What will we leave behind?

If you’ve been following me lately, you know I’ve been on this renaissance of playing skeeball, a bowling-inspired game that’s been around since the early 20th century.

Reading publications from 1909, you get a sense of the way the world thought of itself. We’re not great at seeing far in front of ourselves as humans, we only see what’s in our view. Maybe this is the reason we’re so bad at long-term planning and why future generations are consigned to look back on the past and ask, “what were they thinking when they did this?”

At design & content conference two weeks ago in Vancouver, I challenged the audience to ask themselves what the future would look like for each of us. Not just in our everyday lives, but through the work that we do each day to encourage, enliven and empower others through mission-driven work that doesn’t just pay lip service to the ideals and tenets of positivity, but through demonstrating real, actionable change.

After my talk, someone asked me “what am I supposed to do? I think about this stuff sometimes and I get overwhelmed.” I replied, “when you go home, find some organization that might be able to use your help, tell them what you can do and ask if there’s something they need.” 

By bringing these ideas to light, I’m not implying that I’m somehow above the problem. I’m right here in the muck with everyone else. I’m only trying to highlight what I’m seeing as I move about the world, because it’s clear that not enough people are saying the things that many of us are thinking.

What to do next

I’ve been contemplating my own direction lately. I am very interested in the work at the intersection of where design, policy & code meet. It’s clear in a variety of ways that not enough people understand the underpinnings of what goes into designing the tools of the future. Not enough people are thinking about broader communities and how all people are impacted when we design for the ideal few.

I’ve been thinking about the design of things for a while. But not just the form factor, the actual ways that we build systems. Reading the history and how dark patterns are part of our everyday structures means that we’re all complicit. How do we solve for this? We have to arm ourselves with the knowledge that things are wrong, they’re screwed up and that by not embedding that into the ways that we make things better means we fail.
Working on products is interesting, but focusing on the facets that go overlooked sounds more compelling. What would it look like for designers to work in underserved communities tackling large-scale challenges? Right now, we apply a lens that’s largely focused on business, economics, and growth-oriented thinking. These assumptions apply faulty logic, often ignore history and don’t consider the structural challenges that impede progress at all levels.
Stop burying the lede
For all of the mentoring I do, I’m not so great at communicating my experience. I can do it one-on-one, but because so many people have different things they find “impressive”, I find myself often having to recalibrate my message in dramatic ways to fit whatever needle I’m threading through.
Often, I’ve thought this issue is a consequence of living in a small Midwestern city rather than somewhere much larger where my relationships I’ve cultivated through speaking and the internet writ large would perhaps come into play. I realize you can’t do it all by yourself and I’m at the point where I’m kind of doing everything the hard way.
I’m retrofitting my bios and other websites over the coming weeks to do a better job of communicating my value, what my interests are, and what type of work I’d like to be doing. For instance, I know I don’t want to be a professional speaker. It’s cool if that’s your thing, but for me, I just find speaking incredibly draining. I speak at 5-7 events a year and that’s more than enough.
I enjoy hands on work. I care about the process and distilling big ideas to people whether they have a broad technical knowledge or (more likely) not. Government moves a bit too slowly for me long-term, so it’s clear I need to be in a space where innovation, creativity, and imagination are valued rather than stifled or buried.
This is really the start of a semi-public conversation about my own direction. I feel like a lot of people do a good job of telling you where they are, but not how they got there.
Maybe this will prove useful to someone.

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.

Show Your Work

You probably have a job like I did. Maybe you’re even an intern. Whatever. Anyway, you have some job and you’re doing whatever they’re asking of you. Some days, that’s writing some stuff. Other days, maybe it’s design and code. Regardless, you’re always doing something.

Here’s the problem. When you work at the intersection of tech and you’re doing work that nobody else around you understands, it becomes necessary to develop a shorthand for communicating with laymen.

At the risk of burying the lede, you need to start showing your work. Document what you’re doing, because nobody will ever tell you to do it at work. It’s easy to get really good at your job by simply knowing what you know, melding your processes with whatever your organization requires. It’s tempting when you’re a lone ranger to eschew with formal processes, because “people aren’t going to it anyway.”

