A Lesson in Bouncing Back from Web Designer Paul Anthony Webb

“I’ve currently got about 70 domains registered,” Webb says. “When I come up with one I like, I just buy it. I actually started to lose track of them, but I don’t let them expire. You never know when you’ll need it.”

The intensely curious and inventive Boston-based designer’s ongoing projects include building a web browser and operating system and creating his own music for FRSH.fm. It’s not always clear what motivates Webb, except for his deep-seated hunger to experiment and push himself a little farther than he’s gone before.

We sat down with Webb at WeWork South Station, a co-working space in Boston, to learn more about his approach to coding, design, and keeping track of all those domains.

How did you get started in web design?

In 2006, I went to Johnson & Wales for computer science because I wanted to find a way to create my own operating system. But I had to leave because, apparently, I didn’t have any money. That was pretty embarrassing. After I left, I came back to Boston and started doing all these terrible retail jobs until a couple years later my mom was like, “OK, you have to find a way back into school.” She found me an apartment and sent me back to Rhode Island.

Right around the time the economy tanked.

Yup. I was in Cranston, which looks close to Providence on the map but is super far when you don’t have a vehicle. And when the recession happened, nobody could get work—I was constantly applying to jobs I didn’t want so I could pay rent. Thankfully, my landlord was super accommodating and understood what was happening and just kept encouraging me to look for jobs.

But there I was at home, out of work, and bored, so I taught myself Photoshop. I wanted to emulate the designer friends I’d made on DeviantArt, and then I designed a website. I sent it to a shop that converted PSD to HTML and found out it was going to cost $100 to make the conversion. One hundred dollars! I thought, “This can’t be that hard.” So I learned to code out of anger. I watched tutorials with a frown.

When did you turn pro?

I kept working at it and fell in with the Web 2.0 craze. Eventually I applied to thoughtbot’s apprenticeship program and one of the CEOs there asked me to come down for an interview. That’s when he told me my graphic design skills were great—expressive and inventive—but that my web skills sucked. He said they just showed no emotion. And I was like, “Wow, that is truly mean, but truthful.”

And it was his way of saying they’d give me a chance. He invited me to join their program so they could show me how to make my web design better and fuse it with my graphic design capabilities. After that program, I started to get professional work.

How does good design help elevate the products and services companies offer?

First, it just keeps people on the site. If the site looks good, or it’s interesting in some way, people are more likely to spend time enjoying it for its own sake. It also looks more trustworthy. I’m more likely to buy from a site where things look professional than one where it doesn’t look like the company knows what they’re doing on the web.

But good design also tries to stay a little ahead of the curve. It doesn’t take long for things to proliferate. What’s new on the web one day will be on 1,000 sites the next. So good design also helps keep your company distinct because it offers something people haven’t seen before.

In all your experimentation, have you ever had a project that just didn’t turn out the way you hoped?

Absolutely. I created a program called Beachfront to help find and track all of a person’s registered domain names and to pull up things like the expiration date and the registrar. It can be a big mess, so when I got Beachfront to what I thought was a good place, I gave it to some friends to try out.

It completely bombed. I had some real hard conversations where one of my online buddies was like, “Hey, this was a neat idea, but no. This needs to be better.”

I was dejected. But then I came back to it, because I really believed it needed to be a thing. And what I realized was that even I didn’t feel like using my program, because in order to get all the analytical information I was compiling on the back end I had to manually enter the domain name, registration date, price—and I just didn’t want to do all that.

Being honest with myself about the problems motivated me to fix it. I made a lot more of the processes automatic so that it was less painful, and more actually useful and fun. Now I’ve got almost 30 users signed up, and the feedback has been a lot more positive.

So it was your own sense of dread—that feeling “hey, I don’t like this”—that motivated you to make it better?

Exactly. That feeling just told me I didn’t do it right the first time. That’s pretty much always what drives me to go back to old projects and rewrite them from scratch. Marketing automation is one of those things that reduces friction, and that’s key. I don’t want to show my awesome cool thing to people for them to say, “Ugh. Work. I already work enough, I don’t want to do more.” I want people to be excited, and getting there is what spurs me to action.

How to keep going: tips from Paul Anthony Webb

When a project isn’t going well, it can be pretty tempting to call it a day and move on. When it’s a project you really care about, though, it can be hard to say which feels worse—giving up, or pressing forward.

Here’s a little advice from Paul Anthony Webb about what to do when you’re tempted to quit:

• Find someone who will collaborate with you. “Collaboration means you get someone else’s experience,” Webb says. “It can also help you keep a realistic mindset of what’s possible.” A lack of knowledge combined with unrealistic expectations can be a toxic combination during any project. Collaborating with a partner can help you avoid those pitfalls.

• Find value in seeing results. “One thing that motivates me is that I just want to see things happen,” Webb says. “If I have an idea and don’t see anybody else doing it, then I’m going to do it just to see the result.” Even if your project isn’t going the way you hoped, there’s still a lot that can be learned from seeing it through to the end.

• Find a way to simplify. “Stuff takes on a life of its own sometimes,” Webb says. “There’s usually a way to make it simpler. When a project gets too frustrating, I start to look for what I can strip away.” When you feel overwhelmed, take a break and come back with a fresh eye toward how you can make things simpler. It may help breathe new life into your project.