If you're going to teach the Enneagram or something like that, you need to be able to put the narrative of the human condition into your own words. You learn how to do that with your own self-observation practice, obviously, because the more time you spend on it, the more you see how you're going through what everyone else is going through. You obviously are going to have your meditation practice as your right-hand man. But you also learn from listening to others do it. Sandra Maitri is a master at it, other Enneagram teachers are a master at it, and so is this guy, Jacob Needleman. I once read in The Great Work of Your Life, if you want to speak or write like the masters, listen to their words and re-write them. Write them out over and over, or listen to their talks over and over, and the more you get their throughtstreams in your own head, the more they open up your own unique way of explaining things.
Right now I'm digesting a video I've been watching the past couple days- it's an almost two-hour interview between Michael Lerner of Commonweal's New School and philosopher, professor, and author, Jacob Needleman. If you have two hours this week, or if you can carve two hours out, I highly recommend spending this time with Needleman. My respect for his intellect and personal practice grows more and more as I hear him speak. He's been a student of George Gurdjieff since just after graduating from his master's at Yale, and he's just got a beautiful soul now that he's in his 80's. A SP/SX Type Eight soul if you ask me.
They bookend the talk with two meditation times wherein his wife (I'm assuming- her last name is Needleman) plays some Gurdjieff tunes on the piano. Beautiful for meditation. And then at the end, he says if you want to study this further, get together with some philosophical friends and read some books about Gurdjieff. I'm interested in starting something. Like where three or four of us get together and read a book and discuss it. I'd have to buy a couch if this happened, so people had somewhere to sit... but if you're a philosophical friend and enjoyed this talk, and you live in Regina, message me.