[stakkur]

When it's an entirely new topic, I always build a big picture first: glossary, Key Concepts and How They're Related, What Is Thing For. But that's just how my mind works--have some framework to hang things on.

Then, I tend to follow Feynman's advice: keep trying to explain it to myself until I can make it clear. I typically do this through writing and examples (code, analogy, whatever). I can tell this is working when it's painful, and (for me) it always reveals the parts I don't understand.