To truly go rogue, you need to stop caring what others tell you is important, and start telling others what you think is important. School is where independent thought goes to die, along with financial freedom (unless you're in a program that requires certain certification, such as a medical degree).
Based on all that you've shared over the years, it seems like either something in your behavior makes people reluctant to share guidance/feedback with you, or they share it and you don't remember, or you have the worst luck in the world finding helpful people. Based on your tendency to get sidetracked, my guess is the former. All conjecture of course, with nothing but the words you've written here to go on.
I'd say demand more from those that you are paying to provide a service. They work for you, you don't work for them.
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