I will recount my experience.
Spend high school overachieving (probably at the expense of social development)
I didn't overachieve in High School because I realized how pointless an effort that was. There were only 2 things I cared about in High School, and that was Computer Science and Math. I realized this by about grade 5.. At that time, there was a little orange book called "Games in Basic" on my teacher's bookshelf. I picked it up and started reading it one day and was fascinated (we had a PC with Windows 3.1 and I could easily boot into DOS and code up basic games). She saw me reading it and said "I bought that thinking kids might like it but nobody but you has ever read it, so you can have it if you want." So I took it home and went through all of the exercises in it (just basic word games, input a number/word, output a response, etc). At that point I was hooked. When we finally upgraded to Windows 95/98, I started playing around in VB, eventually installing my father's copy of VC and learning C. This is where my time not in school was spent (split between that and playing games). I quickly realized I enjoyed this more than just about anything else, and so I did it. I taught myself VB then C then x86. By the time I could actually take a CS course in High School I was a junior, and it was an entry-level Java course. I still learned things -- data structures and some algorithms, but the majority of the syntax and other things I was quite familiar with already. Of those two categories I cared about, I maintained a 95%+ average. I didn't apply myself in History, English, other sciences, or any of the nonsensical electives we had to take. I saw no reason to, and I didn't care that I was just outside the top 10% mark in my school, nobody I knew was as good at Math or CS as me, so as far as I was concerned, I was the valedictorian. When I later spoke with people in the top 1% including the actual valedictorian, the arrogance they exuded was astonishing, as if they had accomplished something worthwhile.
work hard and get into a great college, get knocked down a peg when you realize that you're either somewhere in the meaty part of the curve among other prospective engineers, or that you'll actually need to *try* in order to get that A for the first time in your life
I didn't work hard to get in a great college, but I still managed to, even with my crappy GPA (something like 3.4 in HS), get a scholarship to a local university. I really wanted to go to Stanford or MIT, but the money just wasn't there, and a huge student loan wasn't something I could justify. So I majored in CS, an obvious choice, and figured that this 4-year degree would do nicely in the real world, where experience is more important anyway. I realized pretty quickly that the CS curriculum there wasn't challenging. I could read through the texts and learn what a course would teach me in a few days, and would end up bored sitting in a course going at a snail's pace for the rest of the semester. On the other hand, math courses were actually quite challenging. So 3 semesters in I switched from CS major to Math major and still took the interesting CS courses in my electives (compilers, AI, operating systems, etc). The math courses were a fair bit more difficult, especially more abstract courses, but the only time I actually had to really try to get a decent grade was when I finally started taking graduate courses. There's just too much information to keep in one's head to fully understand why a proof is valid (it doesn't just span that chapter in that book, nor even that entire book, but rather the past 3 years of courses of abstraction). Needless to say, in my spare time, I was still hacking around in CS and my brain was already prioritizing CS-useful math (including things like Abstract Algebra, Number Theory, Probability, etc), but the rest was reserved for actual CS work, so I wasn't to interested in pursuing an M.S. in math. No CS course I ever took was difficult, but I do suspect at MIT or Stanford that I would have been really challenged to make a good grade -- maybe one day I'll get around to getting an M.S. or a Ph.D. from either. It was at this point that I started reading the references in my texts and finding things I was particularly interested in, following references on Wikipedia, and reading articles in peer-reviewed journals my university had subscribed to. I very quickly realized what I knew is like a single point on the 2D plane, and similarly what we all know, collectively, is merely a single 2D plane within 3-space. It's astonishing when you actually open your eyes.
once you do succeed (or maybe just fail to fail) you graduate college thinking you're ready to take on the world... enter the business world and realize that the fancy education you paid so much for is only good enough to get your foot in the door...come to the realization that respect is earned by experience and demonstrated value... spend a few years building up credibility and expertise, then realize that being a manager (or director, or VP, etc.) requires some serious people skills (remember all those parties and extracurricular activities you skipped in high school in favor of hacking and video games?) and either choose to stay on the individual contributor path and hone your skills to guru level or take the plunge and start educating yourself (both formally and informally) in how to effectively manage a bunch of cocky engineers.
I'm still in the initial stages of the business world, but I've already realized I was lucky enough to be correct when it came to my educational choices: the school doesn't matter, and after a few years, your experience trumps it anyway. I also have made a decision already, and that's to never become a manager. I don't want to manage people, I want to be an engineer. Any company where the only way to "advance your career" is by changing your role entirely from an engineer to a manager is by definition not a company I want to work for. It's too bad that vision is so pervasive in this culture. Hackers want to hack. We don't want to go to meetings, read thousands of e-mails, or talk to "senior managers", "VPs", or "C*O"s outside of showing them our awesome hacks. That's all. I don't think I have a lot of arrogance these days. I definitely did when I was younger, but sometime around 22-23 a switch flipped and it was gone almost over night. Maybe it's the change from looking at everything subjectively to looking at everything objectively. Maybe it's the realization of how little you actually know. Maybe it's the realization that you no longer have to demonstrate that you're "smarter" than other people (a mentality put in place by schools via grades and grade-curves, we are competitive beings). Maybe it's because now when I look for information, I have to wade through a sea of information to find that little drop I care about versus consuming all information available in my text book and thinking: "is there more? Do I know everything about this topic now?" Maybe it's a combination of all of those things -- but I don't think there's a "fix" for it, other than letting someone eventually figure it out.