Wren is a designer with a passion for creating beautiful digital products. Since she started working on the web over 12 years ago, she’s done a little bit of everything—from advising startups on UX best practices to pushing pixels for Fortune 500 companies. When she’s not pushing pixels, Wren co-organizes bill conference, an unconference for people struggling with the fact that “ideas are easy, making things is hard.”
For my last post to The Pastry Box, I wish I could offer a tidy lesson that I’ve learned from 2014, some sort of new wisdom or revelation that I will carry into 2015. But my life, just like my work, is perpetually messy, and I won’t pretend that I can string my experiences into a meaningful narrative.
Instead, I want to share a few of the things I’ve read this year that had the greatest impact on my life. Whatever small bits of wisdom I may have acquired in 2014, 90% of it came from thinking about the following links. Taken together, they tell a story more powerful than anything that I could tell.
The Importance of Donuts - Lara Hogan
Early this year, Lara Hogan wrote about the importance of celebrating her professional accomplishments in a tangible way – in her case, by eating a donut. Like Lara, I often feel like I’m not accomplishing enough, and while that can sometimes add “fuel to the fire,” over time it wears down your confidence and your enthusiasm for new work. For anyone who wakes up each day feeling like they start “at zero” (and I am definitely one of those people), this is an important – and potentially tasty! – step on the road to remembering your own value.
Sound of Summer - Chloe Weil
I never got the chance to know Chloe Weil, but her death this year was a painful reminder of how the Internet can help bridge the spaces between us, and yet the mysteries of the human heart remain—cavernous, infinite, and sometimes, impenetrable. Looking through her site, I fixated on her project Sound of Summer, in which she catalogs the music she links with certain times and emotions. (Chloe also had synesthesia.) It is a beautiful and well-documented piece of work, and I return to it from time to time both to discover new music and to remember the amazing woman who created it.
Trouble at the Koolaid Point - Kathy Sierra
Looking back, I can’t believe it’s less than 3 months since Kathy published what was, to me and to many women I know, an inflection point in the way we think about our careers & our participation in online life. She gave words to her own experience, and in doing so gave us a language to talk about things we hadn’t known how to share before. Her thoughts are so incisive they seem as though they’ve always existed, and yet they continue to reverberate through our industry and will, no doubt, for years to come. Thank you, Kathy, for everything.
Ditching Twitter - Erin Kissane
Nearly a month before Kathy’s article, Erin Kissane ruminated on the increasing emotional cost of being on Twitter. Along with Frank Chimero’s From the Porch to the Street, her thoughts crystalized so many of the difficult feelings I’d been having about social media this year. Mandy Brown picked up the same themes in October, writing in A Working Letter, "I realized, when reading Kathy’s post for the third or maybe it was the fourth time, that I had silently committed to an exit strategy. I am going to leave Twitter. Maybe not right away, but eventually. Maybe soon."
This idea of an exit strategy has resonated with me ever since; not just from Twitter, but from tech itself, and I know that I’m not alone.
Stay connected to your Internet friends - Val Head
A year ago, I moved away from my friends and community in Richmond, Virginia. I miss them, and although I’ve made lots of new friends in 2014, they don’t live down the street or even across town from me. Thanks to Val, I’ve gotten better at keeping up with the people I love, whether it’s via text, Skype, or Slack. It’s amazing how much that human connection every week can improve your life.
It’s been a long year for women in tech. But for many of us it’s been a long decade, a long career—an entire lifetime, really, of dealing with the bullshit that comes from being a woman who dares touch any device more complicated than a vegetable peeler.
When you are a woman interacting with technology, you are always doing it wrong. You are using your iPhone wrong. You are using your Android wrong. You are using Windows/OSX/Linux all wrong. If I had a dollar for every time a man sat down to use my laptop and said something like, “Jesus Christ on a pogo stick! How do you even function like this?” I’d have enough money to buy a Barbie Dreamhouse and hack it full of Arduino.
(No, I haven’t upgraded to Yosemite yet. Get over it.)
It’s no wonder so many women will say that they’re “bad with technology.” They weren’t born that way; they were made that way, throughout their lives, by a series of people who told them — loudly, heatedly, aggressively — that they were doing it wrong. Learned helplessness is a natural response to adverse stimuli, and when you’re female even the smallest gesture towards technology – such as reaching for the remote control – is likely to bring a world of hurt down on your head.
