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From Nietzsche (found in Dwell Magazine March 2005)

When one has finished building one's house, one suddenly realizes that in the process one has learned something that one really needed to know in the worst way -- before one began

This quote was really heartening as it applies to architecture and construction, which are far older than web design or any of the elements that are components of getting to that end. A relatively young profession, such as web design or even digital design or software development hits this exact spot in nearly every project. This could be why we love the iterative process and capturing and building upon lessons learned. We also read incessantly about everybody else's endeavors so we can learn before we design and then build.

Jason Fried posted Getting Real, Step 1: No Functional Spec, which makes a lot of sense in this iterative design perspective. I have done a few projects (not in a few years) that worked in this direction and we got into a prototype rather quickly, which we learned from as we went a long. We built things in a modular method, so that we could throw out small pieces or everything (we never had to throw it all out).