Dylan Wilbanks

Dylan Wilbanks is a web roustabout, raconteur, and curmudgeon currently practicing as a user experience designer in Seattle. He’s spent over 15 years designing, building, and perfecting online experiences, and every once in a while does a good job. Occasionally, he speaks at conferences like SXSW and Webvisions. He created one of the first Twitter accounts used in higher education, but that was an accident, and he's really sorry about it.

With Kyle Weems, he co-hosts Squirrel And Moose, a podcast about designing and building the web, when they remember to talk about it.

He likes nectarines.

You can read his tweets at @dylanw and learn more at dylanwilbanks.com.

Published Thoughts

So, how do I want it to end?

I’m 43 now; I’ve now been a legal “adult” far longer than not. I’m starting to see an end coming out there on the horizon, distant and fuzzy, but certainly closer than it was a decade ago.

Time is precious. Time is short.

When you’re younger, you crave attention and admiration. You want to be with people who are cool and can make you cool. But as you get older, you start noticing that some of your so-called friends are toxic. So you drop them. Things that you once felt compelled to do no longer feel worth the effort. You cut free from things not giving you value. You prune down more and more to the people you love and the things and activities that give you joy, the things and people that are worth the time and effort you put into them.

I have started making choices to invest time, in family, in friends, in people who ask me for help, for mentorship.

I put money into causes I care about that, things that I see as investments in the future. The environment. Libraries. Public health. Art. People.

I try to say “I” less and “we” more. (Clearly, that needs work.)

I don’t put myself out there as some “ally,” but as someone who, being a mostly-white male American, is going to make a lot of mistakes when it comes to non-white, non-male, non-American issues, but is going to keep trying until I get it right.

I write. These last two years have been my most prolific for writing. The comments and responses I’ve received from these months of the Pastry Box make me happy that others are taking my little words and turning them into far bigger things in themselves. They also make me regret not writing those years when I chose to work too hard instead.

But time is short. The end is coming. Like Monty Brewster, I am in a rush to spend my personal capital before time is up. Am I doing enough?

I have my own doubts about my intentions. Vain and egotistical? Perhaps. I worry that my need to invest in others comes off as pseudo-colonial, like I’m trying to fix other people, even though I shy away from offering pat answers… or even answers.

But all you can do is keep trying, failing, cutting free, learning from your mistakes, and keep pushing yourself — and others — to be the best possible version of yourself you can be. To be better than you were yesterday.

So how do you want it to end?

I ride the 41 bus to and from work in downtown Seattle. My house is about a 10 minute walk from the largest mosque in Seattle, and thus I share my neighborhood with Muslim families from Africa and Asia. So I ride in to work every day with people in every form of Muslim dress: burkha, hijab, simple headscarf, to no headcovering at all.

Sometimes, as I’m riding the bus, I think about my family, in Middle America, telling me of their fear of Al-Qaida, ISIS, the Muslim Brotherhood. In my hometown people actively protested against a Muslim veterans group marching in the Veterans Day parade. If they knew I was on a bus full of “those Jihadist Islamists,” what would they think?

Then I look around the bus, and there's one constant: All these Muslim women on their cellphones texting, reviewing Facebook and Instagram, listening to music. Just like every other person on the 41 bus.

We fear “others,” people who are not like us. And it’s not just Muslims vs Christians, it’s religionists vs atheists, Republicans vs Democrats, Apple vs Microsoft, even people who read The Nation vs people who need the latest Kardashian news.

We need “others.” We need them so that we can define ourselves as the right thinking, right acting sorts, even when our thoughts and actions aren’t exactly the best. It’s easy to “other” someone. And each of us, no matter how hard we try not to, does it. We need someone to frame our beliefs and actions against. So we “other.”


Last year I chaperoned my daughter’s class on a nature sleepover trip to a local camp here in Seattle, one oddly positioned in between a housing addition and a golf course. Her school draws from the same neighborhood as the mosque, so you see the same mix of Muslim children in the school body.

(One thing I like about her school is that it draws all races, ethnicities, and income levels. The school ran an auction that drew multi-thousand dollar bids for African safaris and primo parking spaces the weekend before it ran a food drive for students and their families that were food insecure. Seattle can be a homogenous and segregated town; it’s good to be a part of a community that refuses to buy into that.)

At one point one of the boys, a Somali fifth grader that was almost as tall as me, got separated from his nature group wandering the woods; I was asked to get him back to his group.

He didn't know much English, and I'm an introvert with new people, but we did the best we could to communicate.

As we got deep into the woods, he stopped talking and started looking around. Tall firs and pines, birds, ponds with tiny fry and water walkers. And he was wide eyed to it all. I remember explaining water walkers to him — how they move on the surface tension of the water, and it fascinated him that they could do that, walk on water.

So, here’s this boy. His family emigrated to America as refugees from a generation-old civil war. His family lives just a few blocks from my house, he’s learning English, and they’re trying to make due in this cold, rainy, ugly lovely town in this alternately welcoming and "other"ing nation.

And he’s looking at these tall trees he’s never seen before, these bugs walking on the water. All things I’ve taken for granted.

"Wow," he kept saying over and over.


These “other” people are just like us. They live, they die, they eat, they stare at their Facebook feeds on their cellphones. But we forget this. We are quick to call people wrong, call them Evil when it’s their thoughts and actions that are off.

And people are often wrong. Heaven knows how many times I’ve stared in disbelief at whatever wrongness is bubbling through my social media feeds. Bad medical advice. Simplistic political thinking. And sometimes, they’re just being assholes.

But you can call someone wrong without denying their humanity. And you can recognize strangers, others, as different without living in fear of them.

You can grant them dignity, even as they may not grant it to you. When so many wish to deny dignity to others, the most unexpected, and empathetic, thing to do is a simple acceptance that the other person is a human just like you. In the Gospel of Matthew, Jesus says, "...whatever you did for one of the least of these brothers and sisters of mine, you did for me." Our actions towards those who represent "the least of these" demonstrate how willing we are to give empathy and dignity to those we, or society, judge to be "unworthy" of it.

I cannot say it’s easy. I cannot say I’m any good at it. Sometimes the pinprick of fear comes to me on the bus. But when I see the cellphones, when I watch the awe of an elementary school kid, I remind myself that I’m just as scary to them, and it’s OK, we’re all dealing with our own personal shit, but dignity and empathy will get us through the day. And, ultimately, it will allow us to push back against the terror and fear so many profit off of with their words, actions, and bombs.

I was talking to my daughter. Her grades were very disappointing, and it’s because she’s not doing the work. So I pushed her on this, and she broke down, announcing she’s a total failure.

I knew the feeling. I’ve been afraid of failure all my life. And I chose an industry (the web) and a practice (UX) where failure is not only common, it’s an accepted part of the process.

There are many moments I want to crawl into a hole and hide when I’m working on design. They mostly involve the awkward minutes, hours, days I’m staring at a piece of paper… or a whiteboard… or my computer screen and waiting for the moment the ideas start to come out of me.

And every time, I feel embarrassed that yet again it took me three days to pull together a design plan I’m happy with. And every time, it turns out just fine, and I promptly forget the next time around to give myself the space I need to face my fears.


Five years ago, I went to Cincinnati to give a talk at HighEdWeb, the pre-eminent conference for people who work on the web in higher education.

I was incredibly nervous about what I wanted to talk about, and the anxiety had created a disjointed mess of a slide deck. I’d had a disaster of a presentation at SXSW the previous year, and it still left me shaken.

To make matters worse, plane trouble left me stranded in Salt Lake City, where I was stuck with all my fears in a dingy hotel room overnight.

Unable to sleep, I did the only thing I could do to assuage the anxiety: I rewrote the talk, piece by piece, on a hotel notepad at 4am. I ripped out slides and replaced them, fought the hotel wifi to get Creative Commons licensed photos off Flickr, and rethought the entire point of the talk. On the plane to CVG, more of the same, only with slower wifi, but I finally had a draft I could live with.

I got in for day one of the conference. Everyone was so… good at this. No, they were great. And my deck sucked by comparison.

I skipped out on some of the partying to practice the talk, twiddle a couple more slides, and in the end, write the talk out in longhand. (If you’re going to be anxious and neurotic, might as well go all the way.)

Day two and time for me to give the talk. It was 5:30am back home, I’d barely slept, and here I was with this ridiculous talk in this city I’ve never been in before and…

And that’s when the fear finally stopped. I was on stage. I’d been here before, a dozen times. I knew what to do. If I failed, it would be over in 45 minutes and I could get on with my life.

The words that came to mind were “F**k it. Let’s go.”

So I went. 45 minutes later, it was over. Only, it wasn’t. They had me reprise it the next day, twice. Then the conference attendees voted me Best Talk. (That was a hard one to explain to my skeptical coworkers who didn’t understand why I would “go to Ohio to speak at a conference when I was just the web guy.”)


