After reading "A Tale of Two Architects" by David Armano (Logic + Emotion), I found myself thinking more and more about it in relation to web design. With two opposing ways of reacting to how people interact with your designs, I'd like to think I'm more "Jane" than "Dick" in that regard. With Dick, it's all about control, his design - his vision of how it should work, and his discomfort in people interpreting his work in ways it wasn't meant to be interpreted. Jane, on the other hand, is more tolerant to re-interpretation and sees it as a learning opportunity and notes it as something to incorporate into future designs (yay Jane!). Who do you think will be more instrumental in evolving design - Dick or Jane?
It kind of reminds me of how you'll often come across an institutional campus where the building layout, green spaces and pathways were all planned by the designer. Invariably, you'll find dirt trails through the grass where people's preferred routes take them between buildings. I wonder what it would look like if the designer left the pathways unpaved for a year letting people carve their own trails through the green and then paved the strongest people trails.
Back to Dick and Jane, is it not important to continually seek out new, different, better? I think it is. The web as a medium is constantly evolving and I believe we need to be more "Jane" than "Dick" in this regard. Be open to new interpretations. Watch your users and learn from them. Don't be afraid to let them carve out some of their own trails.