And, no, not Ayn Rand
May 11, 2010 11:12 AM   Subscribe

So, what were your big life-clarifying books?

My son is 18 and has hit one of those rough patches – he is struggling with questions of what he will do with his life, what it means to be successful, how to successsfully navigate ill-fitting societal norms, etc. They are questions we al grapple with and are very age-appropriate, but he is having a hard time dealing with them and is feeling adrift. We talk about it a lot, but I would like to find some outside, non-parental sources for him. I remember several book that were important to me, Zen and the Art of Motorcycle Maintenance and Siddhartha to name two – but sad to say, I don’t remember exactly what questions they answered for me. Plus, my issues at his age were largely social, his seem to relate more to direction and career.

So, does anyone have any good suggestions for books that could change his life?
posted by rtimmel to Religion & Philosophy (92 answers total) 146 users marked this as a favorite
I read Ishmael when I was about that age.
posted by decathecting at 11:19 AM on May 11, 2010 [4 favorites]

I was in love with Portrait of the Artist as a Young Man at that age. The critical edition is good because it gives a lot of the social/historical context that's fairly crucial.

On a different note, I also responded very strongly to Marcus Aurelius's Meditations around the same time.
posted by scody at 11:30 AM on May 11, 2010 [1 favorite]

Previously, though the question doesn't exactly matches yours.
posted by cranberrymonger at 11:31 AM on May 11, 2010

Jack London's The Cruise of the Snark

"Our friends cannot understand why we make this voyage. They shudder, and moan, and raise their hands. No amount of explanation can make them comprehend that we are moving along the line of least resistance; that it is easier for us to go down to the sea in a small ship than to remain on dry land, just as it is easier for them to remain on dry land than to go down to the sea in the small ship. This state of mind comes of an undue prominence of the ego. They cannot get away from themselves. They cannot come out of themselves long enough to see that their line of least resistance is not necessarily everybody else's line of least resistance. They make of their own bundle of desires, likes, and dislikes a yardstick wherewith to measure the desires, likes, and dislikes of all creatures. This is unfair. I tell them so. But they cannot get away from their own miserable egos long enough to hear me. They think I am crazy. In return, I am sympathetic. It is a state of mind familiar to me. We are all prone to think there is something wrong with the mental processes of the man who disagrees with us."
posted by matty at 11:33 AM on May 11, 2010 [1 favorite]

I'm gonna chime in with the angsty Nietzsche, Catcher in the Rye, Confederacy of Dunces angle, but I'm also the kind of guy who thinks "direction and career" are the fruits of ironing out a "largely social" conversation one has with oneself between the person you are and the person you want to become.
posted by rhizome at 11:34 AM on May 11, 2010

Ishmael is great.

Stranger in a Strange Land was a super read the summer after I graduated high-school.

I think I read Fahrenheit 451 and it was a super read, especially in our ever-connected world and I identified with the disconnected nature of the lead character.

Of course, it's always the right time for Hitchhiker's Guide to the Galaxy.
posted by Hiker at 11:36 AM on May 11, 2010

Maybe not the precise subject matter you're after, but a big life-clarifying book for me when I was around your son's age was Illusions - The Adventures of a Reluctant Messiah.

(Yeah I know, Richard Bach, Jonathan Livingston Seagull, pseudo-intellectual blah blah blah... Illusions is a good book and it helped me through some tough times when I was a young man trying to figure out my place in the world.)
posted by Balonious Assault at 11:37 AM on May 11, 2010 [2 favorites]

Oh, and Viktor Frankl`s Man`s Search for Meaning is a great read if you`re feeling adrift.
posted by Hiker at 11:38 AM on May 11, 2010 [4 favorites]

I found, and am still finding, that reading books about people who have found a career direction they love, and especially those who found it later in life (and the path they took before it), can be inspiring and comforting. Mountains Beyond Mountains, about Paul Farmer, came to mind immediately.
posted by telegraph at 11:38 AM on May 11, 2010 [3 favorites]

Going After Cacciato by Tim O'Brien. I only read it for something to do while I was stuck with my family for my freshman-year spring break, and O'Brien was coming to my college to read/speak. It absolutely changed my life, in that I had always thought from a young age I'd be a psych major/social worker, and I ended up changing my major to English and having a successful career as an editor.

Besides the practical impact the book had, it was the first time I really understood that you could create your own reality, that the hand you were dealt didn't have to be the hand you played (or at least you didn't have to play it in the expected way). There's a lot to that book and I've read it several times since and it not only holds up but grows deeper and more meaningful on rereading.

The Things They Carried is commonly thought of as O'Brien's best work, and believe me it touched me as well, but Going After Cacciato is literally about a man blazing his own trail in the world and that was a pretty powerful idea to this particular sheltered suburban Catholic 18-year-old.
posted by headnsouth at 11:38 AM on May 11, 2010 [1 favorite]

Robinson Crusoe by Daniel Defoe. (So much better than anyone who hasn't read it as an adult realizes.)

