There's a lovely bit in Egan's Diaspora showing the viewpoint character understanding a concept from physics by applying it in various contexts.
More generally, I don't know if much is known about how people get from input to understanding.
Possibly of interest: Mathsemantics, which grew out of a project to find employees who understood what numbers mean. The book (about a questionaire for the purpose) is very interesting, the articles listed mostly look minor except for the one about grokduelling (you win if you understand the other side better), and they're looking for research ideas.
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Part of why the future looks absurd is that people want novelty--not absolute novelty and not all the time, but a lot of smart and weird people are working on making changes, some of which will catch on. A futurist isn't going to be smart and weird enough to predict all the possible changes being offered or which ones will have a long term effect.
It's not just that technological change builds on itself, so does social change. I don't think it was completely obvious that the civil rights movement would contribute to gay marriage becoming a serious political issue.
No matter how hard you try, you are of your time. You can expand the range of your imagination, but the future outnumbers you.
I'm still working on the question of why the future isn't just unpredictable, it's absurd. Maybe there's something about human cultures which requires limiting both what people do and what people can imagine *anyone* doing to a small part of the range of possibilities.