I enjoy hearing people talk passionately about very specific work they do: the designer who drew Cursor's icons
What I'm looking for is what I think of as the attractor: the soul of the object, the shape a concept keeps pulling toward. What makes a bin a bin? At what point does a question mark stop reading as a question mark? Inside that attractor there are still plenty of ways to draw the thing, but it has to land instantly. It's communication first. When the industry hasn't settled on something, there's no attractor yet, so it comes down to exploration. You try the literal version, the abstract version, and everything in between, and you put them next to each other until a few start looking better than the rest, then a couple better than those, until you choose one.