It's easy to spot the tourists in New York City, just notice the people constantly looking around, either in awe or pure confusion. They also usually have maps and are trying their best to navigate where they are going.
You can study a map, read articles, talk to the 'locals,' watch videos, etc. but to a certain extent, when you are visiting a new place you will still feel (at times) a little lost and unprepared. Something always comes up that causes a moment of panic.
This happens when we are trying something new or doing something for the first time. We will always feel unprepared.
We've been trained to not be okay with this. We, unfortunately, compare this feeling of unpreparedness to how we felt when we took a quiz in school and forgot everything we had previously memorized.
This feeling of being unprepared is not a happy feeling. So we might be tempted to take certain measures to ensure we limit the number of times we feel unprepared. But therein lies the paradox. The things we feel most unprepared for are the very things we should embrace and pursue. For they are things that bring the most satisfaction. They will be the sources of our growth and development.
Another thing about the 'feeling' of being unprepared. There comes a point when this feeling is a choice. You may still be leaping into the unknown, but you've seen it play out enough times that you have an idea of how it possibly ends. I'm convinced that this ability to remain confident in ambiguity is one of the most important skills someone can develop—especially when it comes to navigating one's career and, of course, life.