I would say, "Don't stress and worry so much about school or your grades, because absolutely none of that is going to matter in 10 years. Learn how to make things. Start now, and never stop. Learn how to use technology to the fullest, both software and hardware. Learn how to write, speak and communicate ideas as effectively as possible. Learn how to hack people and understand how social structures work. Take that seriously. Most importantly, don't let anyone change who you are. Choose a path and follow it doggedly."

Ironically, some of the best advice I've seen came from a book: "Who you will be in five years is determined by who you meet today and what you read today" [0]. But a 14 year old doesn't need to read a whole book to gain that particular pearl of wisdom, or many of the others. I read a lot now, several of the books mentioned on this thread and many others. But that's because I'm old, and it's too late for me. If I could talk to my 14 year old self, or any 14 year old, I would tell them that there is significantly more to life than what can be learned in a book.

[0] The Creative Habit, by Twyla Tharp

This is also a book I recommend reading, re-reading, and then re-reading again for people of all ages.

Edit: I'd also probably recommend Innumeracy[0] which is a fun book about dealing with numbers. It has some pretty great strategies for coming up with good back-of-napkin estimations which is a pretty useful skill.

[0] http://www.amazon.com/Innumeracy-Mathematical-Illiteracy-Its...

I'd recommend David Foster Wallace's Infinite Jest; Junot Diaz's This is How You Lose Her; The Collected Stories of Lydia Davis; Haruki Murakami's Colorless Tsukuru Tazaki and His Years of Pilgrimage.

I wish when I went into college I understood women better, people with mental health issues, sexuality, drugs, rich people, powerful people, old people.

He'll have 2x4 year periods where he'll be able to build long-lasting relationships. Understanding himself and other people will pay off much better than solving puzzles. So I'd stick to really aggressive contemporary fiction. He'll find math on his own.

1) Let them understand that asking any question is ok

2) Seeking answers to questions informs you about your world.

3) Anything really is possible with infinite time and money, use those goals as vectors to move your life forward.

In terms of recommendations I was pretty blown away by Buckminster Fuller's An Operating Manual for Spaceship Earth[1] as he has such a great way of looking at things differently and to pull you out of your own preconceptions.

I would also recommend an encyclopedia, because frankly it is a great way to get answers to questions and way less dodgy than trying to figure out good data from bad data on the Internet (not to mention few people have gotten into trouble getting caught with an encyclopedia in their room, which can not be said for an Internet connected computer in their room.)

Understanding how to ask questions, how to test your understanding, how to theorize and make predictions and test those theories. Those are the life skills that turn a bright child into a force to be reckoned with early in life.

[1] http://www.amazon.com/Operating-Manual-Spaceship-Buckminster...

http://en.wikipedia.org/wiki/The_Demon-Haunted_World

Also perhaps Bill Bryon's "A Short History of Nearly Everything" for an entertaining broad view of a variety of scientific areas:

http://en.wikipedia.org/wiki/A_Short_History_of_Nearly_Every...

I've also heard great things about Measurement but haven't read it myself. Another great math book that I have read is Vector Calculus, Linear Algebra, and Differential Forms, though trying to get through that at 14 would probably be a bit disheartening.

Edited to add: Also, looking back I remember how stressed I was as a teenager because it seemed like there was so much to learn and I had on idea where to begin. I wish someone had told me it was okay to not know certain things. As I've gotten older I've become much more comfortable with learning things as I need them rather than assuming I need to learn everything ahead of time. This has made my life much less stressful and much more enjoyable.

So take up meditation.

Make dancing something you do often.

Hack things with your hands.

Sing.

Sing while bicycling.

Play the harmonica with soul.

Perform your poetry to others.

Hug, kiss, and shake hands with enthusiasm.

Find people that make you uncomfortable and talk with them.

Learn a non-european language well enough to dream in it.

Audition for a Shakespeare role.

Startup a new business every three months.

Wait for sex until waiting is excruciating. Then just a bit more.

Find out what's not taught in your school and invent your own private curriculum.

