I don't claim to have ever achieved perfection with anything I've done. But I can say from experience of designing a lot of systems, that the initial designs are usually messy and complicated. A lot of developers stop there and start building. But if you keep going, at a certain point things start to become simple and obvious. That's how I know I've managed to get to the core of some certain problem. It's a great feeling when all of a sudden the design or approach seems to just fit perfectly.

I don't really know how to get there except to just continue re-working things until that magic moment happens.