And yet, the same thing happens every time I do anything creative. I spend time getting myself to “F**k it, let’s go.” Experience has taught me, to a point, that I should expect this, but it still doesn’t help when I’m in the midst of that moment of unknowing. And it doesn't assuage the feeling that I'm wasting time.

From the conversation my daughter and I had after her breakdown, I discovered we shared a dark fear: The fear that we’ll embarrass ourselves and look stupid because we don’t understand what’s going on.

Because that’s the feeling I’m really having in those minutes, hours, days before I start designing. I’m trying to understand. I’m trying to make myself not feel stupid. Getting to “F**k it, let’s go” is letting go of that fear and becoming dumb in order to understand.

So, I practice. I remind myself it’ll get easier if I do the work. And I remind my daughter of the same thing: The practice of the practice is what makes us smart, and the only truly stupid thing is living in fear.

And now she and I roll up our sleeves and do the work. She has her math homework adding and subtracting negative numbers, I have a messy project with disparate stakeholders and blurry goals. But I remind her to “F**k it, let’s go.” (Well, the PG version.) The fear isn’t worth the time we give it.

I just have to keep reminding her -- and myself -- of that.

When interviewing job candidates, I don't ask about strengths and weaknesses anymore. Instead, I ask about frontiers.

Frontiers are the places we haven't explored, but we want to (or need to). They're the places we know where need to grow and want to put the effort into doing so. And they're things we know we need to learn and we yearn to do so.

I ask for frontiers because I want to know if the interviewee feels like they have more to learn. We can rest on our laurels and coast, or feel like we've "arrived." I haven't found people who think they are a "finished product" to be great hires. I want to hire people who still hunger to learn more and want to strive to be better. When I talk about hiring for "upside," this is what I mean.

I also want to find people who are honest and transparent about where they need to grow. Do they know themselves well enough to know what they don't know? Do they also know where they shouldn't put their time and effort in growing?

Once I explain what I'm looking for (and, unfortunately, it usually takes a minute), the answers I get are very different from asking about strengths and weaknesses. They're things like "I want to understand the domain I work in more." Or "I want to learn how to do this Lean UX idea I read about." Or "I'm learning how to paint landscapes because I want to better express my design skills." By avoiding a loaded term, I can ask what gets an interviewee motivated to be better at who they are and what they do.

We need to have that hunger to explore. To learn more, to try new things, and to find new insights about how we work and how we work with others. In the best work environments, we are better at what we do every day because we want it and our employers nurture the exploration.

What are your frontiers? And how will you go about exploring them?

Shut up and listen.

Bernie Sanders, the White Progressive Hero Presidential Candidate for 2016, had his Seattle campaign rally disrupted by two African-American women protesting for Black Lives Matter. In front of a restive crowd of white Seattle liberals, they suggested the town is racist. And the lilywhite Seattle progressive crowd turned on them, shouting racial epithets, booing moments of silence for Michael Brown, and reminding everyone that just under that thin veneer of upright left-wing anti-GMO anti-corporate lay the dark, dark heart of a half-millennium of ingrained American racism.

And as someone who has been a Seattleite for two decades (this month), the whole incident hurt. Seattle does have a problem with racism, but it’s not firehoses, dogs, and firebombing. It’s the lasting effect of redlining, the inequity between majority-white and majority minority schools, and the complaining about “black men” driving through their neighborhood on the local chatboard.


A few days after the Seattle rally, the arguing over conference “codes of conduct” flared up again. And at the same time as that piece was published, Katie Kovalcin reported her trouble with a conference failing to protect the harassed.

Women, people of color, and sexual minorities complain they don’t feel safe at conferences and don’t trust conferences with their safety. They are pushing for “codes of conduct” to be standard around the industry. Male conference runners and attendees react by saying codes of conduct won’t work — often while appearing to belittle the very real concerns of a plurality of conference attendees.

But men have opinions, you see. And opinions must be expressed. The Internet is a place created to hold everyone’s hot takes, no matter how scattershot and ill-informed. But Someone Must Say Something About This. Someone Is Wrong On The Internet.

We respond like that Sanders rally crowd, wondering who the hell these people are talking about. A woman demands a safer web, and men freak out because we are safe how dare she say we are not. Someone who finds a Web community biased against people of color, and white folk freak out because but we are not racist stop saying we are racist. Someone asks for a Code of Conduct at a conference, and we freak out because it does not do anything and we’re all adults right? (And did we mention everything was fine until they showed up?)

We shut down. We don’t listen to the complaints. We don’t parse the solution to understand the problem it’s supposed to solve. We don’t think hey, maybe they’re not talking about me as the problem, but me as someone who can be the solution.


Our Weltanschauung within the web industry has stagnated. We’ve hidden from the real concerns of the world — racism, sexism, homophobia, economic inequality — partially because we promoted the Internet as this libertarian wonderland where “everyone is equal,” and partially because we’ve pretended the Internet was built and run by men, mostly white.

But now the world is on the web, and these billions of people are not mostly male, mostly white. And they are asking why women are being harassed for speaking out, why the word “f**got” is used on chatboards as a term of endearment, and why don’t we understand that our beloved “disruption” has economic and social consequences?

The Great Leveller that was supposed to be the Internet became more of a Great Mirror, reflecting back a broken, inequitable society that protects the powerful and predatory. And that Great Mirror reflects back all the heat and light of the powerful and the predatory onto the vulnerable with a painful intensity.


I’m angry. I’m angry that we’re still stuck in this world view. And I’m even angrier that the primary solutions people offer up are Get Off The Internet and Let’s Just Act Like Adults.

Get Off The Internet… well, in a time when 40% of the world's population and over 85% of the US has Internet access, when it’s well-nigh impossible to apply for a job without the Internet in almost every Western country… is this a stupid idea, or the stupidest idea ever?

Let’s Just Act Like Adults… I have been an adult for over 20 years now (in the eyes of federal, state, and local laws). What I’ve learned about adults is they’re assholes. They’re greedy, mean, vindictive, and selfish beasts who couldn’t give one squat about others unless it is in their best interest to give a squat about others. Asking humans to act like adults is meaningless unless there's agreement how an adult acts. We'd be better off telling people to act like kindergartners; at least they don't build websites to harass others.


As designers we’re taught, repeatedly, to listen to the users’ complaints about your work, because they are the voice of someone struggling with what you’ve designed.

We’re taught that when people approach us with a solution, we should talk to them and draw the problem out of them before agreeing with their solution.

We’re taught that when people say rude or negative things to us in critiques, they may be speaking out of their own exasperation and lack of control; it’s not necessarily a comment on us, and we shouldn’t take it personally.

And it’s not just designers; content creators and coders learn the same things, too.


A coworker and I talked about the Sanders rally kerfuffle over lunch. “I wish people would just stop and think before they expressed their opinion,” he said. “Too many people on the Internet just talk without really pausing and thinking it through.”

He’s right. We don’t stop to think, to listen. Instead, it’s straight to the blogs and the Twitters because The World Must Know.

We need to shut up and listen. We need to understand the problem before we try to solve it. We need to remember that we specifically may not be the problem, but we collectively may be. And we need to remember the role we play in this society.

The time for writing and advocating and opinionating will come, but in the meantime, when the vulnerable and disadvantaged speak, we shut up and listen.

No one cares about your opinion. They just want you to listen to their truth.

The UX of a cheese sandwich

In Brussels, Yelp insists the best place for a sandwich is a hole-in-the-wall above the Marche aux Herbs named for its owner, Tonton Garby. The line never seems long... only it is, because his average transaction time is something like 10 minutes. His sandwiches are cheap -- 3-6€ -- and all cheese (good cheese, yes, but cheese nonetheless). But that's not why they come. They come for Monsieur Garby.

Garby insists, through many signs, gestures, and languages, that he wants his customers to be happy. He's careful about picking cheese, friendly to a level that makes Americans feel inadequate, and always quick to remind you that if you're unhappy he will give you your money back.

Also, his sandwiches are not half bad. Mine was chevre encrusted in pistachios, green apples, and local honey. It was heaven.


When I was a kid in Oklahoma, John F. Lawhon was a mainstay of local TV. He'd come on during the news and tell you this sofa set was $499 today only, so you better come on down. One day, he sold off his furniture empire and retired. The next day, he was already bored. So he started talking to his old salespeople to understand what made them successful, what made them different from the run-of-the-mill salesperson. The result was a series of books on retail sales that became the standard textbooks in many business college classrooms.

Lawhon's theory was based on the radical idea that a salesperson needed to identify what the customer needed, show them the options, and help them make a selection they would be happy with. The customer had to feel confident that they were the one making the choice, and that the choice was the right one. No high pressure, and no pushing them into this sofa or that. In fact, he found that the best salespeople never got to the “pitch” or the “close” — instead, they reiterated all the ways the customer’s selection was going to work for them.

