Category: Content Strategy

August 12th, 2015


“Right, when do I put the guitar on?”

There was no guitar. There was no part to play. There was only playback of a song – “Shine On You Crazy Diamond,” a 26-minute long, nine-part opus celebrating a lost friend.

It was Pink Floyd’s tribute to Syd Barrett – an original founder, a drug-addled star, a mind lost at sea. Barrett was instrumental in Pink Floyd’s early sound – a weird mix of space psychedelic and Cambridge jazz. But over time, the drugs took hold. He became a liability on stage, and he couldn’t quite come back from the acid haze.

This post originally appeared August 5th, 2015, as part of The Pastry Box Project.

One day they simply decided he was too far gone. They didn’t pick him up for a show. They found a replacement. They said goodbye.

And seven years later, as they sat listening to a recording of what would become part of their iconic album Wish You Were Here, Syd Barrett suddenly was. Unannounced, overweight, balding. Only Pink Floyd bassist Roger Waters recognized him.

Barrett was ready to play. He just didn’t realize the band had long passed him by.


There are industries that move slowly. The natural sciences are build on centuries of slow build, the slow and onerous crawl of evolution only allowing for so much new discovery. History doesn’t change, though our understanding of it becomes clearer. Water flows the same way and electricity rarely changes, so journeyman trades rarely have to scrap everything and learn again.

The web, however, stops for no one. In the past decade, every tool has changed. And while the concepts we champion are still as relevant as when A List Apart was still just that – a mailing list – the way we do things changes faster than we can keep up with.

This is not a sob story about how hard today’s web workers have it. We still sit in comfy chairs and clatter away at keyboards for a living; we still have the jobs our parents would have died to have, luckier than we may ever know. But we also have to understand that this is because we’re at the right moment in our lives to accept constant change.

Our web is one of shifting sands. Without the right balance, we’re bound to fall.


I wasn’t liked as a kid.

I should rephrase that, actually – I wasn’t noticed as a kid, which is all you need to know about my thirst for attention when karaoke night rolls around. I, like many of us who ended up falling into IRC and chat rooms as a kid, was simply unprepared to deal with the reality of relationships. I was afraid of being wrong.

I still am. Every word I write is an untapped grenade. I’m always waiting for one to explode in my face.

But despite this, I still love speaking. (Parts of it.) I still love going to conferences, and interacting with co-workers, and mingling and talking to smart people. I still think its amazing when someone remembers my name. Who me? Little ol’ Corey? Aw, shucks.

It’s this writing, though, that’s helped me push away from that kid that wasn’t noticed. I gain a little confidence every time. I’m cool with the public, y’all – married dad looking for acceptance, apply inside.

But not so much, you know. Because. Ugh. That shit’s still hard.

See, I thirst to be seen. But on my terms. Then I’m ready to sneak back into my shell. An introvert, I guess; a term that’s both overused and still crucially important as we peek from behind our computer screens and realize our generation forgot to take the opportunity to talk to real people.

I don’t want to be forgotten again. I want to be a part of something great, and I’m scared shitless that I won’t be. That things are moving away from me. That I somehow missed the memo that we’re all supposed to be doing that thing and holy what where are you going and why aren’t we talking about the stuff that I know about?

My fear isn’t of being noticed. This isn’t middle school. My fear now is of becoming irrelevant, like I’ve seen so many people do before me, ignorant or arrogant in the face of change. My concern isn’t that I’ll be passed over or forgotten – it’s that I’ll wake up and find out I could have done something to stay in the loop.

Fear of missing out, sure. More like a fear of losing ground.


Over the past five years, I have built a strong core of friends who, to be honest, I am afraid to talk to.

They are industry leaders. They are independent consultants. They are people who have their shit together.

And sometimes …

Well, sometimes, they don’t have their shit together. Sometimes, they have no idea what they’re doing. But they admit that.

They. Admit. That.

What kind of black magic does it take? Where does that strength come from, to not only constantly improve and feel at peace and chase after new opportunities and generally free yourself of the need to worry about being informed and accepted?

At what point does it feel like things are going to be easy? That the keynotes start rolling in and the projects become second nature? Where is my lake home, and where is my piece of mind?

Sometimes, I get the courage to ask.

Sometimes, I say it out loud. “I’m … I’m afraid I’m falling behind.”

Sometimes, I show my cards. I reveal my secrets. I use all of my cliches.

Every time, I get the same answer.

“You’re fine. None of us know what we’re doing. Things move too fast to ever get comfortable.”