So let’s try something new, shall we? Here at the holidays, while you’re visiting with friends & family & loved ones, don’t make any person, of any age or gender or OS preference, feel bad about how they use technology. Not one single one.
Even better: find an opportunity to tell a girl that she is awesome at technology, because she is hearing the opposite message every day from about 1,000 different places. Don’t make fun of her if she’s playing Kim Kardashian: Hollywood. Don’t bemoan the state of childhood or tell her she should be playing Minecraft or GoldieBlox instead. Give her support and allow her to develop confidence in her technology skills and choices, even if they’re not the ones you would have made.
Whatever you do, don’t tell her that she’s doing it wrong. We’ve had quite enough of that, thanks.
My natural work habits are pretty terrible. I’m prone to distractions, easily paralyzed by insecurities, and generally prefer napping to almost any other activity.
One of my favorite ways to avoid doing work is to read books about work. This allows you to lie in bed and absorb the wisdom of someone else’s labor, which leaves you with a satisfying sense of accomplishment when you’ve actually done almost nothing. I highly recommend it.
I especially love books by writers about writing, because reading them allows me to maintain the fantasy that one day, when I’ve attained enough wisdom, I’ll write the Great American Novel. But until then, I’ve picked up a few useful lessons that I frequently apply to my work as a designer.
1. Embrace the shitty first draft
Our industry loves perfectionism. Every agency and startup is looking for a rockstar-unicorn-ninja designer who’s “obsessed with pixel-perfect details.” It took me a long time to realize that the dark side of my perfectionism is procrastination, and that the fear of creating something bad or ugly is an obstacle that keeps me from getting work done.
In her book Bird by Bird (possibly the most frequently recommended book about creative work of all time), Anne Lamott lays out the damaging effect perfectionism has on our creativity and mental health and urges writers to keep writing until they complete a first draft, no matter how poor its quality.
“Perfectionism is the voice of the oppressor, the enemy of the people. It will keep you cramped and insane your whole life, and it is the main obstacle between you and a shitty first draft.” - Anne Lamott, Bird by Bird
When I catch myself procrastinating and avoiding work on a project, I remember the power of the shitty first draft. Just sketch something. Draw a rectangle. Draw another one. Put the pieces on the board. Move them around. No one is watching your notebook or your Photoshop file. Don’t be afraid to make something crappy—you can always improve it later.
2. Spend it all, everything you’ve got
Like a lot of kids in the 80’s, I used to collect stickers. I had hundreds of the coolest, sparkliest, puffiest stickers—and almost all of them stayed on their sheets, unused, waiting for some magical future when the perfect sticker opportunity would appear. I’d admire them and think, “I don’t want to waste my stickers!” And I never did. I’m sure they’re still sitting in a drawer somewhere in my childhood closet, their sparkles hidden from the world. How sad.
We often want to hoard our best creative ideas; we’d rather save them for that amazing future project (which will be perfect and make us rich & famous) instead of spending them on the boring work we’re doing today. Like our favorite stickers, we don’t want to waste them. But treating your good ideas like a limited resource is a self-fulfilling prophecy; the less you use them, the fewer you’ll have.
“One of the few things I know about writing is this: spend it all, shoot it, play it, lose it, all, right away, every time. Do not hoard what seems good for a later place in the book, or for another book; give it, give it all, give it now. . . . Something more will arise for later, something better.” – Annie Dillard, The Writing Life
Have faith in yourself and your creative powers. Don’t leave your sparkly ideas in a drawer for later; spend them now and trust that something even better will come along.
3. Stop before you run out of ideas
Starting from nothing is always the hardest part of any project for me. Those moments when I don’t know what I’m doing or making are the devil’s playground, and likely to attract all manner of demons: fear, idleness, distractions, procrastination. Without momentum, I can get derailed for hours.
Hemingway offered this advice to young writers, “The best way is always to stop when you are going good and when you know what will happen next. If you do that every day when you are writing a novel you will never be stuck. That is the most valuable thing I can tell you so try to remember it.”
I always end my day or my week knowing what I need to design next. Sometimes I start shitty first drafts late in the afternoon so I have something to work with the next morning. It can be very tempting, when the work is going well, to “just keep going” and stay at your desk late into the evening. That lovely state of flow is so elusive, we don’t want to walk away—and yet we must.