Lawhon found that happy customers are the best customers: If they are pleased with their choice, they will return and buy again, and they will recommend him to their friends. Being known for selection, fair prices, and a great experience was better in the long run than raking in money hand over fist on deals that left customers unhappy.


In the user experience world, service design is all the rage. (No, service design isn’t new, but when applied to UX, it is.) The UX community talks of creating massive, deep, systematic experiences that extend well beyond the the pixel-pushing pigeonhole we've been crammed into. UX is way bigger than simple images, understand. It's no wonder the Disney MagicBand garners so much hype in the design world.

So now we show how users and personas participate in the overall process of a system, when they engage, how those engagements work. We talk about uniforms and physical spaces as much as databases and web experiences.

On the one hand, this seems like the right thing to do. We want big, engrossing experiences! Look at all the ways the MagicBand works and all the different interactions!

On the other hand… this thinking isn’t simple. Take the London Underground’s “reclassification” of stations. Some are gateways, places that expect lots of clueless tourists. Others are local, places where the riders know how the system works and need no help. From an Pareto 80-20 view of the world, this makes sense.

But what happens when a “local” station gets an influx of tourists? What happens when a “gateway” station is also a heavy interchange station and all that “extra help” interferes? How does the system flex and morph to handle those situations which don't follow the pattern?

What are people to the system? Personas? Or humans? Does the system treat each interaction as an opportunity to make the life of a customer better, or as a theoretical transaction between Walter The Station Agent persona and Sophie The Out-of-Towner persona?

I'm sure Transport for London has thought about this -- they're systems thinkers. But what about the rest of the design world? Do we think about the transactions that happen in our systems, or do we think about the people?


Garby focuses on simple, long interactions to promote customer happiness. Lawhon focused on simple, smart interactions designed to identify customers needs… which ultimately lead to customer happiness.

We talk of delight. We talk of service design. We talk of “user experience.” But what we really want is happy customers -- humans -- whose engagements with our creations are at once positive and seamless. 600 page reports and plotter paper sized user journeys can’t create that, only inform.

What can create it is focusing on those singular moments where a person, in need of something, receives it. Whether it’s support, information, or maybe just a “You look confused — how can I help?” inquiry, it needs to remain simple, real, and human.

Tonton Garby gets it with cheese sandwiches. John F. Lawhon got it with sofas. Do we get it with our websites and wearables?

The Design Seagull

The job was located in a historic Pioneer Square shoe factory. Pioneer Square is a bevy of 100+ year old stone and masonry buildings built on top of the ruins of the Seattle fire, and it sits, low and flat, against the waterfront.

The waterfront attracts seagulls. Seagulls love to perch. And one day I looked up from my desk next to the window and saw one, staring straight at me.

I took a picture and posted it in the organization's HipChat. “Design Seagull is here to critique,” I think I told them.

For the next company meeting, I used Design Seagull as a meme in my slide deck. We were a vastly understaffed design team for the work we needed to do — three major projects that probably needed a staff of four, and we were managing with two. Design Seagull became the de facto third designer, or perhaps, critique partner, practicing its own version of “swoop-and-poop”.

I posted one of those memes on Twitter, and it took off among my friends and acquaintances. I’d get sightings from window sills and patios all over town. Even a content strategist cat ran with it.

We had no connection, the seagull and I. Just two creatures staring at each other, one trying to understand how to make a new product hang together according to the roles and goals of its users, the other staring at this human and wondering if he had any old hamburger wrappers to poke at.

The seagull kept coming back, at odd times of the day, totally unpredictably. And it was the same seagull every time. Same red stain on the beak, same cleft in its right foot.

Design Seagull's random appearances made me think of a fox.

Years ago I stayed with some distant relatives who lived in the Derbyshire Dales. At random times of the day and month the fox would appear in their front yard, eat from a plate of food they'd laid out for it, and leave. Even though they had been putting food out for years, the fox would act high-strung as if it was some trap to be vigilant about.

This event, this appearance of the fox, was a piece of serendipity for them, a moment of the week to look forward to. A moment, perhaps, of delight. A bit like a seagull on your window ledge.

In the design world we throw around "delight" as some sort of magic pixie dust you throw on your website to make people "happy." Some designers ladle on highly informal language, cartoon characters, and other idiosyncratic cuteness in order to create it. Their work, though, leans on whimsy, and whimsy is not delight -- it can often be annoying.

Delight is another feeling altogether from whimsy. It's the serendipity of a fox appearing out of an arbor, a seagull landing on a window ledge. It's a moment when you realize the randomness of life, perhaps, isn't as random as you think it is, that lo and behold, something behaved in a way you did not expect, in a way that exceeded your expectations, and you felt good about it.

It's the form that fills out just the right information for you. The drudgery of paying bills simplified into a easy and painless process. The sense that, in the randomness of this world, a designer knew you were coming and set things up for you so you would not stumble -- and perform far better.

I took another job in late spring, moving into a building 18 blocks away and 100 years younger than that shoe factory. There are seagulls. But they’re not interesting. They don’t sit on a window ledge. They can’t be meme’d. They just swoop on the roof of the building next door and poop on it.

Perhaps they’re training to be CEOs.

Mon français maladroit

This summer, we’re spending a month traversing western Europe, and about half of that time we will spend in France.

My French is abysmal. My minor in college was in Latin, a language you only rarely speak. Reading French, a living, spoken language with many Latin cognates, was easy. Speaking it wasn’t. Mix in that I’m a visual, not an auditory learner, and it quickly became a personal nightmare.

Sophomore year of college, second semester French. My professor asked me to give her an indirect statement. I blurted out the only thing that came to mind.

Je sais que le poisson est mort.”
I know the fish is dead.

The professor shook her head in exasperation.

I’m spending two weeks in a country that speaks a language where the best I can do is acknowledge the demise of a fish.

It’s going to be uncomfortable. It’s going to be awesome. I’m looking forward to the discomfort.

Discomfort is something we actively try to avoid, but we regularly have to confront it. When you change jobs (a new company, a new division, or going freelance), you have to learn a new culture, a new domain, and new rules. Sometimes, you feel exposed as a fraud simply because you don’t know every single acronym they use in a company or an industry (or that three disparate things share the same acronym).

Discomfort is at the heart of design, of course. Great design relies on understanding how people use a product; how people use it is something that is difficult to observe directly and difficult to extrapolate perfectly to all users. This inexact observation exposes designers to criticism of their design (and process). And it hurts.

We hate being exposed, whether by lacking research, or by using skills and tools we don’t have the highest confidence in, or a lack of time to make something flawless. (Usually, it’s all three.)

But we have to feel the discomfort of being exposed. It’s only in the discomfort that we learn and grow our skills -- and ourselves.

Discomfort can also lead to empathy. The pain leads you to ask how things could be different for someone in your same position. I watch this all the time with new developers starting off in a company: They have to get their dev stack running so they can check in code. The process is usually painful and somewhat byzantine, but it builds a sense of suffering together. (The word compassion, after all, comes from the Latin “compatī” — to suffer together.)

We need to be uncomfortable. Running from discomfort is running from learning and growing as humans. We suffer so others do not have to suffer later. We hurt so that we learn how not to hurt again.

And so, into France I will dive, knowing that were I to encounter a dead fish, I would know what to say. For everything else, though, there’s “Parlez-vous anglais? Je parle seulement un peu du français. Oui, je suis un idiot américain.”

I’m not a cool kid. That much is true.

I never got to be in the upper crust of the social strata in school, so I was condemned to sit in the back corner of the cafeteria at lunch time, with the punks, and nerds, and hippies. I was a long way from the tables where the Cool Kids held court.

I spent the first part of my career buried in the back office of a university school quietly building out their website. I was both shy and arrogant, thinking I knew more than everyone I worked with, but too timid to raise my voice. Took me years before I found my voice in the wider community.

I read Meyer, Holzschlag, ​Zeldman, Krug. They wrote, they spoke at conferences, they were authorities. I wanted to be that. The first time I saw Jeffrey Veen speak, I thought, "This sort of storytelling, this is what I want to do."

I wanted to be a cool kid... like them. I started blogging. Eventually, I was presenting, too. I spent the next phase of my career finding my voice, first in the world of higher education, then in the wider user experience world.

At conferences and other events I started meeting some of my heroes. Outside I tried to be nonchalant, though inside I was thinking "OMG YOU'RE A MAJOR WEB CELEBRITY" and getting very fanboy. Sometimes it leaked through, of course.

One day at a conference one of these so-called Cool Kids walked up and introduced themselves. They knew who I was.

But I’m not a cool kid.

