While you're 100% right, the key word to me here is "hierarchical organization" - and I remember my history teacher, the best I've ever had. She was demanding,

While you're 100% right, the key word to me here is "hierarchical organization" - and I remember my history teacher, the best I've ever had. She was demanding, on fire all the time - and most of other students and teachers hated her, but she was just extremely passionate and uncompromising, teaching from first principles (I've never learned as much from a teacher while in school). This tends to set mediocre people off, and she got really bitter in the end. All the skills OP is showing make him a bad fit for large places full of B and C people (i.e. all of academia and corporations) - while his healthy self-esteem, passion, a learning and teaching spirit, great writing, aspiration and the drive for simplicity and good UX (like in his courses) make him a perfect fit as a founder or early startup employee. He should be prepared to fight an uphill battle if he tries to stay in academia full time. If I were him, I'd try to do an industry career first before returning to teaching, I'm going down that route as well. Even my all-time hero of academia Feynman helped build the atomic bomb before returning to teaching first semesters.