhere are admirable and surely have their place. But most of these well-intentioned entities just reinforce the status quo that tech has a problem with.

I’m tired of hearing about outreach and pipelines. I don’t need to read another screed on Twitter about how [x] company needs to “do better” with the solution generally being “hiring a few high profile people to talk about how this is a complicated problem and things are changing.” We need to stop wanting to work in tech conclaves with likeminded people and need to build new settlements in places nobody really wants to live.

I say that derisively, because if you’ve been to any small city in country, there are always a few dozen diehards who are convinced its the best place in the world and if you spend a few days with them, you’ll start to believe it too. Then you leave, go back to your city with ample food options at 3am and remember why you pay too much for rent because there’s no way you’d want to leave this for that. 

So where does that leave us? Where do we go? How do we solve the dilemma of a bunch of otherwise smart people wasting their 20s trying to raise “venture capital” and “pitching” rich people who seem to get off on watching these kids squirm and waste their time applying energy to problems that don’t solve the core issues of our communities. Even when you live in idyllic Midwestern cities, there are big problems at stake. Homelessness is rampant, Baby Boomers and their progeny benefit from the boom in rental properties while millennials and beyond opt for experiences over owning stuff (other than an iPhone…) and the media struggles to keep up.

Every cool person with an idea can’t go work for the cool companies. And despite what it feels like, we’re all not going to start successful companies with huge market caps either. That doesn’t make the pursuit of solving everyday problems less worthwhile or meaningful. It just means we have to reposition what it means to be useful.

Reclaiming strategic design

The good folks at the Helsinki Design Lab once called ‘strategic design‘ : the application of design principles towards solving big picture real-world problems. This is not sexy because there are no artifacts to put on your portfolio and you can’t sell governments on the trenches when people have elections to win. Which is why we constantly see solutions pointed towards the low-hanging fruit and using an ice pick to chip away at structural problems when we really need a demolition crew to blow up the ways we’re attacking these problems.

Where does this lead? More on that later. In search for myself and deciphering my future, I’ve realizing that I was spending too much time attempting to fit into whatever people are talking about, rather than carving out my own lane and moving towards what interests me. I never stopped caring about these topics; many of my private conversations with friends are about problems local and global and ways we can attack them.

I think there’s more we can do and frankly, we need more voices that don’t reflect the dominant culture participating in shaping the future direction of where we’re headed. We also need to empower people who are quiet, prepare tools to help people level up and educate folks who don’t know how we got here about the ways we ensure that our next generations don’t have to clean up all of the messes we’re leaving behind.

More to come.

This is just a draft, but I needed to get it out. Feel free to talk to me about it.

Some reflections on the joys (and despair) of conferences


It’s really easy for events to bring people of color on stage to talk about topics of relevance. What has more power is bringing these talented folks into our organizations, onto our boards and working within our walls day by day. By enabling people to change our processes, disrupt our comfort with business as usual, it gives the places we work — and the people we collaborate — more direct applications of the ways we’ve changed how we do our business.

Just inviting someone to your conference isn’t a start. When people ask how to get into the business anywhere at the intersection of UX, content or design, I often tell them it’s about forging your own path because the blueprint isn’t the same.

You should be broadening the places you conferences attract speakers, by paying people and not assuming that everyone can afford to travel to a conference and speak for a belated travel stipend. I’ve run events and know how expensive they can be and how impossible it can be to get sponsors to pony up for events unless they deem it to be in their direct interest. (Or perhaps, you know the right people…)

Amplifying the same voices over and over again doesn’t serve in the interest of anyone.

Bestowing credibility

The thing conferences can do for people who are marginalized, at least in my experience, is lend an air of credibility to people who are often otherwise overlooked. I generally don’t attend conferences anymore as an attendee unless I’m speaking. Friends already know this, but I’ve never admitted it publicly.

I hate speaker badges and dislike events that make people who aren’t part of the “in-crowd” feel isolated, but it’s hard even in the most accepting communities to manufacture an environment of inclusivity, because you’re dealing with people and it’s already hard enough to handle the other logistics of managing a successful event. At some point, you need to hope that you’ve curated enough of a community that people who are new won’t feel new for long and are able to engage and interact.