Put me on a pedestal and I’ll only disappoint you
Tell me I’m exceptional and I’ll promise to exploit you
-“Pedestrian At Best,” Courtney Barnett

The more I hang out with industry people, the more sordid the gossip I hear. Who hates whom, who is all about promotion and ego and power, who is really a nice and generous person.

I know a name in the industry that, were you to search their name on Twitter, will return a cascade of “This person is following me!” tweets in the results. Their "cool kid" persona is following others on Twitter en masse. For them, Twitter is not about conversation, it's about ego-stroking adoration.

I wonder how many others are out to cultivate a persona of adoration, or perhaps exploitation. We mutter about the people who seem to speak at conferences more than they do "actual" work -- the dreaded "thought leader" label. But most of those you see on stage are like me. We just say what we feel, and then we go back to doing the work we're paid to do. Our job is to inspire people and drive the conversation, but it doesn't pay our bills.

But the exploiters are out there, people too intoxicated by their own image, who need adoring acolytes to fanboy over them for their books and talks and thought leadership and pull quotes on Twitter. You can't always tell where the brand ends and the person begins, or if there's even still a human in there. 

Recently, though... the adulation is starting to happen to me. People come up to me going "OMG YOU'RE DYLAN," and I’m thinking “who is this person you’re talking about and can I meet them because they sound way more awesome than me.” The impostor syndrome wells up in a hurry.

But now that I've met the cool kids, I know they are just like me. They have their own human failings, their own self-doubts, their own mortgages to pay. The cool kids are just as scared as the rest of us underneath their prestige and cool swagger.

I've been incredibly lucky I've been given opportunities to do things I love, meet some great people, and maybe inspire a few others to do greater things. I have every obligation to return that luck by being helpful and gracious to those who come after me.​ Writing and speaking are just the ways I'm trying to pay down that debt.

I'm not a cool kid, and honestly, it's not my goal anymore. I don't think it should be yours, either. Focus on craft, on making others better, on improving this field and this web we've created.

Let's just hang out here back in the corner of the cafeteria and be punks, and nerds, and hippies. Let's talk about your truth. Let's talk about what you're passionate about, what you're afraid of. Put it in a blog, in a slide deck, a video, and post it on the web. Let's share and stop worrying about being cool.

I can also promise that more than a few people you think are cool kids eat lunch with us, too.

On Burnout and The Year Of Hell

I hate it when I miss things. And I missed the telltale signs of burnout in her.

She is a young designer with a lot of promise and loads of skill to back it up. I thought she would make a good fit for one of the best enterprise UX teams in town, so I made the connection between her and the company.

I met her the day after the big interview loop. And… there was the sign I’d missed. There had been an interview question she struggled with. It’s a fairly standard one in UX interviews, but it requires some finesse to answer if the corporate political environment impeded your ability to do your job.

The question nagged at her. It shouldn’t have. But it hit her squarely in the spot she was most burned out, and that sort of sting doesn’t sit well, nor does it fade quickly. She came back to it in that meeting and subsequent conversations.

She made it to the interview loop on her own merit. Her burnout betrayed her.

If I’d known her state, I would have prepared her differently, pushed her to tighten her story and pack away as much of the anger and pain as she could. Would it have helped? I don’t know. But I know it’s what got me through my own Year Of Hell.

***

I had watched my job turn into a death spiral. What started as a passionate reimagining of a cornerstone product quickly turned into an overwhelming experience that consumed me. We didn’t have enough designers. The development team was moving too slow. But I was heads down and stubbornly trying to drive the design through, so I didn’t notice.

Eight months into the reimagining I went to see family in Atlanta and had an awful time. My head wasn’t on vacation, even though I was a six hour plane flight from home. I was standing in the Georgia Aquarium when I got an e-mail saying a contract designer quit, citing how overwhelming the work had become. I loudly swore, not noticing the group of kids I was standing next to. I had become That Guy, the one who swears in front of your kids because he’s completely oblivious to the world around him.

I missed that sign. It was my own telltale sign of burnout, but I chalked it up to a bad vacation.

Burnout has a lot of symptoms, but I can walk through the list and tell you that I’d felt every one of them that year. My relationship with the organization had become so lopsided that it didn’t matter how much energy I was expending; the more I threw in, the less I got back. I felt increasingly disillusioned. I wasn’t able to sleep through the night. When I wasn’t feeling angry, I felt depressed; when I wasn’t feeling depressed, I didn’t feel anything.

Everyone else noticed, but I didn’t. They tried to warn me. I even had one veteran UX designer tell me, over several drinks, that I needed to abandon the field altogether. And yet, I soldiered on in a toxic environment when I needed separation from it.

Eventually, the death spiral was beyond recovery, and the best thing for me to do was quit. I turned in my resignation and shut down for a while.

***

I didn’t know if I would ever recover.

The damage felt irreparable. I was mentally exhausted and questioning everything I believed in. I felt I was standing in the remains of a tornado-flattened house wondering if I even should rebuild.

To find my path out, I turned towards something I had let go by the wayside during the years of burnout: I would try to reboot my creativity through writing.

I put together a plan: A month of blogging as much as I could on a set of topics I threw together. I called it The Month Of Blogging Rantily. I unpacked what went wrong with the job, how I lost a ton of weight in the Year Of Hell, and my philosophy on the job search I was spinning up. I tried washing out the toxicity.

I found new rituals. I decided during my layoff I would try to tour as many Seattle coffee shops as I could. There are… well, they are legion, and that’s just the Starbucks. I used the opportunity to drink coffee as an excuse to go write.

I went running in the afternoon, walking in the evening. I made a list of design and technical books I had put off reading and started devouring them.

The more I pushed myself creatively, the more my old creative self came back. Instead of the death spiral of diminishing returns the last job put me through, I was getting a return on what I was producing. People read my writing, commented on it, tweeted it. Reading books about UX confirmed that I wasn’t an idiot when it came to design, and it restored my hunger to learn more again.

When I finally signed on with a new company, I had occasional jitters, post-traumatic afterimages of the burnout. But the fear was gone. I was executing again.

What I discovered later is I had essentially done what I was supposed to do to build up my resilience. Through writing, becoming more realistic about my plans and goals, and building up my self-image and problem solving skills, I strengthened my ability to recover from a crisis — and started to identify how I got where I was, address the problem, and choose a different path.

***

Burnout is something pretty much everyone in the tech industry has had to confront (and if you haven’t, you will soon enough) — it’s a dirty secret that the tech industry and burnout are intertwined. We don’t want burnout, then we talk about the “9 to 5” coders and designers with disdain because “all they do is punch the clock.” We don’t want burnout, but we talk hustle. We don’t want burnout… and then we do.

Some people suggest “work-life balance” or “positive organizational culture” are effective preventatives for burnout. I disagree. Work-life balance and culture can help provide some organizational resistance to burnout, but you still see burnouts and people out of balance. So it’s only half the solution.

The other half lies within us. I think we can teach ourselves to fight back against the siren call of burnout, and we can do it by building up our resilience.

With resilience we form a better self-image, so the guilt of not working hard enough doesn’t win out over balance. We form better coping mechanisms, so the fear of not doing a good enough job doesn’t call us to work harder. We become decisive and self-reflective, so that we don’t forget that control our destiny and can learn from our past, good and bad, to make better decisions about our destiny.

Resilience is difficult to build up, since it’s less a “magic bullet” and more changing how you cope. The American Psychological Association offers ways to build it up; much of it comes back to taking care of yourself emotionally and physically and keeping a good perspective on the situation at hand. In a burnout situation, that can be difficult. Ultimately, quitting the job helped me regain my perspective and find my hope.

Not everyone is lucky enough to just walk away. If you feel like you’re burning out, talk to someone and get help.

***

My primary lesson from the dark days of burnout is to be honest and transparent, even if you fear that people will find out the awful truth. Sometimes you have to accept that you aren’t as good as you think you are, that you're a fool for thinking you could blithely avoid burnout by sheer will. Of course, in some cases, it also means accepting you're better than you led yourself to believe.

Honesty is difficult, though. I have people from my past trying to tell me, over and over, that I should not talk about how I fell apart. But let’s go back to the start of this piece.

I’m sitting in front of a designer who is clearly burned out. What do I tell her? Do I allude to my Year of Hell? Do I elude, wave my hand over the burnout and tell her to go find help? Or do I tell her the truth: That one year previous, I was where she was, and if I managed to climb out of this hole, she can too?

I decided to tell the truth. I wrote this piece you’re reading.

I know some notable and notorious people in the tech industry who have been through the same dark, burned place I’ve been. But they won’t talk about it, perhaps out of shame.

And still, I keep meeting young designers, developers, leaders who are suffering from a sense of burnout, and they’re feeling alone.

It’s time we told them the truth: It’s OK, we have been there, and we may be there again. And the only way to survive our years of hell is to remake ourselves as resilient people.

On Being Generous

1.