And I feel better. For a little bit.


I don’t know if it comes from my childhood – those days when all I wanted to do was be a part of the pack, settling instead for an eight-bit broad sword and a bowl of macaroni and cheese at home.

I don’t know if it’s imposter syndrome – as overused a term as “introvert” but just as damning for a person’s self esteem.

I don’t know if I’m just lazy. Or if I’m looking in the wrong direction. Or if the constant need to be sure I’m doing things right – an over-reliance on methodology, the inability to decipher good advice from bad – is making me doubt my common sense and intuition.

Maybe, it’s just that we all suffer from some kind of doubt, and for some that doubt makes us work harder, and for others that doubt makes us look at things we never thought we’d consider.

There’s nothing wrong with being behind on something, as long as we can admit the gap and work to close it. It’s the basic structure around learning – we work to bridge the spaces in our knowledge, bringing things closer and building a stronger infrastructure.

There’s nothing wrong with falling behind. There’s not even really anything wrong with not noticing for a while. The fault lies in knowing exactly what’s wrong, and moving on as usual.

And that’s what I fear. That someday I’ll just give up. That I’ll wake up one morning and find out I no longer have a place. That I’ve unknowingly been passed by – that I was learning the wrong things, going in the wrong direction, betting on the wrong horse. And I won’t care.

I’ll be standing in a room, my old friends staring at me, wondering where I’ve been. No guitar in hand. Hoping to play the next solo.

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October 21st, 2014

The first time I spoke in front of a crowd was on what was then the largest stage in the content strategy industry: Confab, in Minneapolis.

It was 2012. I was about to drop Fugazi references and pictures of my great grandmother’s cookbook and surprisingly no fart jokes. I was hoping not to shit myself, to be honest. I had somehow attracted a standing-room only crowd, despite no one knowing who the hell I actually was.

I swallowed. And the first thing I said was a complaint.

“I just realized I missed cupcakes.”

Snack time had just occurred. There were cupcakes. Fun fact: I don’t really care about cupcakes. I think they’re fine, and I will eat them when I am offered, but there’s no way I cared more about cupcakes at that moment than, say, the integrity of Keynote or the status of my zipper or whether or not I might actually throw up right there in the middle of that conference room carpet.

But I talked about cupcakes. That’s what I did.

I started my talk. I nailed a few jokes. I started capturing the audience. I thought, “this is going well.”

And then, Jared Spool brought me a cupcake.

And I thought, “Well.”

“I guess this talk is going to go okay.”

And it did. I killed. I may have peaked early in life, presenting my best right from the get go. I may have notched a little mark in Confab history by being the annual “Where Did That Speaker Come From?” of the 2012 conference. I may have realized I did okay once I had stopped shivering in my hotel room from the “speaking shakes.”

I don’t remember any of that. I remember, instead, two things.

1. Dan Eizans audibly laughing as the only person who got the Fugazi joke.

2. Jared Spool bringing me a cupcake.

To risk sounding macabre, it’s all been downhill from there, folks.

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February 28th, 2013

Before last year, the first and only time I ever felt comfortable in front of a crowd was at my grandfather’s memorial service.

Barely lucid in his final days, I watched him slowly lose track of the corporeal and succumb to lung cancer. He was my first hero, and here he was, human, weak, no longer able to teach me about building character and Charles Bronson films. I did my best impression of an emotionally secure human and stood in front of my family and his friends and, out of nowhere, eulogized a man who helped shape my life.

And then, I gave up. Speaking wasn’t my gig. I’d just be a writer and write in the security of my introversion.

Enter The Internet

Except, that’s not what happened. Instead, I became a part of the internet, where the playing field is leveled out if you’re willing to overcome your own insecurities.

So last year, I made a change. I decided that my introversion was a crutch. I used it to stay quiet. To be safe. To keep from failing.

I pitched for speaking gigs. And then I got one. I spent what felt like months on my slide deck. I practiced once a day for two weeks leading up, and twice a day in the few days before I’d go live. I tweaked. I ferreted out the details and made them right. I picked out a shirt ahead of time and kept it hidden and clean. I gave a damn about everything.

I had never been more frightened of a crowd in my whole life.

I went through with that speaking gig, and I didn’t shit myself or ball up on the floor, crying for mercy. Instead, I stood tall. I understood the situation. I realized I couldn’t do anything about the butterflies or the room size – all I could do is be who I was and stop giving a fuck if I failed.

