To outline or not to outline...?

Consider this a combination writing-process-post and request for help.  There's always a debate about whether it's better to plunge right into writing a new draft or to craft a meticulous outline first.  I know of hugely successful authors who do both, and I think a lot of it comes down to what works for the individual writer.  But what if you're a plunger...working on a project that wants an outline?

I've never really been an outline person.  More often than not, I start a new book with a bare-b