Complex apps “do more.” But they do it at the expense of crashes, and a manual in seven languages. Users use them, they hate them. They’re trapped by some function that no other app has, but that they need.

Take Photoshop for example (please take it!). No other app does RGB/CMYK, and compositing as elegantly. It’s amazing with it’s bezier curve handling and it’s simple yet incredibly powerful layer management. But on awkwardly grafted on top of that are functions like 3D compositing, check-in/check-out, and “share my screen” which nobody uses. These three examples are some of the more egregious, but they’re nowhere near the totality of the list. The whole app is a cruft of duplicative menus, bad help systems, and wanderingly bad UI.

But I still use it. Why? Because those features I need very badly to be good at my job are found nowhere else within a single app. If they were, I would pay not only the (freaking) $700 I normally pay for a license, but I swear on my design career I would pay double. Double.

I would pay double for an app that did the things I need in Photoshop, but did not crash, and did not suck. I want prettiness in a UI. I want logic, and elegance. Like most designers, I love surrounding myself with well-built things. I find joy in interacting with a laptop hinge that slides into place just-so, or a touch screen that actually reacts to my touch.

There are apps like http://www.pixelmator.com/ that I’m dying to use. Gorgeous, well planned, and humanist. But it doesn’t do the things that I absolutely have to have to make the switch. The pain of switching would mean I have to run multiple apps, or keep a copy of CrashyShop on hand for use many times a week. It’s not worth the pain. No matter how much I love beautifully designed things, I have to make a living with my tools, and if anything slows me down even slightly, I’m not going to use it.

So. We have about a million blog articles online today expounding the excellence, and instant success of “simple.” You can even look at our blog to see how we’re devotees of “less.” But I’ll be honest- our most profitable app is our most complex. People pay for functionality if it is done well. People use simple if it is free…

So as developers we’re left with a problem. Feature-rich applications lead to crufty interfaces. It’s not unavoidable, but it’s nearly inevitable. If you’re ever going to launch your app you must (MUST) limit its feature set. But if you’re ever going to make money off your app, you have to keep adding to it.

Gradually, like the ocean tides, you wear down the apprehension of your audience. Keep beating the drum. Keep enticing people who have tried it once before to try once again. Eventually the feature that kept them from sticking before will be the one you just added. But the game is to do it well. To do it smartly. To add features without adding complexity.

We are not experts on the subject, but we’re cracking every book, blog, and beer we can to try to get to the bottom of it. Every new feature brings the chance to add new users, and alienate old ones… It’s the way you add it that makes the difference between winning or losing users.

In Dee Teal’s case, she didn’t always know she wanted to build websites for a living.

Dee is a freelance web developer. In a previous lifetime, she worked as a personal assistant for a non-profit organization. Part of her role there included updating the website- and she took to it “like a duck to water.” However, the other aspects of her job didn’t excite her quite the same way. She took the first opportunity to head to the IT department, where she took care of all eight websites her non-profit owned, and hasn’t looked back since. Today, she freelances, and works with designers and project managers on the back end of websites. She took a few minutes to answer some of my questions.

A bit about the process.

“The first step for me is to get a map of the navigation and site structure. It helps me have a clear idea of where we’re going- I find if I can get a handle on the structure the design will lay over the top… actually design is always the last thing I look at… So when the project manager and I have the structure down then the design kicks in… (usually. It pays to be flexible…) This is where Jumpchart has been really useful to get things mapped out BEFORE we actually start the build.”

I appreciate Dee’s perspective here, because it shows having the navigation and content laid out first is not only useful for designers, but for programmers as well. Whether you’re on a one-man-team, or collaborating with others, it helps to get that part nailed down.

So what other tools does Dee use in her process?

“As far as tools are concerned I ‘m a Mac user on an MBP15in and the software I primarily use is Dreamweaver/Photoshop and Fireworks all part of the Adobe Creative Suite 4. I also use Firefox with the Web Developer Toolbar and TextWrangler/Cyberduck FTP for editing static HTML on the fly. Oh, and Jumpchart too, of course!”

Some advice.

“The biggest, best advice I ever got is to Listen. The more you listen, not just to the text but the subtext of what clients want, however crazy it may seem, the better prepared you are to be able to give them what the didn’t know they wanted… We’ve all had those clients who appear to want the world, flashing gifs included, and it’s SO tempting to shoot them down and tell them what’s best… but if you REALLY hear them, in that they really want their logo to be the thing that people remember, then you can show them how it’s done WITHOUT the flashing gif… and then everyone goes away happy…

“The other thing I think is really important is to always bear the user of the site in mind – not just the client- I do my best to educate, in the nicest possible way, the client into thinking in terms of the users rather than just in what the client wants to say with their site… Basically, if everyone’s thinking about who they’re serving (client, their public, designer/developer, their client), challenging though that can be sometimes, then, in my mind, everyone wins.”

Dee’s proof that your process needs to be flexible, but that no matter what your role in building the site or app is, it pays to get organized first.

See her work here.

I know how weird that sounds. But consider for a moment. We are human beings; our first responses to anything are dominated not by calculations but by feelings.”