Karen McGrane took this entire process and summarized it perfectly in her column for A List Apart, “Give a crap. Don’t give a fuck.”. There are two competing forces when we jump into public speaking: the need for everything to be perfect, and the understanding that we can’t always be perfect. But it’s that definition of “perfect” that holds us back. Are we being perfect for appearances? Or are we being perfect because that’s what is perfect for us?

McGrane says:

“Care deeply about your personal values and live them fully in this world. Don’t get caught up in worrying about other people’s checklists to tell you what good work means to you.”

In other words, there’s a need to focus on every detail, but there’s an even greater need to focus on the details that make better things. Your shirt might not be ironed correctly, but at least your heart is on your sleeve.

My Three Rules

Over the month between preparing for my first talk to the week after, a decade of fear faded to calmness. I attribute this to three things – the three things that are most important to public speaking, and the three things Karen expertly laid out in her article.

  1. I learned to prepare. This was taught to me by Deane Barker – if you haven’t practiced your talk at least ten times, you’re already behind. The power of this preparation not only helps you for the current talk, but it also prepares you for future talks.
  2. I cared about my audience. I’ve sat through boring speakers. I didn’t want my audience to be bored. I hated that someone might call me out on being too dull. So I fought to stay interesting, relevant and, most of all, connected to the situation.
  3. I knew enough to open myself up. I’m not perfect. I’ve made mistakes, and I’ve learned from those mistakes. So instead of focusing on other companies and the ways they’ve screwed up, I talked about my own screw ups. I talked about how I learned things. I didn’t care about how it made me look, because I knew it made me look genuine.

McGrane says,

“What elevates someone’s work from ‘technically excellent’ to ‘truly great’ is the extent to which you feel like you’re seeing them live their truth, be fully themselves.”

This takes more than just a bunch of preparation. It takes a lowering of defenses, in which we stop worrying about our mistakes and start learning – no – teaching from them. It takes understanding that there’s a fine line between giving a crap and not giving a fuck, and that finding the balance between the two can open ourselves up to the rarest of combinations: being both impressive and believable in our convictions.

October 29th, 2012

I feel like I’ve been gone for a month. Here are some lists.

Airports I Visited or Landed In During This Trip

  • Sioux Falls Regional Airport (FSD)
  • Minneapolis-Saint Paul International Airport (MSP)
  • Washington Dulles International Airport (IAD)
  • Léopold Sédar Senghor International Airport (DKR)
  • OR Tambo International Airport (JNB)
  • Cape Town International Airport (CPT)

Films Watched On My Washington DC/Johannesburg Flights (In Order Of Enjoyability)

  • Brave
  • Moonrise Kingdom
  • Gosford Park
  • Quantum of Solace
  • Rock of Ages
  • Batman Begins (unfinished)
  • Men In Black 3
  • We Bought A Zoo (unfinished)
  • The Amazing Spider-man (unfinished)
  • American Wedding

Things I Did While In Stellenbosch, South Africa

Total Hours Travelled By Day (Central Time)

  • October 22, 2012 – 13:56 (9:56 by air, 4:00 by car)
  • October 23, 2012 – 12:10 (11:45 by air, 0:25 by car)
  • October 24, 2012 – 0:45 by bike
  • October 27, 2012 – 14:35 (14:10 by air, 0:25 by car)
  • October 28, 2012 – 12:11 (7:11 by air, 4:00 by car)

Animals I Touched

  • Cheetah

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February 27th, 2012

Hitting “publish” is the modern version of seeing an article hit the newsstands, or the advertiser’s tradition of the “big reveal,” where anticipation is built up and then BLAMMO there it is read it or save it for later but please oh god please just LOVE IT. Just accept it.

We publish because we want to be seen. And there’s a fear in that. For isntance, my routine is pretty standard: I write a blog post or an article, I hit “publish,” and I run for cover. I release my thoughts and, within seconds, wonder what I’ve left out of place. We all do this, I suspect. If you’re a writer and you don’t have these moments of doom, I don’t trust you. You’re obviously a robot.

We’re afraid we might be wrong – that we’ve forgotten something, or that we’ve completely missed the point. Writing is fear, and that’s what fuels the rush of hitting “publish”.

But, what if?

What if that dread was gone, if we wrote like we build, one step at a time, publishing our final drafts and then adapting those final drafts as new . What if the “final draft” was no longer a THING, and we only worked with “deployment.” What if the fear of getting things wrong was diluted by the understanding that, yes, we can change this thing we just wrote and, yes, that is completely okay with the world?

