Excellent post!

For instance, before looking at a single example of calculus, Simon might have written down a list of idea areas to explore: "jobs, personal life, the natural world, engineering, other". He would then take the first broad category, "jobs" and expand it into a longer list, perhaps "agriculture, teaching, customer service, manufacturing, research, IT, other". With this longer list, he can then focus on each area in turn and either expand it further if it seems especially rife with examples, or come up with an example from the area directly.

I am going to start searching for any opportunity I can find to use this method, because I'm really curious to see how well it works.