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.
Fact: everyone struggles to do good work.
Every designer, every developer, every agency or company you admire—they all have good moments and bad moments. Sometimes things go smoothly, but more often than not there are bumps in the road. Confusion. Distractions. Conflicts. Apologies. Second chances.
When things go more good than bad, someone shares what they did and what they learned. A case study goes up on the website, or a blog post or even an article in an online magazine you read.
“How we ninja optimized our responsive unicorn process.”
You sit at your computer, reading the article and feeling inspired. But you also keenly feel the gap between the process they describe and the work you do every day. They’re so talented! you might think. Things never go that smoothly around here, because we kind of suck.
Stop right there; you’ve fallen into the trap of comparing your real, messy, actual work with a story that was created to make everyone in it look good.
Are we liars? Fakes? Scam artists preying on your insecurities?
Not at all.
Talking about our work requires a narrative structure – a Beginning, a Middle, and an End – so that the story makes sense. This was the problem, this is how we solved it, this is what we learned. The end.
But real life does not adhere to a 3-act structure for any of us. We tend to leave out the messy parts – the personality conflicts, the arguments about the technology stack, the 2 months when we were too busy to work on the project – because they muddle the narrative (and make us look less than perfect).
Look closely and you can sometimes spot the chaos in little asides. “Little did we know at the time…” or “We were surprised to discover that…” Translation: we had no idea what we were doing.
The messy parts are always in there somewhere.
And so we aspire to replicate the smooth success we read about, which often translates into an obsession with process. Everyone is searching for the perfect process, because we believe that process is the key to eliminating the messy parts.
Usually, we’re fooling ourselves. A good process can do a lot of great things, but it’s not a silver bullet.
Process is not a substitute for leadership. It is not a substitute for talent or trust or hard work. It will not make up for a lack of institutional support and it will not make hard decisions any easier. I’ve seen healthy teams build great things with very little process, and dysfunctional teams adopt Industry Best Practices and continue to fail. Because unfortunately, process is usually not the cure for what ails you.
No process will ever make real life work as smooth and pain-free as the projects we read about in blog posts and case studies. That world is just an illusion; don’t compare your work to it or beat yourself up for falling short.
Doing great work isn’t about perfecting your process, it’s about maintaining a practice. Every day we try, we fail, we succeed, we learn. Then we wake up and do it again. And again. And again. This is where the real work happens.
A letter to my future self, who will forget these things that seem so obvious right now
“How we spend our days is, of course, how we spend our lives.”
— Annie Dillard
Do more of this stuff
Good Reading: Stop dicking around on your phone at night before bed, and pick up the book you started. You can read a novel for 10 minutes just as easily as you can read Facebook. Trust me, you can. (If you aren’t enjoying the book you’re reading, put it down and pick up another one. It’s okay to stop doing things you don’t like.) You will remember that book for decades; you will forget that Upworthy list by the time you brush your teeth tomorrow morning.
Free Writing: Putting your thoughts into words, every day, is one of the most powerful gifts you can give yourself. You have great hopes and great fears. You have small ideas that might one day grow into something great. You have a list of errands a mile long. Get it all out on paper. Writing puts familiar shapes to the nameless things that live in the void inside your head and makes room for hope and wonder.
Unstructured Time: I know you love making to-do lists, but you will not get lost between the couch cushions if you spend an afternoon staring out a window or idly flipping through a magazine. Remember when you were a teenager, and you’d spend hours lying on your bed listening to the same album over and over again? Nurture yourself. Rotate your spiritual crops. You will burn yourself out if you don’t stop and replenish your inner resources.
Honest conversations: You are not a special snowflake alone in an empty world. Other people are struggling with the same things you struggle with – go talk to them. Listen to their stories. Ask questions. Share what you’ve learned. Rinse, repeat.
Do less of this stuff
Reacting to the day-to-day: There will always be email to reply to. There will always be a doctor’s appointment to reschedule. There will always be a deadline to (almost) miss. This is small stuff. Don’t get tunnel vision on your Inbox or your next deadline. Keep your head up, look ahead, and remember the bigger things you’re trying to accomplish.
Listening to your insecurities: Learn to recognize your inner critic and shut it down. You can’t drown out negative self-talk by stressing out or working harder while it whispers in your ear. You are human – flawed and imperfect. And your work is not you: your work is just work. Acknowledge your fear, and then let it go.
