How to Ignore Your Emotions (while also thinking you're awesome at emotions)
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"What are all of the intuitions I have about what is involved in letting someone else grow on their own terms and letting them get into trouble to learn from it?"
This made me think of something I tried, and I think succeeded at, a few years ago. There was a part of me (call it Subagent A) that was pretty convinced that I was somehow inherently bad at the domain of study I had chosen for myself, and was pointing at my bad grades in that domain as evidence. The rest of my mind thought I was bad at a large number of things for other reasons and pointed to the fact that my grades were bad in nearly all domains that required any significant amount of effort.
The rest of my mind was unable to talk Subagent A into changing its belief, so I thought that if I fed myself some new experiences where I was doing really well in this domain, I could shift that belief. (I know my phrasing makes it sound like this strategy was simple to arrive at, but I actually spent a long time trying other things before I tried this.)
To this end, I spent a few semesters taking a very small number of genuinely demanding courses in my chosen domain, got very good grades (and positive recognition from the people around me), and became much less concerned that I was inherently inept in this domain. (It was lot of time to invest though.)