Go out of your way to attend life events like christenings, bar mitzvas, quinceañeras, weddings, and funerals, for people you know and people you don't.

Yoga.

Read something non-fiction written before your great, great, great, great grandparents were born.

Make a box out of wood without power tools.

Interview older relatives and strangers like they are time travelers.

Learn to cook well enough to work in a diner.

Start a lifelong diary.

Invent a religion.

Learn all the medical names for your body parts, inside and out.

Write obituaries.

- have as many friends as you can, girlfriends/boyfriends, don't be shy, drink beer before its legal

most importantly have self discipline. If you manage to have self discipline everything else is easy in life

Looking at my own path, I agree with many of the SF suggestions (intelligent fiction of any kind os the best way to start, IMO). For me, Micheal Crichton was a huge boost to my early interest in science, objectivity, problems with the media, etc. I suspect Neil DeGrasse Tyson is a similar figure for today's generation (The new Cosmos is a great and entertaining introduction to the most fascinating aspects of the natural world).

The story of a genius child training to battle an alien species. Not only very entertaining but also critically acclaimed. It won the Hugo and Nebula and has been on several military leadership reading lists. [0] I loved it as a teenager and recently reread it and still loved it.

[0]: http://en.wikipedia.org/wiki/Ender%27s_Game#Critical_respons...

Siddhartha.

"Ready Player One".

I would also suggest, "Snow Crash" by Neal Stephenson, and would echo "Cyptonomicon".

Approaching Zero: The Extraordinary Underworld of Hackers, Phreakers, Virus Writers, and Keyboard Criminals by Paul Mungo and Bryan Clough is excellent.

The American Boy's Handy Book: What to Do and How to Do It, Centennial Edition Daniel Carter Beard

Skunk Works: A Personal Memoir of My Years at Lockheed Rich, Ben R.

and finally, which is hard to stomach sometimes.

Applied Cryptography: Protocols, Algorithms, and Source Code by Bruce Schneier

The history is only as good as was known at the time each book was published, of course, but it's better than you'll learn in school, where my classes seemed to go over the same parts of 1800s American history every year and gave no indication Asia existed.

Plus it's got sex and drugs.

When in college, try to do at least a semester abroad. Travel. If you can, join a fraternity (especially if you go to a nerd / smart school. 60+% of guys at MIT are in fraternities and they are really fantastic). Think hard about what you want to do after college and try different internships.

Work out. In high school, get into a sport - preferably Soccer or basketball (one that you can keep playing throughout your life and that is inherently social). Do it until you love it, then you'll want to keep doing it.

Learn to lift. In high school, there are likely coaches or gym class instructors offering these lessons.

Read the Dale Carengie book people mention here and try to socialize as much as possible and make friends.

Reference: I'm a guy in his late twenties, so take my advice in that frame.

It basically starts with a "code" of two friends talking to each other between houses at night via blinking flashlights, and gradually builds up from there to a full, if somewhat barebones, microprocessor, logic gate by logic gate. And it does so in a way that teenage me was able to follow.

Fantastic and thought provoking while at the same time fundamentally human sci-fi.

I would actively point teenagers away from Atlas Shrugged. While it might be enlightening, and they might enjoy the story, it has the potential to be quite destructive if they interpret her philosophy of objectivism & egoism in a way that leads them to apply it to their own lives. I just don't think this is a good idea. Her other novels, whether The Fountainhead or We The Living aren't nearly so overbearing.

Another one: How To Lie with Statistics

And Atlas Shrugged - controversial, I know, a lot of people here hate it for some reason, but it was incredibly influential on me, inspired my passion for entrepreneurship and science and philosophy. Still is one of the best books I am aware of.

If I could send 2 books back in time to the 14-year-old me - these would be it.

On a related note, I've been compiling a list myself for an even younger audience (basically all ages before 14)[1]. I bet there are a lot of influential materials for younger ages, but people don't realize how influential it was once they're grow up.

[1]: http://mcsforkids.herokuapp.com/

Gun, Germs, and Steel - For the valuable history of our culture and society.