In the eulogies that came in the immediate wake of New York Times journalist David Carr’s death, people would come back to one adjective: Generous.

Young reporters talked of how Carr gave them direction when they were directionless. Friends posted the encouragement he gave them in dark times. Everyone had a story about some way he made time for them, whether an e-mail, a cup of coffee, or just his presence.

2.

Kristy and I were drinking beers in a Belltown dive and talking about the state of our careers. So many people are hitting me up for career advice, I said, and so many of them are succeeding with it that I wondered if I should bail out on my current career and go be a career coach.

“No, don’t do that,” she responded. “You’re doing what you’re supposed to do — you’re paying back by helping those that come after you.”

3.

I’ve seen a lot of fear in the tech industry, from the leadership to the rank-and-file. The fear of stagnation, displacement, or just waking up one morning and the ways of the tech world changed, again, for the 100th time in the history of the web. It’s not just impostor syndrome, but a fear of being left behind.

Take responsive web design. Five years ago, it was an interesting, but complicated idea that you didn’t need to know unless you were a bleeding edge designer. Now, if you don’t know responsive, you’re way behind the times.

For those who have been in this industry a while, we worry the kids are coming to put us out of work. So we keep trying to run harder and harder, learn more and more, and sometimes, push the new kids aside.

But craft doesn’t come from running harder. Craft comes from learning the lessons and building new ways of doing things from experience and iteration.

Craft is something we can teach the ones coming behind us. And by teaching craft to the next generation, we pay back those who came alongside us when we were young. And it can be as simple as passing an idea on.

4.

A few months ago a friend of mine asked me how I kept design projects organized and made sure the right information is spelled out for the rest of the team.

I have a method, of course: An Excel file which consists of spreadsheets I’ve created and collected over the years to bring order to the design chaos. Deliverables, personas, goals, user flows, user stories, they’re all in there. I sent him a copy.

He promptly adapted it for his uses by adding a tab for mapping out interactions across devices. It is now the standard method for organizing interactions and content at his employer.

And, his changes made my system better.

The lessons in craft we learn must be taught, so they can return to us as new lessons we can learn. If we treat our craft as open source and not hold it tightly behind personal NDAs and barricades, we collectively can build on each other’s ideas and make our craft better. Sharing is the only way we all get better at what we do.

5.

I am an introvert. Alone time is everything to me. And yet, I make the time to meet those who want to talk.

I was up on Skype at 6am one morning to help a young designer figure out what to do next. I had coffee on a Saturday morning with a front end developer wanting advice on transitioning into UX. I inundated another dev with Twitter DMs laying out how to find a better job (which they promptly did.)

Yes, it helps your ego when people come asking. But I probably learn more from them than they do from me. They help my craft. They help me iterate and remind me that I’ve come a ways on this journey, but I still have much ahead of me to learn.

6.

Are we frauds? Are we doomed to be found out? Yes, we most likely are. As much as we want to argue for a meritocracy, we got to where we are with some dumb luck, some coincidence and serendipity, and even some societal privilege.

David Carr closed his memoir of drug addiction The Night Of The Gun with this line:

I now inhabit a life I don’t deserve, but we all walk this earth feeling we are frauds. The trick is to be grateful and hope the caper doesn’t end soon.

Carr showed his gratitude through his generosity, and with it, he was bending the rules of the game. Advice and guidance and a listening ear are their own forms of luck and serendipity.

When people come to you for advice, what do you do? Do you dispense something pithy and get on with your day? Do you take the time to listen deeply and encourage them? Or do you guard yourself knowing that if others know your secrets they will use them to overcome you?

For me, I choose to ignore my introversion and exhaustion in order to be present any place, any time, anywhere with anyone who asks. I’m where I am because of dumb luck, serendipity, and privilege. The best way to keep the charade going is to let others in on it, so that they become accessories to the caper I’m pulling off — and I in theirs.

The Year Of Empathy

1.

I grew up in Oklahoma in the 1980s. It was not a great place for kids with high IQs, awkward social skills, or a lack of athletic ability. When you have all three, well, it’s brutal. I was called a lot of names.

Nerd.

Geek.

Dweeb.

Fag.

Spazz.

When you deal with that sort of emotional bullying every single day, you create defense mechanisms to deal with the wilting fire you’re under. You avoid doing things “nerdy” you might find fun — which is why I never played Dungeons and Dragons or other role-playing games. You change your behavior so people won’t see you as gay, even though you are very clearly hetero. You build a hard, spike-covered outer shell to keep away anyone who can hurt you.

High school… well, high school was a nightmare. To be friends with me was damaging to your social capital. Thus, I had few friends. The ones who did often had to publicly repudiate me to keep themselves from becoming pariahs.

When Columbine went down nearly a decade later, I just nodded. I had those fantasies when I was a kid, of walking into school and killing my abusers.

College was better, but only just. Still awkward, still smart, highly defensive. Other kids in my dorm wrote homophobic insults about me in the bathroom stalls. After an incident involving a bathroom sink meeting its maker at the hands of a violently drunk freshman, the hall director discovered the graffiti, ordered me moved to another part of the building, and threatened all members of the floor with eviction.

It says something that I barely even noticed just how abusive the language actually was.

2.

I didn’t even call myself a geek until I was 25 and living in the UK (a land that flies its freak flag in the same way the US flies American flags – as large and as high as possible). By then, I’d discovered the Internet.

The Internet, first in the form of the Usenet and then in World Wide Web, became my savior. There were people just like me out there. They had jobs. Spouses. Families.

My livelihood I owe to my devotion to the web. My career would move from coding to designing to guiding experiences.

But the sort of web geek I became was rooted in my days of bullying.

My affinity for accessibility comes out of this place of exclusion. You could say that being called “spazz” was a stepping stone to that.

I (regretfully) came late to support GLBT rights, but in 1992 I voted against Amendment 2 in Colorado — touted as “no special rights for gays” — because I had been called “faggot” so many times.

As for user experience, that came from the empathy that springs from knowing how it feels to be the one who isn’t in on the joke.

3.

I say all of this because, honestly, I’m tired of the bullying I see on the Internet. The intertwining of Gamergate with the Chan communities has led to so much doxxing, swatting, and general asshole behavior that whenever the battles stir up again I get wound up in anger.

And yet, these are, in theory, my people. Just as bullied, just as outcast. Why am I not with them?

At 22 I was an angry young man. At 42 I’m not as young, but I’m still angry. However, I’m not angry at those who ran me down, damaged my self-esteem, left me defensive, and led me to turn away from opportunities to find common cause with others like me.

I’m angry it’s still happening to others.

4.

This liberal, libertarian web that has evolved over the last 20+ years has been built by people like me, the outcasts, the “crazy ones,” the kids who spent more time with their computers and books on Friday night than drinking up in Chandler Park with the popular kids.

We were not the cool kids. And then, all a sudden, we were.

But our desire to get back at the cool kids is written in the DNA of the web we built. We built an open system that was meant to level the ground, give every person the opportunity to rise up and strike down the limitations of the systems that have held us down. The web is for everyone.

But now that open system, in the hands of both the powerful and the angry, has become a cudgel to beat down the weak. It has become a space where we don’t foster empathy, instead easily raising angry mobs to attack our now dehumanized “opponents” in behavior resembling sociopathy.

We view the design and code of the web as data points and impressions, not as wholly personal experience. We try to avoid it with personas and user research and accessibility, but then we return to our vacant metrics, to our manipulative A/B tests, to our inaccessible code we keep shipping because there’s just no time to make it functional for all.

5.

Eric Meyer’s direction change back in November reached me at a time I was ready to hear it. I had recently left a situation that had triggered flashbacks of the days of being bullied. Twitter was full of the sociopathic vitriol of Gamergate. It was time for a new message — of not just designing for crisis, but building a web that, to paraphrase an evangelical Christian concept, “meets people where they are in life.”

Sara Wachter-Boettcher’s heartbreakingly beautiful “Personal Histories” reinforced that for me. We don’t think of the consequences of our words and actions on real people in real pain. The parent, their child acutely sick, trying desperately to navigate a hospital website. The abuse victim, forced to come out as an abuse victim on a possibly ungermane form.

My daughter’s school has a program called Roots of Empathy. They bring in a teacher for elementary school kids to learn empathy from. The twist is the teacher is an infant (accompanied by their mother). During the program, the kids are asked to observed the baby’s emotions. Why are they crying? What is the baby feeling?

Through Roots of Empathy the children learn how to put themselves in the shoes of others, how to be more inclusive. Schools with Roots of Empathy programs have fewer incidents of violence and bullying.

How do we take the lessons of Roots of Empathy and transpose them to the web we’ve built? As developers, designers, and content creators we cannot control what users are carrying into their experiences with our work. They’re carrying past and present pain. We cannot pretend our users are perfect automatons, single data points on a web log devoid of emotion. We have to be kind. After all, we have our own past and present pain we’re carrying into the interaction.