The reason is easy. It’s the reason people laugh watching The IT Crowd or the stereotype of the cranky, know-it-all tech person exists. Having started my career as an IT guy, I knew the trope well. When I switched to the web, I was adamant about making the work accessible to people. Frankly, this applies whether your job is making artisanal french fries or doing UX. Most jobs have a language, but unlike working on your car or the plumbing getting stuck, there’s not a real need to engage in the language of the web everyday. It’s not until something breaks or needs to be fixed, that you need to start understanding what your “web person” is talking about.

Most of the people reading this on Medium somewhere probably don’t identify with this. If you’ve got some great job at some bleeding-edge startup in some semi-hip city off the continental shelf, you’re not dealing with the things ordinary people do everyday. The ones who are too busy to tweet; with bosses skeptical of social media and wondering why everything on the web takes so long to actually make.

Everyone has some kind of process. Documenting what you’re doing, even if it’s just for you, is a good way to signpost throughout your process. If you’re about to embark on an effort you’ve never performed before — a web redesign, user research, content audit — take the time to do some research about what other people have done before you get started. Do a search for other people’s frameworks, adapt them and move on. It’s tempting when you’re a lone wolf in an organization to feel like you need to know everything. There’s no one around to tell you otherwise. In fact, it probably feels like people actually do expect you to know everything because in their minds “that’s what we hired you for.”

Part of being a subject matter expert is understanding how to learn. Having a documented process, more than anything, gives you a chance to look back years later at what you did and helps you improve your methods. It took me years to realize how critical it was to document mental models and other tools that I used consistently on projects both large and small throughout my career thus far. I have some tools I used a lot, but the process of actually keeping track of my own progress came fairly late for me.

You can start today.

Finding your inner superhero

Hit Girl from Kick Ass

Seems like these days, a lot of people are looking for mentors to help them navigate the waters of professional life. Who can blame them? It’s a scary world out there and it seems that for every person you know who makes it, a dozen more step out on faith and despite the Facebook & Instagram feed that says all is well, a more intensive glimpse at their lives would say others. Even if they’re doing great, we can all too often benchmark ourselves against what others are after in their own lives. This negates our own desires, goals and things that are motivating us towards whatever we really want to be doing.

If I had a dollar for every time I thought, “If I knew then what I know….,” I’d have a lot of dollars. The thing is, I’m less interested in going backwards as I am trying to move forward employing what I’ve learned to help me make better decisions now and in the future. So long as I do that, I don’t think past failures are all that bad. My dad always says — and I agree — it’s about making different mistakes not about making the same ones over and over again.

With that being said, I’ve been reflecting a lot about work lately. Talking to friends the past few years and hearing their own challenges, it’s pretty clear to me that lots of us are wrestling with many of the same insecurities, worries and wonders.

The thing I’ve learned more than anything, is nobody is going to save you. All of the advice in the world doesn’t make it any easier to act, if you’re not sure where you’d really like to be. I re-read most of “Escape From Cubicle Nation” this week. I read it a few years ago, but I wasn’t as ready for it. Because as I read it this time, I felt like it was written for me. All I did is shake my head vigorous as I got through the first few chapters. Reflecting on it a few days later, I’ve realized that my struggle is feeling that the uniqueness of my circumstances weren’t like anybody else’s.

I couldn’t shake the feeling that my mistakes were worse than everyone else’s and all of that somehow made me unfit for the future I wanted for myself.

I’ve been canvassing a lot of my friends and professional colleagues lately to bounce off of them how they ended up where they did. So much of our destiny is about the confluence of events that lead us to where we are at a certain point. More than that, it’s about choices. I think sometimes it’s easy to romanticize the amount that fate plays into our decision-making process, but when I think about everything that’s led me to this point right now, it’s really about a series of choices. Some of those choices happened twenty years ago, but nonetheless, there were choices.