Atlas Shrugged - for showing the entrepreneurial way and the necessity for hard work

"Mort" and "Reaper Man"; "Guards! Guards!", "Men at Arms", and "The Night Watch"; "Wyrd Sisters", "Witches Abroad" and "Lords and Ladies"; and "Small Gods" and "Pyramids".

The first two are about Death, the second three about Samuel Vimes, the third group about Granny Weatherwax, and the last two are stand-alones. All the books are worth reading, but those are some of the most engaging and compelling, and they teach skepticism, humanity, kindness, courage and absurdity in equal measures.

It's great to have deep focus (especially if you're in science and tech), but all the other stuff -- especially any creative arts you can actually perform with your own lung, lips, muscles and tongue -- can bring great benefits also; not just intellectually, but in terms of building and sustaining a basic, intrinsic sense of self-worth and confidence in a world that seems hell-bent on tearing it down every turn.

That -- and of course: meditate.

It feels like biotech is where computing was in the 1930's... what's to come, and how it will change the world is both frightening and exciting.

On the "soft" side (whatever that means): ethics, the history of ethics, from every point of view.

Two lecture series I always recommend, and feel like everyone should watch with a gun to their head (as the instructor himself says):

- https://www.youtube.com/watch?v=kBdfcR-8hEY -- Harvard course on justice / ethics.

- https://youtu.be/NNnIGh9g6fA -- Robert Saposky (and guests) on the biology of human behavior.

Literary theory. Gaining a deeper understanding of how masters of symbolism, language, and creativity think and put together their work; the history of literature; etc. will open you up to new ways of thinking just like studying pure maths or programming would.

Now to invent a time machine and give myself this advice! Boy I could've used it.

http://www.amazon.com/s/ref=nb_sb_noss/189-1683403-2668213?u...

When I homeschooled my sons, we used several of them. The Cartoon Guide to Statistics -- we did like the first chapter or two. I had had college statistics. Most of the book was over my head.

They are kid friendly, though not really intended for kids, so there is sometimes off-color humor. However, they are not watered down. They are very meaty approaches to the subject that also make the subjects approachable. They cover things like physics, genetics and other serious subjects.

Also:

The Number Devil: A Mathematical Adventure

Reading this with my sons is the first time I had heard of Fibonacci numbers and I had a lot of math in high school.

Also also:

A Tour of the Calculus.

I can't recommend a specific book in these categories (since I have learned mostly independently), but I would look for good books which cover: Music Appreciation and low-level Theory, Philosophy (especially Eastern), and Argumentation and Logic.

But then again, I might be biased since I'm the author ;)

Another thing that would be useful as an introduction to computing is this SymPy tutorial that covers many manth topics that highschoolers are familiar with: http://minireference.com/static/sympy_tutorial.pdf

[0] http://www.vanadac.com/~dajhorn/novelties/ESR%20-%20Curse%20...

Extrapolating a bit from that lesson, and with ~40 more years of hindsight, I'd highly recommend that a bright 14 year old read some books that give a broad overview of science & philosophy, and establish a thorough understanding of the scientific method. One that I happen to be reading right now that I feel is remarkable is David Deutsch's The Beginning of Infinity. Deutsch is a theoretical physicist at Oxford working on Quantum Computation. The Beginning of Infinity (despite the new-agey sounding name) is an incredible work.

Another book I highly recommend is Richard Dawkins' The Selfish Gene, not just for how it explains Neo-Darwinish, but because of the chapter on Memes. Deutsch also has a great treatment of Memes.

The first three books of the Earthsea cycle by Ursula K. LeGuin.

These both skew young but I valued re-reading them as I got older:

The Dot and the Line: http://en.wikipedia.org/wiki/The_Dot_and_the_Line

The Phantom Tollbooth: http://en.wikipedia.org/wiki/The_Phantom_Tollbooth

[0] http://en.wikipedia.org/wiki/The_48_Laws_of_Power

The Hacker's Dictionary: http://catb.org/jargon/ -- was similarly influential in my finding the joy and excitement in software development. I had come to enjoy it on my own already, but reading this (in printed form, at the time) helped me get a broader perspective. It's admittedly quite outdated now, but I'm not sure what a newer replacement might be.