Comparing yourself to other people: When you’re lost in the woods, the first thing you want is a map. Don’t mistake the map for the territory. Other people are not the measure of your worth, and you will never know all the dimensions of their lives – their losses, their failures, their disappointments and compromises – the way you know yours.
Just a little bit less
I’ve gotten a lot of feedback on my work recently, via different channels, and some of it stung. Every bit was fair and well-intentioned, but that didn’t make it any easier to hear that I have plenty of room for improvement.
So two weeks ago I created a new goal for myself: Get better at accepting critical feedback on your work.
I tend to beat myself up over negative feedback and fall into an unproductive shame spiral. Sometimes I get angry; sometimes I get defensive. A weight sits on my chest for a few days while I obsess over what I did or what I might have done differently. Eventually it fades away, leaving behind a vague uneasy feeling like a small bruise. It’s an emotional reaction to what ought to be an opportunity for thoughtfulness, but I’d never considered how it could be different.
Getting critical feedback often feels very isolating. Few people share the feedback they receive; we don’t like to admit that we’re not perfect, either to ourselves or to other people. Greg Hoy wrote an incredibly honest article last year about the feedback he got from his employees at Happy Cog; I look back at it sometimes to remind myself that I’m not the only person falling short of my own measure of success.
I also try to remember something a leadership executive told me about his own experience getting critical reviews and feedback. “I hear the same stuff every time,” he said. “I make the same mistakes over and over again. We all do. Every day I go into the office, and I just try to hold it in the road. I try to fuck up just a little bit less than I did the day before. Sometimes I succeed.”
That’s the dirty little secret of personal growth and improvement: it’s super hard.
We work in an industry obsessed with big wins. Fail fast! Break things! $1 billion acquisition! Ship it! But hacking yourself is a lot more complicated than debugging a piece of code. Changing patterns you’ve had since before you could write your own name doesn’t happen overnight.
For me, getting better at accepting critical feedback begins with having a realistic sense of what’s possible. I have to get used to hearing the same criticisms for awhile, and reminding myself that doesn’t mean I’m a failure. Success doesn’t have to mean annihilating all of my flaws at once; it can simply mean fucking up just a little bit less.
Letting Go of Love
“It is easy to see the beginnings of things, and harder to see the ends.” - Joan Didion
There’s a lot of advice out there about how to nurture your relationship with your significant other; how to communicate, individuate, create deeper intimacy. When things start to get a little stale you can schedule a date night or a weekend away and fall in love all over again across a bottle of champagne. Ah, romance.
But there’s no guidebook for when you fall out of love with your passion project. Your app, your blog, your startup—you gave it endless hours of effort and attention. You alone saw its potential and you poured your heart into it with reckless abandon. Every bit of praise and attention for your work left you walking on clouds like a love-struck teenager.
Until one day, when you realize that your interest has waned. You find yourself daydreaming about new possibilities, and what once seemed so fresh and exciting now feels like a heavy weight sitting on your chest. Is it just another bump in the road, or is this time different? How do you know when it’s time to let go of a great love?
Most of us fall in and out of love with our work – sometimes over the course of years, sometimes in the span of a single day. Like any long-term relationship we go through ups and downs, moments of elation tempered by moments of despair. Usually the good times outweigh the bad, and with care and attention we hope this is a love that will last us a lifetime.
Too often though, we pay attention to the wrong things; we get so caught up in the day to day that we lose track of why we started something in the first place. There’s always one more support request to answer, one more blog post to write, one more email to reply to before bed. It’s so easy to become reactive to the demands of a project, meeting schedules and fulfilling other people’s expectations, until eventually all the fun is gone. The novelty has worn off, and we have stayed too long at the fair.
When we stop being intentional about our work and why we’re doing it then what started out as love becomes just another routine. Thoughtless repetition is fatal to creativity and self-fulfillment; despite our busy schedules, we have to make time to regularly check in with ourselves – to check in with our hearts – and ask Is this still making me happy? And we have to be honest with ourselves about the answer.
Good relationships should give us room to grow as our needs and interests change. Sometimes that means finding new avenues in old projects: unfamiliar things to explore, fresh challenges to tackle.
And sometimes, it means letting go of something we love that we’ve held on to for too long.