What It Feels Like (Right Now)

Whack-A-Mole Game

I was talking to a friend at lunch today and lamenting how I still hadn’t written anything about Charlottesville, and the general tension that many Americans are feeling right now. Part of my desire to say very little in writing, was related more to feeling like the nuance necessary wasn’t possible via Twitter or perhaps without knowing where I’m coming from.

A tweet from a friend wondering aloud why so many people felt emboldened to share their political beliefs on social media during this time, is what convinced me to speak up. For days, I’ve come close to writing posts talking about growing up in a de facto segregated school district; being born and raised city that was affected (and still is) by the divestment of cities in the 1960s and 70s.

Part of my voracious appetite for American Studies relies on a need to contextualize how things got to this point. For me, the journey began with simple questions about migration, and trying to understand stories that didn’t get explained in depth during my school years.

The best way I can think to explain how I feel is something like this. America has always felt to me, much like a game of Whack-A-Mole. You just can’t be sure who is going to see you as an actual person, versus some kind of caricature, idea or something else entirely. The exhaustion of having to consistently justify your right to exist in certain spaces surely adds to the complexities of whatever thing I’m attempting.

Even with those constraints, I’ve (mostly) not allowed myself to be impeded by whatever barriers other people impose. I can deal with the present and future, knowing that incremental progress happens and perhaps, future generations will deal with these issues less than I’ve had to, much like I deal with totally different challenges than my forebears. Nonetheless, had I realized sooner that I needed to be more realistic about my options in the face of an industry that would not always see me as the ideal they sought, would have saved me a lot of grief.

I just wonder when will enough? At what point do we concede what’s happened in this country and accept that people deserve a fair opportunity to participate fully in our communities? I

A few weeks ago, I gave a talk in Vancouver at a design conference. One of the things I did, was admonish the attendees to go home and start asking better questions, to figure out what our ethical boundaries are and no longer spend our times creating systems that harm simply because someone else told us to do it. What does that mean? There are thousands of policies, projects and systems that get designed by regular people everyday based on faulty research, incomplete understanding of audiences, and aren’t always designed for the people forced to use them.

For every public utility company that charges people extra to pay on the phone versus on the internet, every city website that doesn’t work for ordinary people, and watching people fumble with UIs that weren’t designed for the wild, means that we’re costing people time and money. In private scenarios, not much can be done, but when we’re dealing directly with the public, there’s a responsibility for someone to ask the question — why? — and to track down a solution.

My frustrations aren’t about politics. It’s about policy. Politicians come and go, policies outlive them. I have no illusions that even successfully fixing policy will end the negativity we’ve seen from top to bottom, but it’ll enable a lot more people to get a fairer shake out of life.

The Difference

Growing up, the main difference in how people saw me versus adulthood is the presumption of potential. People who spent a lot of time around me — teachers, coaches — seemed to see things in me I didn’t always see in myself. In adulthood, this certainly has happened. But the other side of it has been a number of scenarios where people blinded by their own presumptions of potential, have simply overlooked what was staring in their face for something resembling a more comfortable form of what they knew to be talent.

Experiences matter because they shape how we interact with people different than us. It also means you have to cultivate your own circle of trust and find people who accentuate the positive things you have to offer; seek out and listen to folks who seem to understand the attributes you have to bring to the fore.

 

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.

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

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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

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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.