6.

So, why did I not join the Internet brigades that are full of the bullied like me? After all, the psychic wounds are certainly not gone. The echoes and ghosts of the past are still with me. Why not?

Of all things, it was my 20 year high school reunion. Yes, I actually went to my high school reunion.

And there, with all the jocks and cheerleaders, I finally understood. Yes, my pain in high school was personal, but we were all suffering. All of us.

If I’d known back then, would things have been better? Would I have been able to reach through the strict social castes of school to say hey, I know you are hurting, and it's OK because I'm hurting too? 

I don’t know. But I wish I did. Or I wished I’d paid more attention. But that defensive shell wasn’t going to keep itself up.

But nonetheless, I was standing in a hot and humid Oklahoma summer night, and the head cheerleader was telling me she was happiest to see me at the reunion. And she wasn’t the only one saying it that night.

The years of bullying had dehumanized me, and it had dehumanized everyone in my eyes. I didn’t see how poisoned I’d become until that moment.

The web is poisoning us, telling us empathy doesn’t matter, insisting people who are WRONG ON THE INTERNET deserve our scorn and none of our humanity.

This year, we fight back. The web we’ve built needs to be patched with empathy, on every social forum, on every web form, on every piece of microcopy. This is the Year Of Empathy.

Let a thousand pull requests blossom.

Time to get a better job

It’s the end of the year, and you’re working on your New Year’s resolutions. You know the ones. The ones where you go “oh hey, I’m going to fix MY ENTIRE LIFE in 2015!” The ones you will abandon by the first of March… at the latest.

Well, I’m going to help you with one of them. I’m going to help you get out of that crappy job you’ve been telling yourself you were going to leave for months or years.

Get OK with leaving.

Some of us are change-adverse. I know I am. I order the same double tall nonfat mocha (no whipped cream) every weekday morning, and it’s such a constant every barista in the place knows it. It’s a pattern I keep to help give my work day structure.

Patterns are easy. Patterns are simple. But patterns lie to us. Even if the pattern is terrible, you don’t want to leave it. It’s a known. It's comfortable. Your boss underselling your work constantly? Well, that’s a pattern, and you get comfortable.

No one who can get another job should stay with a crappy job. Just, no. You owe yourself better than that.

Get OK with leaving. There’s something better out there. Better could be healthier relationships with coworkers, or more opportunities to learn and grow. It will not be comfortable. But it will be OK.

Get real about yourself.

When I started this last job search, I armed myself with something called The Job Decision Matrix, an idea I got from Seattle-area executive Charlie Kindel. He advocates stack-ranking everything you want (and don’t want) in a job, everything from location to The people you want to work with (in my case, I have a “no assholes, no bullies” rule I live by).

I built it out in Trello and used it religiously during the job search. It kept what I want in a job in focus. As a visual thinker, I could recall the board in my head as I interviewed.

It also helped me define what I’m good at, what I need to improve on, and what I should avoid doing. (I know to avoid jobs heavy on visual design, for instance.)

Once you decide what you want to do, configure your LinkedIn profile around it. Cut the stuff you don’t want to do. Same on your resume.

The value here is understanding what you want and what you can offer. You need that focus, so you don’t throw yourself at jobs that are above or below you — or jobs you know you’ll hate later.

The job search, after all, is a sales job. You’re marketing your skills, then trying to close the deal in interviews. Know the customer you’re looking to buy your talent, and know you have the talent they’re looking for.

Find the right place to interview before you interview.

During my last job search, I came up with an idea I call “coffee dates.” Instead of agreeing to a full interview loop, I would instead sit down with someone at the company who understood the job requirements — the recruiter, the hiring manager, even an executive — and talk through what we could offer one another in the role.

If the fit was good, then I’d come in for a full interview loop. If not, we were only out 30–60 minutes of our lives, and they’re just out the price of coffee (unless I bought it, which happened more often than not). Oftentimes, I could help them clarify what it was they wanted in the role and what sort of person they should go after.

I’d rather “waste” an hour of my time helping them find the right person for their role than waste hours of interviewer time on an interview loop that clearly isn’t mutually beneficial.

These “coffee dates” were like actual dates. Who are they? What do they do? What are their goals? What’s their ideal person? Do they exhibit any nervous tics that put me off? Are they generous and kind to the barista? Are they assholes or bullies?

I don’t like wasting my time. But more than that, I don’t like wasting anyone else’s time. We’ll all swamped in work, triple-booked on our calendars, with our heads in a thousand other places than here. I want to avoid time-consuming interview loops that result in a no-hire or a no-thank-you. There’s just no time for that in our lives anymore.

Do your reconnaissance first. Identify the sort of places you want to work. Find people inside the company to talk to who can speak to the open role. Take them on a coffee date.

Reverse-engineer job descriptions.

Use the job description to reverse-engineer what they’re looking for. Identify the ways you satisfy those requirements. Emphasize those needs and how your experience satisfies them in your cover letter. (You do still send cover letters, right?)

Be able to mix and match pieces on your resume for each job. Not every job has the same needs, so build your resume from interchangeable parts you can sub in and out based upon the job description.

Research, research, research.

Glassdoor. LinkedIn. Google. Find people you know who have worked there (and get people who work there now to refer you). Ask people in the industry what the buzz is around them. Identify their problems. Figure out how you can help solve them.

Learn to tell your story better. Amazon’s interview process is heavy on what’s called the STAR method — Given a situation, what tasks were you responsible for, what actions did you then take, and what were the results?

Come up with three good stories like this from your experiences. Be able to deconstruct things. Be very specific about what happened.

More than that, make those three stories relevant to the company and the role. A story about designing a new feature focuses on the prototyping work I did when I am interviewing for a role looking for prototyping skills. However, when I’m interviewing for a UX designer role, I’ll focus more on the process of getting the design from initial ask through research to wireframe to code. The outcome was the same: A successful feature.

While you’re at it, find one of those lists of “popular interview questions.” Dump it into a Google or Word doc. Get a work story to answer each one. Memorize as much of this as you can. This is now your interview playbook. Half your questions are answered, so you can focus on the hard questions and interviewing the company.

Flip the script on interviewing.

I see a lot of people who walk into interviews and hand all the power to their interviewer. They focus far more on making the interviewer like them than on determining whether the relationship would be fruitful.

Yes, the job search is a sales job. You’re selling your brand. They’re buying. But they’re also selling you on their brand.

A job is a contract between you and your employer — not just a financial contract, but a social one, too. You’re selling your work, but they’re also selling you on continuing to provide them work. The hiring process is expensive (in money and time) and they hate doing it over and over.

Do not hand the interviewer power over you. Instead, focus on finding the right job and organization for you. Focus on forging a mutual relationship.

Ask better questions.

At the end of every interview, I would ask a couple of these questions of the interviewer:

“If you could change one thing about this organization, what would it be?”

“What do you think the organization’s core values are?”

“Tell me about the last time you worked more than 40 hours/week to get something done. What was that like?”

“Explain to me what you think the core responsibilities of the job are.”

“A year from now, what would you expect to see me do if I were successful in this position?”

“Talk about a recent misunderstanding here in the organization. What happened, and how was it rectified?”

Notice something about these questions: They’re all open-ended. And they look suspiciously like questions they will ask you in their interview.

Flip the script. Make them talk to you and sell the company to you.

Practice, practice, practice.

Find a way to get some interview practice in, even if it’s just asking friends at other companies for an informational interview. Or apply for jobs you can get an interview for, but would never accept a job for.

This doubly goes for positions where you’ll be coding. Know the drill: You will be asked to code, so get used to the whiteboard. Try out sample coding questions.

Hone your answers. Get the practice in, and you’ll totally rock it when you finally identify that job you want.

Be retrospective.

I’ve adapted Agile Scrum sprint retrospectives for interviews. Within a day after the last chat session, I sit down and ask the three retrospective questions:

  • What went well in that last interview?
  • What could you do better?
  • What’s the one thing will do differently next interview?

I try to walk through every part of the interview loop and identity the adjustments I need to make.

It’s about not letting getting sunk in the neurotic handwringing of “woulda-shoulda-coulda” I get into after a poor (or even a good!) interview loop. Instead, I’m being proactive and adjusting. Just as football players watch film and see what they need to adjust, I’m watching my mental film of the interview to find my adjustments.

Your turn.

If 2015 is the year you finally promised you’d get a better job, get to it. Something better is out there, but you have to find it. Figure out what you want and get to looking.

Happy Birthday, Dad

My father would have been 68 years old today.

His father was a doctor, a WWII navigator with signs of PTSD, and son of a stern Baptist preacher. His mother was the daughter of an orphaned Cherokee girl and a West Virginia oil speculator who married her for her mineral rights (and they promptly got very, very rich).