My experience is that people are tribal. They tend to hang with their coworkers if they brought them and after the first year at an event, they have their conference friends that remind me of summer camp pals and it’s difficult to break into that. Even as a seasoned speaker, I tend to seek out the new people at events. Partially because they tend to be younger and closer to my age, so we have similar things to talk about. The other reason is conferences even at the best are horrendously isolating.

Being a speaker protects me from some of that, but it’s not foolproof.

The way forward

I’ve written about this topic before and I don’t like talking about it, because I know this country’s history well enough to know that we need more than chatter to move the needle. I’m somewhat cynical about people’s commitment to progress, because the path to progress would be difficult even if the societal barriers that exist weren’t there.

Content strategy as a discipline is fuzzy. A lot of the people who do it have worked in industry long enough that they’re able to be independent or have jobs at forward-moving companies located in places that are closed off to a lot of ordinary folks. Now we have generations of people graduating university now or going back for second degrees, who might not realize such a job exists. That’s problematic, but it’s fixable through companies reaching out and by building some kind of community apparatus that engages people while they’re still in school.

We have to meet people where they are. There are no “one size fits all” solutions to intractable problems that in many cases we’ve inherited but did not create. It doesn’t absolve us of the need to fix them and it truly takes a unified effort, even if the aims and tasks are diverse.

Maybe this means some kind of non-conference related organization that can focus on these tasks all of the time. Perhaps some kind of broader community organ that invests (that means money, folks) in providing access through relationships, community engagement and that leads to roles and eventually credibility.

For all of the talk about inclusiveness, what a lot of people really need is the social capital to exist equally in a space where they’ll be taken seriously for their work, not for whatever “value” you perceive their experiences bring to the company/organization. Sometimes, it’s simply about creating the conditions to enable attendees to see marginalized people as professionals in their own right.

The Value of Conferences

Pixel Up

Was listening to this episode of the Working File podcast on the value (or not) of conferences. Specifically, the part where they were talking about reaching that point where speakers often do not attend events, but will speak at them. I have fallen into this loop where I just don’t have the time to also attend conferences that I don’t speak at.

I’m not sure when this switch happened. It probably has something to do with the fact that I went from speaking at conferences I’d attend anyway, to eventually pivoting from a “scene” to “different scenes” and eventually realizing that while there are events I’d love to participate in, there’s only so much time you can devote to such shenanigans. For me, the real truth is there’s a lot of anxiety with attending new events especially when you don’t know a lot of people. Being a speaker sometimes affords a status that sometimes makes it easier to talk to people without having to walk up to them and see what they’re into. It’s part of why I like speaking on the first day of an event, I find if people realize I’m a speaker and after they see me talk, they’re more inclined to chat with me and it saves me the awkwardness of figuring out who the ‘friendly people’ are.

As a speaker who is also an event organizer, I have spent a lot of time trying to curate the conference that’s welcoming, inclusive and warm. It’s not an easy feat, but it’s something I feel very strongly about and feel like we were able to accomplish with #GGRGT.

There are no easy answers, but there’s probably something of a conference bubble happening right now. The same 7 people get invited to speak at everything, depending on the industry. Smaller events do a much better job of providing speakers and attendees with a better experience. There’s impossibly difficult to cultivate new voices, because everybody wants to see people who have been vetted, but you can’t vet people without giving them a chance to flail (and possibly fail) on stage. I know there are events who do intensive pre-conference training that turn the speaking event into an almost full-time job, but that’s not tenable for most people.

It’s an issue that I think everyone is complicit in. Speakers, sponsors and organizers alike. More conferences need to be one-off events rather than sustaining communities that overlap. I like participating in conferences beyond just speaking, especially once my talk is done because it makes it easier to be involved. There’s a solidarity that often develops among conference speakers that add to the desire of participating to see your (often new) friends speak and shine. I really enjoy hearing people’s challenges, answering their questions and having my mind bent by someone’s unique perspective reinterpreting something I’d said with clarity I hadn’t considered myself.

