I personally find that doing it well in the first pass slows me down and also ends up in worse overall designs.

But I am also pretty disciplined on the 2nd pass in correcting all of the hacks and rewriting everything that should be rewritten.

There are two problems I have with trying to do it right the first time:

- It's hard to know the intricacies of the requirements upfront without actually implementing the thing, which results in designing an architecture with imperfect knowledge

- It's easy to get stuck in analysis paralysis

FWIW I am a huge fan of John Ousterhout. It may be my all time favorite book on software design.