When I set out to write this post, my goal was to come away resolved with a pact to write everyday for the next few days. Every time I read people who are involved in writing for a living, they talk about the commitment to the process. That no one is too good for practice and that sort of thing. All of this is instructive, except my job isn’t to write. It’s not even my passion, it’s just one of the most effective ways for me to reach out to you strangers and friends among you.

I’m less interested in doing things for the sake of doing them in 2015. It’s really about embracing a mantra of consciousness action. I want to do things that matter, while realizing that not everything I do will matter to anyone else. And I want that to be okay.

In a world full of ninjas, rockstars and gurus, I just want to discover my own inner superhero. I know he’s in there, because half of what’s propelled me here is driven by a spirit that’s far bigger than anything I can contain. The problem is, superheroes hide. We don’t see them all of the time, because if we did, they’d be the kind of fallible heroes that we don’t acclaim until they’re lost forever.

My goal in the coming days is to use this space and others given to me, for exploration of a different sort. I think we have a lot of power within ourselves to affect change in small ways and in big ways every single day. For too long, I’ve personally succumbed to the whims of whatever was around me for a fear of being perceived as something I’m not. In the process, I’ve masked my superhero and kept him out of situations where he could truly help.

The funny thing about superheroes is they’re usually normal people. I call them Clark Kent Tendencies. They bumble and are usually the last people you’d expect to save the day in their normal work clothes. It’s not until they put on the mask and go to work, that people become believers. Except, we don’t know who they are in real life and that’s part of the mystery. I have a lot of those Clark Kent Tendencies, but when I’m giving a talk or interacting with other smart people, I almost have an out of body experience because I don’t always recognize myself.

“Who is that guy? Wait, maybe I do know what I’m talking about!”

I remember thinking at a certain point last year, that I didn’t want to live the rest of my 30s doing things I didn’t really want to do or living places I didn’t want to live. I’m really cognizant of how important each day is and this is just my opening salvo towards living, working and doing better.

It starts by rediscovering my inner superhero.

3 things I’ve learned about meetings

Whiteboard with markers

Meetings for a web person can be difficult because often times you’re in a room full of people who have no idea:
1) What you do.
2) How long it takes to do what you do.
3) Need something from you.
4) Want it faster than is often plausible.
5) Will often implore you to cut corners to deliver what they want.
6) But want it with the same quality that would take as long as it normally should.

I’m all about delivering to the customer, but even Amazon doesn’t offer “instant” shipping. There is a process. There are sometimes delays in every supplychain. But when we deal with human capital, we often ignore these details and step our foot on the gas harder in an effort to make them go faster. And it works, because people want to do a good job & don’t want to lose their jobs.

Let’s talk about meetings.

I’ve heard a lot “meetings are how we get things done,” a phrase that makes me cringe. It presupposes that the only way to do work is to get a bunch of people into a room and have them make decisions. This would be fine and ideal if that’s what happened. But in a place with a “culture of meetings,” isn’t as interested in decision-making, but rather than spending a lot of time talking in circles. When there is no cost to people’s time, you can simply schedule a meeting without regard for whether a meeting is actually necessary or not.

Early in my career, I had a boss who was one of my favorite people to work with. I just liked being around her, listening and learning from her. Years later, I’m still waxing poetic about her methods and ways, because she had a deftness with managing people and priorities the likes I haven’t seen much since. I assumed since it was my first job in higher ed, that all supervisors were this way. I’ve come to learn the opposite is true.

Here are three things I learned about meetings over the past few years:

1) Get to the point. Some of my best meetings were simply walking and talking affairs where someone important would be heading to a meeting. “I feel like we’re on west wing when you walk and brief me as I head to other meetings,” is what my boss used to say. What these walking meetings did for me was distill the facts down to a few things that needed to be communicated quickly. She did her part by asking the right questions. Even if we had to follow up later (as we often did) the foundation was set and it was far more useful than a late night email.

2) Everyone has a role to play. Rather than only focusing on the skill participants of every job, you have to assess what everyone’s role is and prepare them for that. Huge meetings where everyone has to participate and drone through an hour or more of information where only 10 or 15 minutes might be relevant to them isn’t always the way to go.