How about an intro to IOS/android programming?

For fiction, it's damned hard to say. My own personal top influences in fiction form were the Young Wizards series by Diane Duane and, weirdly, the anime/manga Tengen Toppa Gurren Lagann. It's actually very, very hard to find good fiction for kids, since you're trying to inspire or teach rather than just entertain. Terry Pratchett's Tiffany Aching arc is good for younger kids, with the later books having the star character as a young teen.

For nonfiction that isn't just math/science/technology, how about the Communist Manifesto?

Don't hate things simply because of how you perform. Love it even when you suck at them.

Don't criticize more than you praise ... others. Don't praise more than you critique ... yourself.

Don't judge the ability of others in comparison to yourself. You were lucky to have the opportunity they probably were not. And they probably were lucky to have the opportunities that you were not.

Everyone is bright. Everyone is smart. Few have the opportunity to show it. Few have the opportunity to feel it.

The only true differentiator between people: how hard you work and how long you hope.

hpmor.com

Reading the original helps and adds to the experience, but is not necessarily required.

"Mara and Dann An Adventure "

I would recommend it because I believe people in those fields write with a very interesting perspective, and also because they write about things which may be more broadly interesting to varied people, and with a narrative form that is more accessible than other fields, and they still write with less censorship than what a young person might be used to.

Such writing also affords a level of respect to the reader that a young person might not be used to. This is the important part. Young people are often exposed to worldly, societal, behavioral, moral, or philosophical matters through authors who yank around the story in any way they please, such as with "Fahrenheit 451", "Brave New World", or "Lord of the Flies".

In my opinion, these young people are being intellectually disrespected without knowing it. Always exposed to a kitsch view through a highly obscured lens with a penchant for melodrama. It's a world of non-seriousness where everything is just opinion, and what's important is to express how you think anything works. Some people grow into adult versions of this.

But when you read what adults think about the phenomena of bullying and predictors of victimhood, it's a little bit different. Or when you read about childhood predictors to different adult styles of drug use, you start viewing things a little different. Or when you read of how a team of adults performed brain surgery on a songbird to investigate human behavior, you start viewing things a little different. You also start seeing the severity of prediction.

Maybe it's a bit cold in doing nothing to shield the reader from the perspective of the writer, but almost never tactless. And it's very respectful to the reader. It might be the first time a young person isn't spoon-fed a highly obscured and Hollywood-ish discussion about the world.

Now the rest.

One lesser-known book that made a deep impression on me: A.K. Dewdney's "The Planiverse", a kind of Flatland-meets-the-MIT-hackers story. How would architecture, biology, and chemistry work in a 2-dimensional world?

Sagan's "The Demon-Haunted World" was an important book for me, but I read it when I was a couple years older than 14.

SICP, if the 14-year-old knows basic programming and has written a few 1000-line programs. I wouldn't have understood it at 14 but enjoyed it tremendously at 18.

I'd recommend to a 14-year old an AI camp being offered by the Stanford AI Lab: http://ai.stanford.edu/sailors/

  - Common Sense
  - On Liberty, Mill
  - Connections. the book or the video, Burke
  - The Day the universe Changed, Burke, I think this is only video
  - If into history, The Federalist Papers. Amazing how often you hear someone say "the founding fathers..." then something that contradicts what they actually said and wrote.
  - The People Shall Judge, Collected historical writings, The University of Chicago Press

[0] https://smackernews.com/item/4273012 HN

http://www.amazon.co.uk/Progress-Poverty-Industrial-Depressi...

Make friends with someone who challenges you. Play some kind of sport, preferably a team sport. Learn to cook. Learn a musical instrument if you're so inclined. It wouldn't hurt you to work as, say, a dishwasher, for a year or two.

