Well written post, and good to read about your experience.
I had some similar experiences (bored in high school, able to keep straight A's with little actual effort, but always anxious about grades and how they tied into my identity). In college (Electrical Engineering and Computer Engineering), I had a much better time (many intellectual friends), and kept up my good grades.
Then, I took a semester + summer off to do an internship, and found out how little being "smart" in school relates to being "smart" in the "real world." That broke me, at least temporarily.
After returning, I was back to being bored. I started reading more for pleasure and helping friends study their subjects, in an effort to build general knowledge to combat this, but in my own classes I couldn't bring myself to put in much effort.
Eventually I hit upon playing a dangerous game. I knew I had a psychological compulsion to be someone who got good grades, so I slacked in doing assignments and tests until I had only a slight margin for error. In Linear Algebra, after the first test, I had 6 points to lose the rest of the semester to still get an A. Similar story in a few other classes.
The dangerous game worked in that it motivated me to pay attention to my classes. Sometime in the next semester everything clicked again, and I was able to take interest in academia for the sake of academia. I wound up thoroughly enjoying the rest of my classes (and graduated with a 4.0).
I never articulated my strategy to myself (handicap yourself so the task is more interesting), but I kind of knew what I was doing in the back of my mind. Even though it worked, it could have just as easily backfired. My professors could have shrugged and stopped taking an interest in me, and if I'd done poorly in classes I might not have rekindled the flame, so to speak.
In short, I think it is rational to be careful with what experiences you expose yourself to if you suspect they might undermine your motivation.
I actually used a similar strategy for rather different ends. In my undergraduate work, I would routinely write the first paper of the class so that I would have graded it a "D" or worse. Then I would use that as a reference for how hard I'd have to work in the class.
Sadly, there was a class or two where I got A's on those.
I lost the Way, even when I didn't know what I was trying to follow, when I learned a Dangerous Truth about school. This is a brief recounting of how I lost the Way, came back, and what I believe we can learn from this. I hope you find it instructive.
I suffered from insomnia as a child. Not because of any traumatic events or abuse (if anything I had an exceptionally comfortable childhood), but because I would lay awake in bed, staring into the darkness and worrying about school. I worried that I wouldn't complete assignments, that I would fail in subjects, and that terrible things would happen if I didn't make straight As. None of my fears were well founded, though: I was never at any serious risk of failing to complete an assignment, getting anything worse than a B for a quarter grade in a subject, or having indeterminate terrible things happen to me. I experienced this anxiety in part because I was suffering from undiagnosed obsessive-compulsive disorder and in part because I believed that the most important thing in life was to succeed in school. If school was a game, I was playing to win.
I continued in this mode all the way until I entered high school (9th grade in Florida, USA). Since it's not significant to this post I'll omit most of the details, but the short story is that I did not enjoy high school for a multitude of reasons, not least of which was that I felt held back by teachers and administrators who didn't want me advancing my learning too far past the level they were trying to teach.1 I don't think most of them were being malicious, but had their hands forced by an educational system that is more concerned with average performance and improving the results of underperforming students than allowing exceptional students to succeed. Looking back, if I'd had more guts I would have pushed to take my GED and gone to early college, but instead I wallowed in my high school's educational mire until I had wasted nearly all of four years.
Having finished my four year sentence to secondary education and graduating with high marks and my belief in the educational system still intact, I began college hopeful that I would find a better learning environment, and with only a few exceptions, I did. I enjoyed most of my classes, even if I did sleep through the middle 2/3rds of nearly ever class meeting I attended, because I was learning things I was interested in: math, physics, anthropology, and computer science, my major. By my second year I was taking all upper level computer science classes, and by taking classes over the summer I was able to graduate at the end of my third year with a BS.
I don't recall what I had wanted to do with my degree when I started college, but by the end I knew that I wanted to join the ranks of academe. Both of my parents are teachers, and I have always loved to think about better ways to teach what I've learned, so combined with the promise of discovering new knowledge, the academic career path seemed ideal to me. So in my last year of undergraduate education I made arrangements to stay on at my university to earn a PhD in computer science and work as a teaching assistant for the department.
It was during this time that I lost the Way. I don't recall the exact day, but somewhere within 2004 it happened. While researching teaching methods I might find useful, I stumbled upon the writings of Alfie Kohn and Paul Graham's essays. Between the two of them, combined with my experiences in high school, my willpower broke. Not because they said anything that made me feel as though I shouldn't try, but because they made it painfully obvious that the whole point of school isn't really learning, and in some cases school's attempt to make it appear as though learning is going on actually hurts your ability to really learn. Seeing this, I came to the great realization that how I did in school didn't really matter.
As you might have guessed, this is the Dangerous Truth that I learned. It's a dangerous one because I only learned one truth, that school isn't really about learning but that you have to go through it if you want people to believe that you are as good as you claim to be. What happened to me from there should be obvious: I stopped devoting myself to my school work, worrying about its quality, and trying to be the best. The only way I stayed in graduate school was a combination of raw intelligence and and an ability to finish work to a good enough quality when under the pressure of a deadline.
After two years, though, I was pushed out of the computer science program with my MS. My university requires us to pass a qualifying exam, essentially a test of knowledge in a variety of subjects from undergraduate computer science education. Passing is more a feat of memory and determination than intelligence or ability to do academic research, so given my feelings about educational hoops at the time, I failed all of my attempts (though, I will note, I actually passed if you were to superimpose all of my attempts over one another, but I was never able to do it all in one sitting). Not knowing what else to do, and with my research already tending towards combinatorics, I switched to the mathematics department.
I'm now at the end of my third year in the mathematics PhD program. I still haven't passed my qualifiers because I am being much more cautious, maybe even too cautious, with my attempts. But I anticipate a better outcome for me this time, and that's because I found the Way again.
Between the posts on Overcoming Bias and Less Wrong, I finally got a missing piece of the truth. No matter if the intermediate steps seem dumb, if you want to play to win, if you want to follow the Way, you have to push through it if the end result is worthwhile. As it applies to my life, if I want to get that PhD, even though the qualifying exam is dumb because it doesn't test anything I haven't already demonstrated competence in and doesn't demonstrate my ability to complete academic research, it's still something I have to get through. If I want to play to win, I have to pass the qualifying exam. No more placing extra restrictions on myself so that if I fail I have an excuse: I will pass or fail by my own best efforts.
As this post suggests, partial knowledge of a powerful set of techniques can be very dangerous. It's a motif that appears in many arts. To me the most salient examples are in martial arts training and chi cultivation, but other good ones include physics, biology, AI, and economics, where applying partial knowledge could lead to real danger for the applier and the world. The Art of Rationality is similarly dangerous when only partial knowledge is obtained. It's almost too bad we can't send aspiring rationalists off to monasteries where, like ancient martial arts students, they can train and learn and keep themselves separated from the world until they have reached sufficient mastery to be safe to return to wider society.
But today most people who learn martial arts spend only a few hours a week in the dojo and maybe several more hours at home training. The rest of the time they are in normal society, possessing dangerous, partial knowledge of their martial art. Yet few of them kill anyone accidentally because the first thing they learn is where and how they are allowed to use their art. Even when tempted, it's important that the martial arts student not use what they know until they have reached a sufficient level of mastery and maturity to use their abilities responsibly in the wider world. We may need a similar approach for training in the Winning Way.
Footnotes
1 And this was even with me being in the International Baccalaureate Program, an internationally recognized college prep program that allows the transfer of course credits from high school to many universities around the world.