Humans are a differentiation machine, they follow along known branches until they break into something new. There they can create a new branch where they might be first or one of a few new minds in that area, in that case, 'winging it' may be employed but it is also based on experience in what to do with unknowns.
With any production/consumer scenario it is usually 1 to 1000 or more ratio. Most people aren't making new territory all the time, even inventors or creators. The fact is most of human existence is observing, studying, thinking, following, viewing existing knowledge while very few interact or create new production or are producing at one time on one subject or concentration, we are usually part of the 1000, though we all are the 1s for something.
All of that preparation prepares you for the moment where you meet new ground that must be entered and conquered. So new areas, even for the most experienced, are essentially 'winging it' uncharted territory until it becomes a solid branch of growth in the individual or industry/area of expertise. It is a bit like practice, which is a series of sketches until the time you have to use that skill in production where the refined lines, inking and color are put together, the art of progression/innovation comes together for production.
Then comes the 'here we go' and 'let's do this' moment where even experienced and skilled professionals take flight with the butterflies in their stomach of nervousness and excitement to conquer unknowns in uncharted territory with their pack of experience and knowledge, the experience/book smarts meet the reality/street, the adventure begins.