Mandy Brown writes in her most recent Contents follow-up, “Deploy”:

“How many times have you written something, published it, and then realized in retrospect that what you thought you said was not in fact what came through? (Even if you’ve never done this yourself, you’ve certainly witnessed it in others.) What if you could revise a work after publishing it, and release it again, making clear the relationship between the first version and the new one. What if you could publish iteratively, bit by bit, at each step gathering feedback from your readers and refining the text. Would our writing be better?”

This is the second time this week I’ve read about our insistance in a final draft – in the great reveal – and how it’s being overtaken by the idea of gradual deployment. I first caught it in Robin Sloan’s 2009 essay from The New Liberal Arts, “Iteration,” which says,

“Making things is a circle. You start the arc with an idea about the world: an observation or hunch. Then you sprint around the track, getting to a prototype — a breadboard, a rough draft, a run-through—as fast as you can. Your goal isn’t to finish the thing. It’s to expose it, no matter how rough or ragged, to the real world. You do that, and you learn: Which of your ideas were right? Which were wrong? What surprised you? What did other people think? Then you plow those findings back into an improved prototype. Around the circle again. Run!”

I write for two reasons these days: I write for myself as some sort of leisure, where I explore the things that are interesting to me, and I write for my job, where I help others develop the processes they’ll need to be successful on the web.

When I write for myself, I slam it out and post it. There is one iteration: the final one.

When I write for my job, I employ a process. There is no end. There is only “what’s next.” When I hand the project off to the client, my work doesn’t end – it’s designed to keep moving forward, even after I’ve stopped actually writing words and speaking to the client.

There are iterations, and the client is expected to keep the documents and theories alive.

I still write for a finished product, because that’s what I was taught. But the technology I have access to allows me to move toward something less concrete – and, ultimately, more in line with language itself: shifting, adapting and changing, all while keeping honest the history of the words.

There’s draft and there’s published. We should fight to be somewhere in between. The question is if the method to reaching that hazy middle-ground forces us to abandon the biggest thrill of publication: the rush of the big reveal.

Or maybe that’s just it; maybe, just maybe, the big reveal is already dead.

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January 13th, 2012

My daughter is four years old. The other day, as I was leaving the house, she asked me why I needed to go to work. “Why can’t you stay home?” she said.

My simple answer was, “Dear, you see, I need to go to work so I can make money, so we can have nice things and eat nice meals.” She accepted that answer as truth.

What I didn’t say was that I enjoy going to work. That there are days when going to work is a break from the kids, as much as I love them, and that while I would certainly rather spend the day with her and her brother, there are times when I need to get out and think at an adult level.

I didn’t mention that I don’t work for the money, but for the challenge – for the drive, for the thrill of making things, for the rush that comes with collaborating with other people.

I just said I was going to make money. It was the easy answer. Because I didn’t have the time – nor did she have the attention – for me to tell her truth: that it’s much much more complicated than that.


If there’s one thing that fuels today’s grab for pageviews, it’s opinions. Hard ones. This or that. Nothing in between. Nothing that veers into the hazy grey field of compromise.

“Summarize that,” they say. “Give me the bullet point version,” they demand. Time is of essence. Boil it down so it no longer needs thought.

So when we talk about whether the New York Times should be more vigilant in their fact checking, or whether yoga will cause you irreparable harm, we’re predisposed to boil it down to the most simple argument. I know I do this. We all do, in some ways.

Maybe it’s not our fault. Maybe we’ve been taught to believe that the ability to create concise descriptions of complicated things is a sign of success when. Really, it’s the opposite. You’ve succeeded when you can explain a complex subject without losing the nuance. I know: that’s hard to do. So we summarize. So we cut corners. We ignore the complexity.

It’s not a matter of missing the forest for the trees – it’s that we’re cutting down all of the trees and wondering where the forest went.

On Argument

A year and a half ago, during the 2010 South Dakota Festival of Books, I watched Michael Hart – the late founder of Project Gutenberg – and Michael Dirda – Pulitzer Prize-winning book critic – present a panel on “Reading in the Digital Age.”

As one might expect, Hart spoke at length about how the printed book was dead, that all writing should be done digitally for the benefit of mass consumption and for those who may not be able to afford a printed tome. Dirda, on the other hand, spoke about the necessity of aesthetics, of the tactile nature of holding a book in your hand, of the feeling of being that you cannot recreate in an e-reader.