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.


March 18, 2017 edition of my newsletter

Here’s the latest edition of things worth reading. You can subscribe at Tinyletter. No podcast edition this week.

Monopoly replaces boot, thimble and wheelbarrow with a T-Rex, penguin and a rubber ducky (Telegraph)
So rarely do I play Monopoly anymore that I had no idea they were retiring pieces in favor of new ones, but alas. Are you outraged? Or is this a sign of progress? Ha.

The Problem With Interactive Graphics (FastCo)
Turns out, nobody actually looks at interactive graphics? Shocked? Not in a world where millennials confess to only reading headlines and people have less time to engage with things.

The decline of first-generation college athletes (ESPN/The Undefeated)
One of the great myths of college athletes not being paid is how it’s providing opportunities to kids who’d otherwise not be able to go to college. That might be true, but it’s a lot less true now — across all sports — than it used to be, as fewer first-gen kids are getting scholarships.

The Roots of Cowboy Music: The Search for the Black Self in The American West (MTV News)
I thought this was just a good piece of writing about self-discovery, so I shared it.

The disturbing trend of homeless community college students (Washington Post)

Craigslist Is Old, Janky and Unbeatable (Backchannel)
In 2003 when I was interned at the Boston Globe, Craigslist was responsible for me finding my apartment, my computer and pretty much all of my non-work friends.

What I’m Reading: Memoirs of a Polar Bear (Yoko Tawada)
Why We Can’t Look Away From Our Screens – A review of Adam Alter’s book “Irresistible” which is also what I’m reading this week.

What I’m Listening To: Quilt – Plaza (LP)

On being known for a particular craft


How do you get to a place where people recognize you for a particular thing or discipline? Doing it a lot or doing it successfully. Perhaps the two go together?

I’m always fascinated when I meet people in real life and find out what they know. It’s the distinctive things that stick out. Maybe they’ll watch a video of one of my talks at a conference somewhere. Mostly people don’t ever meet at a conference at all, so it’s harder to translate what I do on the road with folks I meet in everyday life because it just seems so distant to them.

For these folks, they’ll remember invented Tennis Polo years ago, the shoe brand I started once or more recently, that I launched a conference or my obsession with Finnish Baseball.

As I think about ‘branding’ myself or plot my course professionally, I am always struck by what things to accentuate and what thing to put down into the background. What people remember and what I tend to accentuate don’t often match, making me think there needs to be a repositioning. That said, most of the fun stuff I do isn’t especially lucrative. I have a lot of tangible skills that I think I’d do well to share. It’s just a question of choosing what things matter and then moving the ball forward.

The real issue here is being known as a jack-of-all-trades in a world that rewards specialization.  I try to specialize, but it becomes very difficult to slough off the other skills I’ve honed over the years. So. I’ve come to the conclusion that I need to stop trying to fit myself into a paradigm that’s perhaps better suited for people with more conventional, linear professional paths. That means (somehow) melding the memorable with the marketable. It also means consolidating my myriad web presence into something a bit less confusing, so a new person discovering me for the first time doesn’t have to chase down what it is I’m actually good at.

Things Worth Reading (4 March 2017)


Here’s some things worth reading this week:

Are the 2010s like the 1930s? (The Guardian)
I’m intrigued reading about the Depression, because most first-world living people don’t have a real concept for a world with that kind of scarcity.

The world’s worst flavor was designed in a lab by accident (Tedium)
Apparently Bitrex is everywhere and we don’t even realize it.

Earth In A Suitcase (538)
What would space colonists need to take with them on a trip away from Earth?

Sex, Husbandry and the Infinite Scroll (Design Week Portland)
A piece about real life and navigating spaces in a social media dominant world.

Why do we work so hard? (1843)
Contemplating work.

Reading: The Art of the Restaurateur (Nicholas Lander)
Listening: Quilt – Plaza (LP, 2016)
Luminous, unfiltered, haunting psych-folk that teeters among three dangerously creative mind