It would have taken Dann Petty a lot to quit freelancing. And it did. When the 30-year-old designer got a direct Twitter message from Ev Williams, it was a foregone conclusion that Petty would go to work for Obvious Corporation—the company behind Medium and Jelly—and set out to design one of the web's most gawked-at content sites.
"Going to Medium, the team didn’t know what it was going to be but we knew whatever we created, it had to be different, and a step forward," recalls Petty.
Though the site’s writing interface has been lauded since then, it was still a new kind of design pattern at the time, and new things on the web are too often excoriated.
"I think all of us designers have created bold designs like this for our clients at some point, but it’s a risky type of interface," because of its newness, says Petty. "We always get push back on those type of things. It was great to see Medium embrace it."
Petty left Medium in late 2012 to work on his own project called Hum, pictured above, a messaging app looking to redefine the inbox. The app is nearing release—there's a waitlist available now—so we figured this was a good time to ask Petty to look back on his days with Ev (and before) and tell us what he learned.
"I went into the job at Medium thinking Ev knew everything due to his background, but I was super humbled by how many times he says ‘I don’t know, but let’s figure it out,’" says Petty. "In design, I use to think I had all the answers because of my quick upbringing, but after working with Ev I quickly realized I was doing it wrong."
Petty says the trick is to treat each design challenge as a potential exception to the rule. "The major thing I learned working with Ev is that there is no secret formula to all of this. You read articles everywhere online about strict formulas you should follow about coming up with ideas or proper launches. What I learned is that there’s no one secret answer other than plain old hard work and focus."
The trouble with plain old hard work? It takes a lot of motivation.
"I remember Ev walking into the office one morning at Medium and putting up a 200-hour shot clock, out of nowhere, for launch. That’s not something you read online or in the ‘startup’ rule book. That shot clock helped motivate us to be more focused on the puzzle pieces we could actually build quickly and launch with," says Petty. "We worked on some crazy things, building some cool stuff really fast, but ultimately we decided to cut some of it short and just launch."
I asked Petty what else he learned at Medium, and at his prior jobs—as a junior designer at Fluid in San Francisco, and then the advertising agency BSSP in Sausalito—where he did work for clients like The North Face, Mini Cooper, Priceline, EA Sports, LucasArts, and Converse.
If you freelance online at all, you’ll see vicious arguments over whether or not you should work for free. It’s a dividing issue which has valid points on both sides, but Petty clearly comes down on the side of working as much as you can, whether that’s for free or pay.
Part of that, Petty says, comes from his time working at BSSP in advertising and learning the value of pitch work. He details one story wherein he was only supposed to make minor changes to a website, and ended up re-doing the entire thing out of pure ambition to do good work.
"I use to get in trouble for putting in extra hours to make the work better," he says. "One time I was tasked with making some 'small' changes in about four hours to a website we were creating for Mini Cooper. The site was terrible, though, and I was not motivated one bit to work on it, even if it was Mini Cooper. I didn’t care. But what I did care about was making awesome stuff, so I completely redesigned not only the entire site, but the entire site concept on my free time after I made the small changes. The next Monday I presented it to Mini and blew their minds. It went from a decent project to an award-winning site over the weekend."
That’s kind of Petty’s philosophy when it comes to design, do what’s right. It’s also usually how he arrives at the finished project in the quickest way. Talking about his workflow and preparing for jobs, he says it isn’t about planning for him, but about just starting.
"Planning takes time, I look at design as wanting to get to the solution as fast as possible."
Petty isn’t against sketching out an idea, wire framing, and planning, but that type of stuff isn’t what he subscribes to. He’s very much in favor of getting into Photoshop as quick as possible and making, what he calls, "Happy mistakes."
Anyone creating content is constantly looking for that "aha!" moment—when the project comes alive and makes sense. For Petty, that doesn’t come from gathering screen shots of other people’s work or making everything work on paper. It comes from trying things that might not work, mistake after mistake until the mistakes line up and everything fits.
"I’m a believer that almost every single successful project or new innovation was made because of a ‘Happy mistake,’" says Petty. "That’s the beauty of designing on a computer, it’s so easy to tweak and tweak and tweak until you accidentally paste something or turn off a layer style, and Eureka!"
Sites like Dribbble, Behance, and others might be fine for some designers, but Petty’s advice of looking within for your own ideas is much simpler. That’s why if inspiration is lacking for Petty, he’ll go surfing or head to Tahoe for snowboarding, usually just something outside. "Design inspiration comes from life, not a desk," he says.
Asked who Petty sees as a great up and coming designer, he says: Jared Erondu.
"Erondu’s like 19 and just ripping it. He’s awesome because he’s starting out in a super trendy design world, but already has his own style which he’s focusing on. You see these other guys starting out who are just trying to catch up to the latest trends since it’s ‘hot’ but once those fade, they’ll fade off with it."
After working in his industry for the past 12 years, Petty says he pays attention to entrepreneur mentality—what prompts people to redesign a site for free over the weekend just for the sake of improving it. Those are the types of people you want on your team, and that's what something Petty sees in Erondu: a passionate designer rather than a paycheck designer.
Often jobs at Twitter, Facebook, and Google are thought of as the end destination, the goal young designers and developers are trying to reach. The companies which started as small startups pushing the boundaries, however, themselves often can be graveyards for creativity and bold work now.
"I think it’s important for all designers to freelance, even if it’s on the side of a full-time job, just to get more exposure to different ways of thinking and design styles," he says.