Both made some good points. But the title of the panel is misleading. This presentation was no more about reading in the digital age than it was about koala mating habits. Where we expected some sort of solid discourse on where print vs. digital may eventually compromise, we instead received a kind of ribald sniping. It was a battle between two opposing viewpoints, both refusing to admit middle ground, incapable of giving an inch.

While the answer lie somewhere in the middle of the pitch, these two men fought over which side of the field to enter.

Respecting Complexity

If a single idea has followed me around this year, from politics to art and work to friendships, it’s been this one: “it’s more complicated than that.”

It’s centrally important to seek simplicity, and especially to avoid making things hard to use or understand. But if we want to make things that are usefully simple without being truncated or simplistic, we have to recognize and respect complexity — both in the design problems we address, and in the way we do our work.

Erin Kissane, “What I Learned About the Web in 2011” via A List Apart

My experience at the South Dakota Festival of Books is no different than any experience one might find watching cable television, or at a political debate, or when discussing which Led Zeppelin album is the best. We’ve been trained to take a side and dig in for battle.

When we go to battle intellectually, we find comfort in absolutes. They afford us a bit of security. There are no holes to be poked in our theories.

Part of the challenge of art and science and rhetoric is in finding the nuances; there is no topic worth discussing that doesn’t hold some grey area, and there is no grey area that is worth ignoring. But grey areas? They’re hard. So we ignore them. And that’s how misinterpretation seeps into our lives.

Naming Things

Take, for example, the industry in which I work: web design, development and strategy. For the past several years, people have tried to put together a simple, concise description of content strategy – what is it, and how do we quickly explain it to our bosses? We understand that there’s a need for that description in a business sense, but our answer is often lacking in nuance. We trade length for clarity; we discard the messy details to gain a certain level of buzzworthiness.

Truth is, content strategy means different things to different people. What’s more, THAT’S OKAY. Just as “web development” means different things to different people, we still have freedom to interpret our work in a way that makes sense to us.

So we stick with “content strategy” – an awkward word that barely captures the extent of what we do. But we’re not alone in this: language is hard, and though we struggle to assign simple words to complex arrangements, and though they may seem trite and inaccurate, oftentimes it’s the best we can do.

Communication isn’t perfect. Again: THAT’S OKAY.

This is not an industry-specific thing, either. Ask someone to explain the scientific method. Depending on their field of expertise, you may hear several variations of the base process. Ask someone to explain something with a clear purpose and structured set of rules – baseball, for instance. Ask a baseball fan. Ask a baseball historian. Ask someone with no connection to the game. To some, it’s a game. To others, it’s a past-time. To the haters, it’s a distraction.

Black. White.

Words allow us to communicate. But they also fail us, in that we’re driven to compress theories that should, in fact, become more robust. We’re taught to say more with less, to edit and edit until there’s nothing left to chance, to push things into a smaller box. So we cut the non-crucial elements. And we lose the nuance. And we wonder why this seemingly complicated theory has been boiled down to a Cliff’s Notes version – all solution, no reasoning.

Sure, most things should be said in fewer words. But there are a lot of things that should be said in more.

We’re challenged to understand the future in as complete a way as possible. To shy away from absolutes, and to embrace the grey area, charging in full speed and making sense of the fray. There are discoveries there. There is truth. There is completeness.

We can’t take one side or the other – not in good faith – without understanding that, regardless of the subject, it’s often more complicated than that.

War is good. War is bad. It’s more complicated than that.

We should be liberal. We should be conservative. It’s more complicated than that.

We should fight to stay neutral, and we should always look at all angles of a subject, and we should stop trying to sum up incredibly complex processes and concepts and feelings into simple, single-serving soundbites. We should run to the middle and be implicit in our embrace.

Except, let’s be honest.

It’s more complicated than that.

December 7th, 2011

If you’re into nerdy things like work methodologies and the nature of the content industry, you’d TOTALLY be into the article I wrote for Contents Magazine, a publication about all things content.

From “A Content Methodology Primer”:

It’s romantic to think that content work is an art, all brandy, pipes, and wood grain. But it’s not. It’s a process. A messy, sticky, multi-disciplinary process that begs for structure, consistency, and guidance.

That’s a daunting task. Content wants to be messy. It wants to roll around in the mud. It wants to be gross. Our job is to pull it together—to take the guesswork out of creating and curating it—and to treat content work as something closer to a science.

And, if you’re NOT into that, you might enjoy this video of a mullet/mustache combo whistling “Georgia on My Mind.”