I think your question is legit. It shouldn't be down voted. It doesn't apply to science and engineering disciplines because we humans have made those disciplines "human proof" by rigorous analysis and testing. Here when people say "winging it" is I think meant to point out that Humans are limited in their capacity to know everything about things ,especially predict the future yet people sometime act like they do know. "Winging" might be a coping mechanism we have to employ to stay relevant in the rapidly changing world. It may not have been true 100 years ago.