My grandfather tried to get a medical practice going in Tulsa, living under the shadow of his wealthy in-laws and his own med school debt. By the time my father was in grade school, my grandfather, stressed out and fed up, ran off with his secretary. Their divorce was so contentious that it ended up in the state supreme court.

My father carried multiple shames from that. He was a child of divorce in a time when divorce was still uncommon, still a stigma. He felt blame from his mother for what happened, and from that blame, a desperate fear of not living up to expectations.

He did what any kid would do to cram down the blame: Partied hard through high school and his first year of college. Then came the Gulf of Tonkin. To keep himself out of combat, he tried the Coast Guard recruiter, who promised him that he'd spend his tour of duty patrolling the East Coast.

Unfortunately, my father didn't think to ask which country that would be the east coast of. So off he went to Vietnam.

Improved by military life, he came home, went back to college, got two degrees in architecture, knocked up his girlfriend (with me), got married.

He was a serial entrepreneur of an architect. Started firms. Left firms. Joined firms. Built firms. He would work 50, then 60, then 90 hours a week.

Dad never stopped thinking he had to prove himself. He carried his shame and pushed himself hard. He was also a heavy smoker and had been since he was 13. He didn't take care of himself. (Yet he quit drinking cold turkey.)

We never saw eye to eye. Driven, argumentative father; petulant, spoiling-for-a-fight son. I went to the University of Colorado instead of the University of Oklahoma partially to spite him. (Almost every member of my family has an OU degree. I at least had the common sense, though, to not go to the University of Texas and risk being run out of the family.)

I would be told, in my exuberance of youth (which, let's be clear, was so tame that Baptist kids would think I was square), to use my common sense, to stop being so lazy, to get a direction in life.

One Sunday morning in January 1994, I was working my college job when I got a message to call home.

Dad had been working, of course – his 90th hour of the week, a Sunday morning where he went in to the office at 4am and came home at 10am. As he walked in the door, he told my mother his back hurt and he was going to take a shower. In the shower, his aorta blew out. He was 47.

In the twenty years since, I've thought a lot about him. I have lived in fear of his workaholism, even as I have fallen into the trap myself. I feel the same fear of not being good enough that he passed down to me.

But I know he loved me. He did the best he knew how to do, given his fractured family, his lack of a real father, and his struggles with communicating it to us. He would never let me down, and he fought hard to keep our family together during some very, very rough times.

And he was an architect. I resisted being an architect. I was not going to follow in his footsteps, not into his 90 hour work week. I limped through college, changed majors twice. No common sense, no direction.

Then in my final semester, I discovered Mosaic, and with it the World Wide Web and HTML.

20 years on, I am an architect – of web experiences. Like him, I design spaces, draw boxes and lines, try to get managers and builders rallied around building things people will use.

I still feel the pull of the work. I feel the call to prove myself with the work, to prove that I'm not lazy.

I did not want to be my father. And yet, I became him, in my way. I am haunted by the fear of becoming him, and yet I have the same drive, the same loyalty, the same need to prove myself at every moment. On the one hand, it's made me pursue unhealthy work environments and my own long hours. On the other hand, I inherited that chip on his shoulder. That desperate need to prove myself made me who I am.

In my iPhone I have a reminder set for the fall of 2019, the day I will outlive him. He made me what I am, but I will not be him. Yet in the end, that's exactly what he would have wanted.

Happy birthday, Dad. I'm sorry. I love you. And thanks.

My friend Wendy remade herself a few years ago. Facing a number of intra- and inter-personal struggles in her life, she announced Wendy 3.0, a new operating system aimed at identifying and fixing her “wetware.” (My personal favorite new feature: “Decreased number of cycles wasted on worrying about what other applications are processing.” If only that were compatible with my personal OS.)

This year I attended her birthday party, aka the “release party” for the latest point version of her personal OS (4.3). Since she first announced 3.0, shes remade herself, from changing jobs to buying a new (and very nice) couch. Her “Master Plan” has come together well.

But we also know that “Master Plans” do not work for designing ourselves. We announce our Master Plan to Lose 40 Pounds, only to be face down in the Potato Salad Of Failure eight weeks later. We declare that This Is The Year We Will Quit Smoking, and by March were back to burning our lives away. Changes are a struggle for us to make.

One thing Wendy did was investigate different ways to patch her problems. An introvert by nature, she chose to engage with people in new and different ways – and discovered that as an introvert, she needs downtime. Her changes were small. But the small changes, combined with the insight that comes from retrospective, resulted in a large transformation.

The scientific evidence shows that small changes lead, over time, to large transformations. One study found that a “small changes” diet plan led to greater weight loss among participants than those on a standard plan – and that weight loss was sustained after the study ended. Even just taking care of the little issues makes a difference – A 2013 case study showed that dealing with the “small, annoying problems” improved quality of care in a hospital ward.

For myself, I have struggled with getting over my haters. Years of being constantly bullied in school left me super-defensive, prickly, and hard to get to know. Changing all that has meant fighting 42 years of bad internal programming. You're trying to patch your wetware, but a single change is like internationalizing an pre-existing, unabstracted codebase – thousands of spots where you'll need to rip out code and replace it, and in every place it still exists contravenes your instructions to not do it that way.

But the small changes seem to work. When someone says something that would raise my hackles, I ask first if they actually meant anything by it. When someone compliments me, I try to say “thank you” instead of bracing for the put-down that once always followed.

Isnt it odd how the things we tell ourselves about life – make small changes, experiment, fail quickly – are the same things we tell ourselves we need to do as developers and designers? And yet, so often we fight it in code. We want well-laid plans. We want waterfall. We want The Plan.

But its small changes that, piled one on top of another, allow us to climb towards transformation.

The loneliness of a middle distance designer

1.

A day before my 42th birthday, I ran a 10km race for the first time in my life.

To get to that race took a lot of work. I ran three times a week for months, during one of the hottest summers in Seattle history. I dodged SUV sized baby strollers and perambulating elders enjoying the view rather than crushing personal records.

I was happy with my result: 60 minutes, 4 seconds. Among my age group (40-49 year old men) I finished in the top 10. I ran the whole way, I didn’t get injured, and most of all, I finished.

But I was also unhappy with my result. I could have finished in under an hour, were it not for a set of mistakes I’d made on the journey to that race.

And as I thought about it, I realized I was confronting my old bugaboo, Hustle. (For the sake of clarity, “hustle” means the long hour, high energy work that is lionized in the tech industry and elsewhere.)

2.

The first lesson I learned when I started running was that what we call hustle was counter-productive to distance running. If you ramp up your miles too quickly, muscles and ligaments you’ve never heard of start to hurt. When they hurt, you start favoring one leg or one hip over another, which puts stress on another muscle or ligament you’ve never heard of.

This cascade of failures continues until something bad happens to a body part you HAVE heard of, usually from a sports report about a ballplayer that’s sidelined for weeks or months. Not taking rest days increases your chances of a bad injury even more.

So instead of hustle, you work on your stamina. You add a little bit of mileage every week, slowly, even if that means you’re shutting it down before you really want to.

I had ramped up too quickly. Soon parts of my legs I’d never heard of had issues. So I got a running plan, slowed down my progress, and built up my stamina. The pain settled down, and I ran my first 5K last October, finishing in under 30 minutes.

3.

But what happens, after all this gradualism, when you do “hustle?”

About a month before this 10K race, I went out for the office’s ultimate frisbee team. I hadn’t played ultimate since college, and the office team is loaded with elite team and former college players. I was going to have to step up my game.

Ultimate is all about sprinting: Running to get away from the defender marking you, then running with the defender when they take off down the field trying to get away from you.

So I hustled. And hustled. Three-quarters of the way through the game, one of my hamstring muscles had enough of the abuse and seized up.

I wasn’t ready for all this sprinting. And now, it looked (and felt) like all that work to run a 10K was gone in a moment of idiotic “hustle.”

Luckily, resting, slowing my pace, applying ice packs, and warming up before the race were enough to get me through all 10,000 meters. But it did slow me down.

4.

On race day, I made a final crucial mistake. I messed up my first mile, and it wrecked my final mile.

See, when you go barreling across the starting line, you’re in this big pack of people, many of whom are going at a pace slower than you would like. You get antsy. You have to get out of traffic. You want to start sprinting. But your inner voice keeps reminding you, “No, don’t do this! This is adrenaline and nerves. Stick to your pace. Slow down a bit. Save something for the last mile.” 

I didn’t listen. I pushed out hard through the opening mile and plowed ahead of the pack.

When I reached the closing mile, I was exhausted. People I’d passed back in the opening mile were cruising past me. I wanted to go all-out for that last distance, but I didn’t have it in me. It was a painful labor.

