I definitely have to agree with you that being thoughtful is important. If anything that's what programming is about. Knowing which tools of those available to you are the best for each situation.
On the other hand, he does have a point in the bit you quoted: there's a lot of different considerations one has to deal with, and you're often doing something wrong if your focus is on architecture.
My incomplete answer at this point is to try to always record the scenarios I considered when building, in hopes that it'll keep the code easy to rewrite later on without causing regressions. By taking on that burden I hope to drop the larger burden of worrying about architecture too prematurely.
This is why almost all my thinking lately has been around how to increase the surface area that can be covered by tests: http://akkartik.name/prose (especially http://akkartik.name/post/tracing-tests). Eventually I want us to be able to easily write tests for performance, concurrency, fault tolerance, UI layout, etc., etc.
