"If I Had More Time, I Would Have Written a Shorter Letter" - Blaise Pascal
Naive Simplicity: When you don't know much, it's easy to keep things simple. However, your ideas will have limited applicability and won't reflect reality very well.
Intermediate Complexity: Over time, you can accumulate many semi-connected ideas, creating a sense of breadth and complexity. To get to this stage, you simply have to spend time learning.
Wise Simplicity: Eventually it is possible for the many small ideas you've learned to settle into a larger structure. When that happens, your knowledge achieves both depth and clarity. To get to this stage, you must improve the inter-connectivity of your ideas by continuously updating your older ideas in light of newer learning. These shallow links are what create deep knowledge.
It is important to notice that wisdom comes from the connections, rather than the ideas themselves. Thus, when an expert communicates a big idea, the wisdom that it embodies cannot be passed along with the idea. Instead, the idea becomes just another piece for other people to integrate into their knowledge over time.
It is normal to be wise in only a few narrow areas. However, while we can never be wise about everything, ignorance of things beyond our view will often impact our effectiveness. Therefore, we should continuously aim to broaden our own learning, as well as complementing our knowledge with other people's.
When you are new to a domain it is easy to notice people in the intermediate stage, because of their complicated ways of explaining things. However, when you lack the intermediate knowledge and all you can perceive is another person's simplicity, it's much harder to distinguish between those who exhibit wise vs naive simplicity. In the end, you must be wise to recognise wisdom in others.
To recognise wisdom in ourselves is even harder, as hubris and ignorance will probably lead us to the conclusion that we are wise, more often than not. As Charles Darwin said, "Ignorance more frequently begets confidence than does knowledge". Instead, as long as we keep accumulating new ideas and updating old ones, we can be confident that we are going the right direction.