Responding to Silas's comment about the learning side of the equation. He wrote:

Don't forget the problem from the other side, too: how to detect and bridge inferential distence for knowledge-havers, i.e., how to find the knowledge-gap and convey the information to them. (That was actually the long-delayed article I'm working on, given my success in teaching others and my difficulty in getting others to convey knowledge to me when the roles are reversed.)

(The use of the term "knowledge haver" rather than "teacher" was deliberate.)

Yes, I used the activity oriented "learner" over the institutional role of "student" specifically because I was trying to emphasize general life skills.

I think it says something about our culture that there doesn't appear to be a common term to describe "one who conveys a lesson" but that doesn't have the connotations of "teacher" in that it is something people do for money. When I suggested an article for "teachers" I used the best non-neologism I could think of. Having thought about this some more I'm wondering if I "mentor" might be a better term than "teacher"?

The trick with mentoring is that its a long term process and is less about delivery of pre-specified lessons and more about delivering supplementary insight into the mentee's ongoing currently articulated life processes.

Thinking about the terminological issues, it strikes me that these conceptual framing issues have implications for what kinds of learning/teaching are actually possible. Perhaps a lot of the skills here involve having a realistic model of a normal person's willingness and capacity to learn? Maybe you just can't teach/mentor/tutor very well without long term insight and life-driven discovery of knowledge gaps? Maybe other languages cut the world in better ways? For example there's senpai and kohai in Japanese, but that also carries baggage about organizational status hierarchies rather than transmission of specialist expertise itself.