Thought I will contribute some, starting chronologically and moving up to my present self.
For middle school I was in a school where we had "steps" not grades or courses, one could finish all the work needed for the whole next 4 years in the first year. This went for the subjects English, Swedish and Math.
I convinced the teachers I was really good at math and got to skip all of it, I wouldn't really classify this as a shortcut since the skipping part had merit (I would have done the math fast anyways). But maintaining a close relationship to your teachers lets you get away with a lot of things.
In highschool and college I faked dyslexia in order to get more time in standardized test. In highschool this didn't really help much but in college math it did since many of the question had brute-force answers which could only be found if you had enough time. Much of my work was also proofread and plagiarized from other students.
I'll go into my job interviews and professional life later if this thread sparks some interest.