Sports are instructive in helping you understand that everybody has a position to play. When I coached HS tennis, it was often my bottom of the roster players who would make the most progress in a year. I learned this from my own experience as a bottom of the roster player on really good teams, that you need to nurture those players because the top players often want to work and get better — as they have something to aspire to. Whereas the players at the bottom don’t always feel like they have as much to play for.

Everyone has to attend practice, but during that practice they’re not always doing the same things. There’s value in shared experience and also good leadership practice to communicate how pieces of the puzzle can be relevant to everyone within the organization. But a meeting isn’t going to drive home that message by itself.

3. Keep (the meeting) small. I’ve been running meetings since the days of high school where I learned Roberts Rules of Order. Since those days, I’ve seen throughout professional life that not much has changed since those early days of leading meetings amongst high school and college debaters. You need order, but in grown up meetings everyone often feels entitled to speak. “Peacocking” where the need to show ones feathers is prevalent is one of the biggest reasons to keep meetings small, short and topical. In the era of communication overload, there are no shortage of ways to get together. But bringing 50 people to a room to discuss something they’ve only heard about once (or never) is not the way to introduce a new idea or to get maximum impact for whatever you’re trying to roll out.

How many times do big meetings end with “we’ll meet offline about this?” Exactly. Maybe you should start there, rather than begin there?


It’s all about communication. Meetings are meant to help us do the business of our companies, but we can’t do that if all we do is sit in rooms staring at each other (or our screens) for hours, dreaming about how to prioritize our time after all the meetings are done.

There needs to be balance, a flow & respect for the people who participate if you expect your meetings to achieve anything.

Finding your flock in the working world

My understand is that when you see a flock of birds, the ones at the front don’t spend the entire trip leading. The birds take turns to conserve energy. The other thing I found most interesting about bird flocks, is that there are actually diverge leadership groups at different times trying to steer the flock elsewhere and some will indeed do that.

The funny thing is, the birds behind start to realize that the more of them that follow one, the easier the travel gets as they can draft behind the others in the flock and conserve energy. They take turns doing this and it makes the trip across long distances possible.

I think a lot about leadership and for a long time, I thought if you’re passionate, work hard and care about other people that folks would naturally see what you’re bringing to the table and want to support you towards your goals. This somewhat mistaken belief was borne out of years and years of supportive people identifying me as someone they thought should lead. I’m talking all the way back to grade school, where I’ve had teachers and peers who have mentored me, lifted me up and told me I was worth a damn when I didn’t always feel like it. For all of my penchant for leading, speaking up and sharing what I know; I’ve spent most of my life trying to recede to the back. But time and time again, people have refused to let me not shine my light.

For this I am beyond grateful.

My professional life has been marked by people who have pulled me aside or put me in leadership roles consistently. From the boss at the software store in high school who made me his 3rd in command a month after I was hired to my first boss in higher ed who decided that she had enough faith in my abilities to let me lead a redesign project & committee that was comprised of all VPs and our President and felt comfortable enough not to attend those meetings because she knew it was in good hands.

These kinds of experiences I have shaped how I’ve seen myself as I moved up the ranks, assumed more responsibility and accept greater challenges. Even when things don’t work out, I’ve come away with a much better understanding of what my role is. But more than anything, I’ve come to understand that not everyone is going to have your best interest at heart. Not everyone is meant to be a mentor, not every person who comes into contact with you is concerned about your professional growth or wants to see you succeed on mutually acceptable terms. The trick here is if you’re not fortunate like I’ve been to have great people support, encourage and bolster me and find yourself in an unsupportive professional environment is realizing that you have a responsibility to accept change and to make it work for you.

I don’t mean making the job work for you because not every situation is salvageable in that way. But if you’ve reached a point where you consider yourself a competent individual with some value to offer, then you need to figure out ways to demonstrate that. People will notice. Even if they don’t, you can’t let one situation define you. Your work, your actions and your strength of character will define you over a period of time. It might takes years and you might find yourself searching far and wide, but eventually you’ll find your flock.

But you need to get off the ground.