Really good piece Jess. Plenty to mentally chew on here.
For me, adaptability is the key. As writers, educators (at any level), parents - and many other roles in life - we need to be able to write for the people we hope to be reading our work.
It's not good being the middle school teacher who talks to his students using a standard of language more appropriate for conversing with Phd candidates; but neither is it going to be helpful for a high school teachers to talk to her class of sixteen and seventeen year olds as though they are kinder-gardeners.
I consider someone who doesn't 'personalise' their speech for the specific person/group of people they are talking to (most likely) unworthy of my time and attention.
As another example, a doctor who uses language too complex for their patient to understand - yet also, on the other end of the scale, a doctor who addresses every one of his patients with the vocabulary common to small children.
What this adaptability requires, is obviously Emotional Intelligence, for writers (speakers/listeners) - to be able to vary your approach to suit the individual or group, rather than treating humanity as a homogenous mass with a common intelligence and consciousness.
Reading and learning should also be tailored to fit the unique needs of each of us (I really should write an essay about schools....be warned it will be a long one, lol) - and yes, we should always be willing to stretch and challenge ourselves, be curious, continue to feed and expand our minds throughout our entire lives.
However I realise that I'm 'preaching to the choir' here!
Perhaps it would suffice to say, I understand you, I'm with you and as ever, I applaud you. Thank you for sharing your thoughts.