Source: I was a bright 14 year old decades ago, and I'm picking my favorite hits and misses.

Starting Strength by Mark Rippetoe

Drawing on the Right Side of the Brain by Betty Edwards

The Little Schemer by Friedman and Felleisen

Literature, for starters:

Heinlein's earlier works

Anything by Asimov

1984 and The Animal Farm by Orwell

Detective novels by Doyle or Christie

Hackers by Steven Levy

Far and away, the best for a young person coming into adulthood. In an age appropriate manner and wording (vocab, tenses, allusions to other works, etc) Hatchet explore what it takes to mentally be an adult. Brian's near suicide and rebirth alone in the Canadian forests is a classic story in literature, and it is no where else better played for young adults than in Hatchet. Brian's personal choice to live and be self sufficient against the odds is a great lesson for that age. The epilogue is masterful as well, and I'm sure, took a lot of guts to publish as-is and not re-write.

Other great books (with amazon links) can be found here: http://www.artofmanliness.com/2009/06/02/the-essential-man%E...

The follow up from that blog's readers can be found here: http://www.artofmanliness.com/2013/05/21/fiction-for-men-as-...

Note: The linked blog focuses more on the 'classical style' in western literature and thought. By classics, I mean true classics from the Enlightenment and Greek and Roman works, not devoid of racism or sexism, sometimes in full acceptance and joy of those evils. Nonetheless, I feel most of those books are great reads, if the young person is given caution and some guidance on how to handle the differences between our forefathers' views and ours'.

EDIT: Additionally, look into language learning courses. Duolingo (https://www.duolingo.com/) is free and amazing (nothing beats having cousins in Italy or Mexico, though). At 14, the brain is still pretty plastic and able to learn languages a bit easier than us old'uns.

I have been amiss for not linking to the above blog's other non-fiction lists and movie lists: http://www.artofmanliness.com/2008/05/14/100-must-read-books... http://www.artofmanliness.com/2009/07/13/100-must-see-movies...

I'll also act like a shill here and advocate for youth organizations like the BSA. Here is a nice tool to find a troop near you :http://www.scouting.org/LocalCouncilLocator.aspx . I know I may get some flak from HN here for BSA advocacy, but I had a great time on the road to Eagle and the Scouts are updating. Also, many councils are in open defiance of the policies (naming names is hard to do here, it is necessarily kept mum). Please, give them the time they need.

[0] 'Top Books Derived from 11 "Top 100" Lists', http://www.reddit.com/r/books/comments/1iw3jq/top_books_deri...

This was a very influential book for me in just thinking about what it would be like to do math for a career. And I'm not a mathematician, so I think it worked. :-)

    - Book of the Subgenius 
    - Meditations, Aurelius 
    - Slaughterhouse-Five, Vonnegut 
    - Blue and Brown Books, Wittgenstein 
    - Stranger, Camus 
    - Dhammapada, Buddha
    - Thus Spake Zarathustra, Nietzsche 
    - Blue Cliff Record, Kequin
    - Trial, Kafka 
    - Labyrinths, Borges

Mindstorms by Seymour Papert

Design of everyday things by Donald Norman

Really, a blank slate and a promise to help them with whatever they want to learn.

http://www.amazon.com/Misteaks-find-before-teacher-does/dp/1...

http://www.carlhiaasen.com/young-readers.shtml

Basically, anything that's good quality and fun to read.

Learning to enjoy reading is more important than any specific skill you can teach.

Modern school reading lists suck donkey balls.

* hofstadter's "metamagical themas"

* the entire discworld series

And as practice, take a job as a door to door sales person. Build up resistance towards rejection and learn how to influence people.

http://en.wikipedia.org/wiki/David_Deutsch#The_Fabric_of_Rea...

Essentially start with the classics of philosophy. Its my biggest regret I wasn't introduced to them as a child.

Actually I am recommending this book to every human being regardless of your age.

Frans P.B. Osinga - Science, Strategy, and War: The Strategic Theory of John Boyd

Buddhist precursors and a pile of Koans.