Probably How to Win Friends and influence people. I could have done with being nicer to people much earlier in my life, probably around 12 or so.
I'm surprised by the number of tech books on this list, I found I had an appetite for finding them myself pretty much when I was ready for each of them.
When I was about 17 I was told, in no uncertain terms and by someone I respected: "You really need to learn how to get along with people."
I took that at face value, and tried to find a manual for how to interact positively with others, and I found H2WF&IP.
I treated it like a text book, and it changed my life completely. I was happier, more able to be sociable, and I could get along with people.
Now, after a further 30 or more years, I can still see the book's influence as I negotiate deals, manage employees, broker agreements, and generally "do stuff."
It's now out-of-date, but if you can make the effort to read it in the context it was written, and to ignore the obvious anachronisms, it's still valuable. The more recent versions try to be more up-to-date, but they lose something as far as I can tell, and I return to the original.
I'm 16 and picked that book up just before my 15th birthday. Well worth the read, and would recommend it to anyone. Going to give it a reread now, thanks for the reminder!
An obvious technical one: The Structure and Interpretation of Computer Programs. That might have saved me a lot of time to read in early adolescence. (Or maybe it was better to have to figure things out in my own half-assed way. Time travel is tricky.)
But something like Francis Bacon’s Essays might be more important. Seeing that lively and methodical a mind right at the horizon of easy readability would have been a powerful clue about how people think and how far afield it’s useful to look for interesting things.
Any math books would have been nice. Shame to discover math now, when I'm in college. I overestimated the complexity of college math; there was a lot of handwaving in highschool about how demanding college will be, turns out it was all bull, all it served to do was discourage me from learning something. My own fault for listening, even half-heartedly, to high school people.
There is no single book which adequately describes my thinking. Rather, I would encourage him to read more in general, whatever he was curious about. Only through understanding a wide variety of classics and perspectives does one become educated. There were quite a few years where I did not read much at all, and I regret that, because I'm stupider for it.
I would also give him the practical limitations of only trying to read one book at a time, to take his time with it, and to start a new one not long after finishing. Then again, I'm not sure I should mess with the space-time continuum.
K&R. I discovered the book at age 17 by myself but that was the book I really wanted when I was 12. Not just because it teaches C -- it teaches the core of the systems programming and design experience. If you're interested in systems development I can't recommend K&R enough. You haven't really been taught C until you've been forced to implement malloc in C.
"A Transition to Advanced Mathematics" (0-534-38214-2) at the end of my 6th grade school year, just as summer was starting.
I would give this book to myself because it's a bridge between finishing the final class in high school math and learning how to read proofs on arXiv. The world would be a better place today if I'd known how to manipulate mathematical proofs a decade ago.
During fourth grade and fifth grade, i walked across the street to the other school for my math classes. To this day, people i never knew recognize me on sight as "that kid from math class". When sixth grade ended at age 12, the school ran out of math to teach me (at pre-calculus). I was offered a choice: bus to the high school miles away for math classes, or take music instead. I worried that the bus would ostracize me further from my peers. I would be someone else today if i had chosen the bus. Fluent in math, certainly!
In the years since, I've harbored a desire for a textbook that will teach advanced mathematics to someone with my experience. I've had this dream of understanding how to consider and construct equations with Hilbert spaces. I know it sounds arcane and weird, but it's just a few steps away from cosines and bitwise operators. You can reach into an equation and "flip" things over into this weird space with dimensionality that is not constant, enabling solutions that cannot be had simply from high school algebra alone.
Two months ago, while surfing a used bookstore's Math section, I came across a textbook with the singularly direct title "A Transition To Advanced Mathematics". It is amazing. I am reading sections, doing the exercises, checking against the teacher's guide, redoing until I get a right answer or at least "get it". So far, I can handle one section a week, which means I will complete the book in 39 weeks. (Coincidentally, 39 weeks is precisely 75% of a year, just like American school years.)
Probably "Man's Search for Meaning" by Victor Frankl... Although I'm not sure that the book will have the same impact without the accompanying life events.
So short of that, i'd give my 16 year old self the missing pages from the Dabs C book which I spent far too long trying to figure out!
I think I read Paul Graham's essays when I was 18. I can't imagine diving into startup world any earlier than that. After all, had to enjoy my teen life!
Any way, if I really must, I would have given back 'Founders at Work' to my 18 self. I only got to read it once I was 21.
My younger self wouldn't have been interested in the books that interest me now. Instead I'd have to settle for some good fiction.
Going back in time to around 12-16, I'd send one of:
* Brave New World - Aldous Huxley
* 1984 - George Orwell
* To Kill a Mockingbird - Harper Lee
* Catch 22 - Joe Heller
* Slaughterhouse Five - Kurt Vonnegut
* Of Mice and Men - Steinbeck
* Fahrenheit 451 - Ray Bradbury
* The Call of Ctulhu - H.P. Lovecraft
* Ender's Game - Orson Scott Card
Some of those I actually read in school and loved (but wish I read earlier), others I didn't. I think any of those books would've interested me at the time. There's plenty of time for Rich Dad, Poor Dad, SPIN Selling and all the business books later in life.
Atlas Shrugged. I'm not a Rand groupie but seeing some of the core ideas of what I always felt but never could quite articulate literally changed me as a person.
I think my father tried this exact experiment with me. He gave me a copy of Atlas Shrugged when I was twelve and asked me to read it and tell him what I thought.
Neither of us were (or are) objectivists, but it's one of those books that poke your buttons. Either you agree[1], you disagree[2], or you think it's insipid[3]. :-)
[1] Yeah, screw those looters who aren't as smart as I am! I mean, he is!
[2] Jeez, I hope someone drops a rock on these anti-social bastards. And what a floozy!
[3] You needed 80 pages for that speech? Weren't you reading this book while you wrote it?
Nassim Taleb's The Black Swan. At 17 I thought there was nothing that couldn't be achieved by shear will and concentrated effort. The Black Swan introduced me to the notion of Mediocristan and Extremistan, two very different domains with entirely different sets of risk. I don't think I'd have done anything differently, but had I read it earlier, I'd probably not have beat myself up so much when things didn't go well.
I had a whole lot of ideas when I was younger. I made a lot of mental plans for world domination.
I think something by someone like Brian Tracy, on getting started, would have been good. Start something. Start today. Fail. Fail often. Much better than the 'wait till you have planned yourself to death' advice I got when I was a kid.
'The Fountainhead'. It would have assured me that there were many other people with the hacker mindset (which ultimately is what the book is about), it would have helped me prepare for a world where that mindset was not the norm, and hence would probably have avoided years of agony and depression later.
Seven Habits of Highly Effective People by Stephen Covey. I read this book during college, but I wish I had read it earlier in my life, like when I was in junior high. This book set my priorities straight.
I agree completely with The Gay Science, although I may have wished for an accompaniment. But really, Atlas Shrugged? Nietzsche and Ayn Rand just aren't even playing the same game.
Getting Things Done - since reading it in the spring, it's changed the way I approach projects. I would have been SO much more productive when I actually had time to kill in my 20s.
I would give myself every newspaper from now until back then so I couldve known every lottery ticket number and sports score so I could gamble and be a billionaire. =)
I'm surprised by the number of tech books on this list, I found I had an appetite for finding them myself pretty much when I was ready for each of them.