I’ve been doing some work recently, trying to re-invent the index page of a really large project that I’ve been attached to for almost a year now. It’s a homepage for a community portal site that is produced by an “old media” company, a newspaper specifically. As I’ve submitted countless designs for every imaginable user interface element and page layout, I was reluctant to start again; our company in internally famous for epic and glacial “feedback loops”, and I was in no hurry to find myself defending every last inch of my work to people who may or may not have any idea why it’s important—given their somewhat ironic position of web people trapped inside a newspaper.

After a recent submission, I received a well worded and polite response. It essentially said that we were very close to having a finished candidate, but some tweaks to color would be necessary to move on. I’m fine with this, at least publicly. Internally, however, it makes me want to scream. Even though the writer is a seasoned veteran of the newspaper industry with an above average grasp of the internet as a communications medium, it still makes me cringe. As a company we’ve been tasked with growing virtually every metric we have to measure ourselves by an abstract percentage. That number is in turn based on something only a newspaper would have the sense of humor to map its success against: the penetration and market size of the average locally owned TV station—the other dying medium, besides making records to sell. Management hasn’t been given any terribly clear direction about how this might be accomplished, but many of them seem to think more display ads will do the trick. This is what I hear approximately half the time: grow business, design with ad space in mind, make it conservative. The other half of the time I hear make it ‘web 2.0’, we need ajax, we want comments and tags on everything.

Someone is lying, or wrong, or both.

So when I get feedback on a design whose brief was “bleeding edge, ajax, show-and-hide” that says “these colors are too bright” I feel as though I’ve landed on the ape planet, and there’s a giant Photoshop toolbar jutting out of the surf at right angles. But I’ve realized now that it’s just because we’re trying to do two things at once. We somehow need to keep the average 54 year old female reader—who revolts and calls us on the phone when we move the sudoku puzzle—and convince the 18 year old that we are just as cool as Digg. I’m growing increasingly dubious as to whether this can be done.

I think these dual goals are fairly common in businesses like newspapers, where it’s increasingly obvious that current technology has rendered the stuff we were once good at pointless; there’s a feeling of wanting to hold on firmly to the vine in hand while you look for the next one, even though everyone is telling you it won’t hold you and your baggage. Another example is the frenzy to extend support for IE 6. The fear of making customers unhappy by not supporting their nine year old software—or losing them altogether without more to replace them—is palpable. This fear pushes companies into announcing, with all seriousness, an intention to post positive growth simultaneously along every measurement it has for itself. It makes them spend time and effort figuring out custom newspapers that only cover your specific eighteen block neighborhood. It makes them hate Craig Newmark. It makes them announce they are competing with Google.

When we set out to redesign this site almost a year ago our team did everything it possibly could to distance ourselves from newspapers. We chose a software back-end that, up until that time, had been largely untested for that specific purpose; we designed with wild, complimentary colors and urbane type faces; we envisioned a site where almost everything was user-centric, where you never saw anything that you didn’t ask for. In the process that ensued, whittling away became incising. What is left bears enough resemblance to be recognizable to us, but I’m not sure it’s what we promised our users. We’re a different group now, and even though current events keep some of us trapped in meetings for hours at a time there are still good ideas circulating here. Newspapers want you to believe that being successful in 2008 would require them to see into the future. This is a lie. It would merely require them to see into last week. The pieces are all here, and there are thousands of people who want to do the work. It’s just that for every one of them there’s a counterpart, working hard to make sure we keep serving two masters.

I don’t know, maybe he just hates green. (And he really is a nice guy. Shame about the green, though.)