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Going into our 3rd year, I am amazed at the number of interface challenges Wufoo’s created for me. So far I’ve created over 50 interfaces and designs for our little web app and it feels like a portfolio in and of itself. I never really thought about how exciting creating a tool could be in college—where assignments had definitive beginnings, middles and ends. It’s always weird to think about how my great plan in life before getting into the startup life was to teach digital art to hippies. I may still go into teaching some day (I do love to share), but I think I’ll probably be a very different teacher now that I have some “real world” experience under my belt. The start of a new year is usually a good time for reflection and so I thought I’d take some time to write out some surprises and lessons that’s shaped me so far as a designer.

Web application design is surprisingly organic. I’ve never designed something so volatile and delicate. In college, web design always felt cold and distant. It was the least exciting medium for me. I preferred anything else to it: print, paint, sculpture, mixed media, video, performance. I was addicted to eliciting emotions and I couldn’t imagine anything farther from my audience than the Internet. But Wufoo has showed me that software can have personality and feel more alive than anything else I’ve ever created. Because thousands of users are using something I’ve created in realtime, it responds almost immediately to the slightest modifications. Moving a button, changing a color, rewriting copy. All of it matters and in different and surprising ways. This is so different from creating framed art work for a gallery where feedback and the possibility of response and interaction is difficult and mostly non-existent.

On a web application, the design breathes and exhales through customer support. I’m so glad we have Chris on our team. He’s our customer evangelist. Through him, I’ve come to believe that there’s nothing more important than to monitor and man those incoming emails and respond as quickly as possible to every single inquiry, request and comment. It’s the pulse of not only the application, but the business as well. It’s in support requests that Wufoo lets us know when something isn’t working. It’s there that she lets me know when I’ve done something right.

And I can’t talk about Chris without talking about his brother. Here’s what I’ve learned from Ryan: If you want remarkable results, feed a good programmer a diet of good design. It’s like Wheaties for them.

The only piece of wisdom I’ve learned while working on Wufoo concerns what separates good designers from bad designers. For most designers, the relationships they care about most is the one they have with the design. They seem to only love the design and more often than not, they tend to love the design too much. These designers focus on their legacy at the expense of the audience. The user can suck it. You can hear it in the way they talk about the design and how they talk about their users. They’re arrogant and defensive.

Good designers, however, are more like matchmakers. They design for the relationships between the tool and the user. If you know anything about relationships, then you know that this is extremely difficult. To be good at relationships you have to not only be selfless, but listening…constantly and carefully. When I started working on Wufoo, I was definitely a bad designer. I thought I was hot shit and knew all the answers. I saw the user as a wild beast that needed to be tamed. He got in MY way. Use the tool the way I designed it, fool—not the way you think it should work. Thinking back, I remember being angry all of the time.

I think all I really had going for me then was a nice aesthetic and the ability to look at something in a surprising light. After awhile, I’ve slowly come to see that successful designs augment a good head start with constant iteration and deep observation. Designers, on their own, can only get you 1/3 of the way there. Your users and your ability to adapt helps you create the rest.