A good starting point would be to have people brainstorm examples of things that they had been exposed to but did not and could not understand at first, but which clicked together after they saw something else.
When I mentally map useful concepts talked about round these parts, they fall naturally into philosophy, metacognition, and a "practical" category composed of habits, skills, and knowledge. However, to the extent that concepts benefit from being known in order, they don't usually have more than 1 or 2 levels. I guess philosophy comes closest to having a "tree" of sorts.
For example, look at this. It is very appealing to the intuition. It sets up a progression of insight which is sort of valid, maybe...but...does the 1-2 emotional transition really preclude realizations 3 and 4? Does Realization 3 actually help with Step 2 behavior as claimed? Are there not people who convincingly proclaim step 4 while not really getting step 3? Maybe these are actually 3 entirely separate things?
It's not trivial to know how things are related.
A while back I came across a delightful web developer skill tree, and I was wondering if technical rationality has gotten to the point where someone could make one of these for an aspiring rationalist.
I think seeing a clear progression from beginning skills to advanced ones laid out graphically helps those starting on the path conceptualize the process.