What does his job entail really? Seems like it would be a lot of handshakes and the occasional “hard no” on penetration in the cartoon movies. What else am I missing? Disney is a national treasure and doesn’t rely on one guy to run it. These bloated positions need to go when you’re not a start-up.

To me this sounds condescending and doesn't really help much. Who doesn't want to have control/influence over how their life will be 10 years from now - even if you're in a rut? The difference between settling and choosing is a fine line and worrying about future regret isn't the answer. Do your best and don't beat yourself up for your choices - just grow and move on.