One teacher once found personal gratification by grilling me for 1 hour in front of the class room: He set up an advanced math problem 4 years my senior and ridiculed me until I started to cry. "See, even you don't know everything". This happened when I was 11 years old. Yay for education professionals!
Now, as you said, there is always going to be a wall ahead. My parents have no college background so I was pretty much left alone after I finished high school. I enrolled with the Swiss Federal Institute of Technology in Computer Science and bombed HARD. I was shy, I didn't know how to make friends, I failed at simnple administrative tasks required when growing up, couldn't support myself financially and on top of that the course material obviously wasn't going to be a walk in the park.
To this day I struggle with "boring" work and procrastination.