With distance running you must teach yourself pace. The heart of learning pace is teaching yourself what you already know you can and cannot do. You run at a slower pace early in the race, holding in check your competitive need to be out in front. You run slower earlier so you can run faster than everyone else at the end of the race -- and not feel like you’re running through maple syrup that last mile.

5.

Two years ago, I wrote a piece called Hustle Is Hype. It’s bounced around the Interwebs, and it even spawned a counterpoint.

Right after writing that blog post, I ended up in my own “hustle” project rethinking my employer’s core software product. And my work on that new product, underresourced and underfocused, turned into the very hustle I had criticized.

When you choose to hustle, the feeling of “doing important work” is seductive. It’s like tearing out of the pack of runners in that first mile. And you keep running. And then you’re tired. And then you’re burned out (and possibly sunburned). And then you somehow drag yourself across the finish line and ask yourself where it all went wrong.

Not every piece of work is as conveniently boxed up as a competitive run. The product redesign had a constantly slipping ship date, like a 10K that turned into a marathon that turned into the Western States Endurance Run. By the time the product had shipped, I had burned out on the project, left that job, and taken another one.

So, why hustle? Why do we choose to sprint when we should be thinking about building stamina and endurance?

Because it makes you feel good. It’s a drug, that rush of satisfaction that comes from a shot of adrenaline.

But like a drug, too much is not a good thing. So we must learn pace. We must learn, as Wren Lanier put it a few days back, that “stopping at the right time is the best way to avoid getting stuck. You can come back fresh each day, build momentum, and actually get things finished.”

So choose to stop before you’re tired. Make your design and development projects about finding pace, taking rest days, and building up your endurance. Focus on delivering consistently rather than on constantly hustling.

Hustle makes you feel good. Stamina lets you outlast the hustlers.

On communicating design

The wireframes looked good. But the story wasn’t there.

I stood there looking at the flow diagrams, the mockups, the outline numbers and details and boxes and arrows, and it was hard to follow.

“Can you tell me the story?” I asked the designer.

The designer rattled off the story, pointing out the boxes and arrows and detailed drawings and the outline numbers that cross-referenced to the flow diagram, running around between the mockups stuck to the wall.

Yes, the story made sense. The user flow felt right. The research backed it all up.

But.

I couldn’t see the story. Instead, I saw sheets of paper stuck to a wall.

So I called over a developer, one who’d be working on making the design into a reality.

“Can you tell me the story?” I asked her.

She looked. Stared. Squinted. Looked at the flow diagram, pointed to some things, and said, “Well, I think....”

She trailed off.

“I think this happens. Then this happens. But maybe not... shouldn’t that happen before this? Wait, why are these outline numbers here? What’s this diagram for? Do these wireframes run across the wall or down them?”

She couldn’t tell the story. Her version was as jumbled as those pieces of paper stuck to the wall seemed to me.

“I’m not out to embarrass you,” I told the designer later. “But if the person who is going to build your design can’t tell you what you’re asking them to do, then there’s a communication problem you need to solve.”

My own designer's arrogance

Early in my transition from web generalist to UX designer, I switched from designing in HTML to creating wireframes. With wireframes you can turn out design iterations quickly, providing “just enough” information to explain the idea you’re trying to communicate.

I worked for a company where the engineering team held great power, so I was in a symbiotic relationship with UI developers in pair programming and design processes. I was sending out designs and markup and getting back running code and feedback. Developers could just about finish my sentences. They knew exactly what I was saying on every wireframe.

But every new developer we hired had to adapt to me and my language. And that became increasingly time-consuming for me, increasingly confusing for them. One day, one of the devs went rogue and didn’t follow my wireframes and my stories. They didn’t think I was delivering the system they thought the user needed, so they stopped listening.

Looking back, I can see that “designer’s arrogance” got in the way of my empathy. I was so headstrong about creating right design for users that I had forgotten to communicate the design to the people who most needed to understand it – developers and product owners – in a way that they could understand why.

The UX of our UX

“Who is the user? What are they trying to accomplish? Why are they doing it?” We repeat those questions, over and over, when presented with the latest design challenge. The who, what, and why help us figure out the how.

But once we have the how, we struggle with communicating the how to the users who will execute on it.

We forget to UX our own UX.

Who is your design’s consumer? What is their goal? Why are they doing it? And how are you going to help them fulfill that goal?

Every deliverable should tell the story. But more than that, it should tell the story in a way that the deliverable’s consumer – whether a developer, a product manager, a content strategist, or an executive – can understand the story and their part in fulfilling the story.

For a developer, clarity on how to execute on the design. For a product manager, the ability to trace the path from the problem statement through the requirements and user stories to the design solution. For a content strategist, an understanding of how the design informs the content needs – and how the content informs the design needs. For executives, the business value of design.

The need for clarity in communication is a crucial first lesson not just for the newly minted designer, but also for the new developer, too. Undocumented and underdocumented code litters the codebases of a universe of sites and applications. I’ve watched dev teams fight with product owners over the value of a piece of technical debt that needs paying down – because the dev team can never explain exactly why the organization should pay it down, much less why the check needs to be cut now.

Design is communication. Code is amplifying that design so the world can see and hear and interact with it. Know your audience. Know their language. Communicate, communicate, communicate.

Our ten years of creativity

Earlier this year my daughter and I saw The Wind Rises, Miyazaki’s “last” animated feature. The protagonist Jiro, who designed the Mitsubishi Zero that gave the Japanese air superiority early in WWII, constantly dreams of the Italian planemaker Caproni. In one dream, Caproni, standing on a biplane wing with Jiro (because, after all, dream), says:

“Artists are only creative for 10 years … we engineers are no different. Live your 10 years to the full.”

Those words hooked into me. I ruminated on them quite a bit. Was he right? Do we have only 10 years? And if so, have I wasted them?

The longer you work in a creative field like the web, the more you worry your best days are behind you. The industry is ever-changing, and keeping up with those changes is as much part of your job as the day-to-day tasks of designing and developing websites.

I’ve worked on the web in some capacity for 15 years. I started as the equivalent of the mailroom guy for a startup — I encoded Word docs into HTML in the days before the CMS. I morphed into a web designer during two site redesigns. Then into a web lead. In higher ed I came in as a webmaster. Which became web producer. Director of web communications. And that transformed into user experience designer for an enterprise software company. From turning Word into HTML to turning Excel and Balsamiq into HTML.

So out of those fifteen years, which ten years are my creative peak? My ten years at the University of Washington, where I took a small school website and pushed it beyond what anyone thought it capable of? Or my ten years as an experience designer, where I first evolved the school website to a content portal for public health, then laid the groundwork for an enterprise software company’s UX team?

Or perhaps it’s not even in this field. Could it be my ten years as a father, as I’ve watched my daughter go from a small, grumpy handful into the bright, cynical future scientist and artist she’s turning into?

My peak as a web designer might have passed. My peak as an experience designer (or a father) may still be to come. I just don’t know.

I recently interviewed at a large software company, where their interview methods are prescriptive, but brilliant at digging out a candidate’s potential value to the organization. The questions focused on innovation, the ability to execute, and whether the candidate could improvise a good solution then iterate it into a great one.

The interview loop showed me all the ways I’d been reinventing myself every single day. Every story I told showed I was always innovating to solve problems — that’s the heart of creativity. Every new turn taught me something new, gave me a new way to use a tool I hadn’t thought of, offered me yet another opportunity to prove my worth. But to do so required reading, practicing, creating, over and over again.

It’s a cycle, a constant cycle, through which we reinvent ourselves.

Creativity isn’t like athletic ability. It doesn’t fade as we get older and our body betrays us. Instead, it is constant reinvention, constant renewal, transiting back and forth between the death and life of ideas, concepts, careers.

We are constantly traveling in this cycle, working between breathing in creativity and exhaling out creativity. But it’s like oxygen. Breathe out too much, we start to turn blue. That’s burnout. So we must constantly renew the creativity, and we constantly need to reinvent.

I look at my daughter, who, coincidentally, is 10. Clearly, her ten years haven’t arrived yet. But I’ve watched her grow and change, a child of this Internet age, constantly referencing YouTube videos, Nyan Cats, and Warrior Cats. She’s showing her art skills. Her poetry has a maturity I’ve never seen in a tween. But she’s already reinventing herself. She wanted to be a vet when she was 5. She wanted to be a programmer at 9. Now, a video game designer. One day, she will pick her vocation, her first one, and go. I have few doubts she will have successes and defeats, just like I have. But those 10 years haven’t arrived yet.

I think we may well have those 10 years. But I’m not sure they’re consecutive. Or even within the same field. Or maybe the clock resets every time we change fields, change vocations, change mediums.

Maybe that was Miyazaki’s point — he never stopped changing, never stopped reaching, never stopped reinventing. He just kept on creating. And he never lost his whimsy.

I hope I don’t.