Crossing to Safety by Wallace Stegner

Herzog by Saul Bellow

Grace Beats Karma: Letters from Prison 1958-60 by Neal Cassady
posted by The World Famous at 11:39 AM on May 11, 2010

Above all, I recommend The Conquest of Happiness by Bertrand Russell, which covers all the issues you mentioned.

More about career/life:

- What's It All About? by Julian Baggini

- Flow by Mihaly Csikszentmihalyi

- the first two chapters of Mortal Questions by Thomas Nagel ("Death" and "The Absurd")

- Stumbling on Happiness

Here are some about "ill-fitting societal norms":

- The Will to Change by Bell Hooks (an avowedly "radical feminist" take on problems unique to men and boys in society)

- The Moral Animal by Robert Wright (the biological roots of social norms)
posted by Jaltcoh at 11:40 AM on May 11, 2010 [2 favorites]

I'll second Stranger in a Strange Land. It's a deeply problematic book in a lot of ways, but I consider it the formative book of my teen years,
posted by marginaliana at 11:43 AM on May 11, 2010

Not a novel but: Who Am I For Myself? Anxiety & the Tyranny of Choice.

This was very helpful to me in understanding how the cultural imperative to self-construction is the very form of our inclusion in global capitalism and actually a form of oppression. The anxiety and dissatisfaction he feels is a problem with the system, not a problem with him.
posted by AlsoMike at 11:48 AM on May 11, 2010

Vonnegut, especially Cat's Cradle and Slaughterhouse-Five.
posted by oinopaponton at 11:49 AM on May 11, 2010 [7 favorites]

Earth House Hold, by Gary Snyder.

It gave me a way of seeing, especially when traveling.
posted by Danf at 11:50 AM on May 11, 2010

In the Hermann Hesse oeuvre, I found Demian a lot more helpful at that age than Siddhartha.

I also found Fitzgerald's This Side Of Paradise comforting at that age, not because it gave much guidance but because it confirmed that it was normal and maybe a little romantic to be young and not yet know what to do with myself (the last line of the book was a favorite - "I know myself, but that is all!")
posted by bubukaba at 11:50 AM on May 11, 2010 [1 favorite]

Infinite Jest.
posted by The Michael The at 11:51 AM on May 11, 2010 [4 favorites]

Lost in the Cosmos by Walker Percy
I Am a Strange Loop by Douglas Hofstadter
posted by rikschell at 11:53 AM on May 11, 2010

Mountains Beyond Mountains and Ishmael are both great, but the one that changed my course was Franny and Zooey by Salinger.
posted by youcancallmeal at 11:56 AM on May 11, 2010 [2 favorites]

Hesse's Peter Camenzind and the incredible Magister Ludi.

Zen in the Art of Archery.
posted by jgirl at 12:02 PM on May 11, 2010

Future Shock - by Alvin T.

How to win friends and influence people - by Dale Carnegie

The book has six major sections. The core principles of each section are quoted below.

Fundamental Techniques in Handling People
Don't criticize, condemn, or complain.
Give honest and sincere appreciation.
Arouse in the other person an eager want.

Six Ways to Make People Like You
Become genuinely interested in other people.
Remember that a man's Name is to him the sweetest and most important sound in any language.
Be a good listener. Encourage others to talk about themselves.
Talk in the terms of the other man's interest.
Make the other person feel important and do it sincerely.

Twelve Ways to Win People to Your Way of Thinking
Avoid arguments.
Show respect for the other person's opinions. Never tell someone they are wrong.
If you're wrong, admit it quickly and emphatically.
Begin in a friendly way.
Start with questions the other person will answer yes to.
Let the other person do the talking.
Let the other person feel the idea is his/hers.
Try honestly to see things from the other person's point of view.
Sympathize with the other person.
Appeal to noble motives.
Dramatize your ideas.
Throw down a challenge & don't talk negative when the person is absent, talk about only positive..

Be a Leader: How to Change People Without Giving Offense or Arousing Resentment
Begin with praise and honest appreciation.
Call attention to other people's mistakes indirectly.
Talk about your own mistakes first.
Ask questions instead of directly giving orders.
Let the other person save face.
Praise every improvement.
Give them a fine reputation to live up to.
Encourage them by making their faults seem easy to correct.
Make the other person happy about doing what you suggest.

If you only take one thing out of this book, adults and kids always have trouble with this, but learn to listen to other people.
posted by MechEng at 12:05 PM on May 11, 2010 [23 favorites]

I came here to post Man's Search for Meaning, but Hiker beat me to it. Frankl (and his translator) do a wonderful job of addressing some fundamental questions in a really approachable and accessible way. It's also a short read, and you still get quite a bit out of it even if you only read the part about Frankl's experiences in the death camps and skip the part where he lays out his theoretical approach to psychotherapy (I read and enjoyed both, for what that's worth.)

I don't know if it'll help your son in terms of finding a vocation, since it's more general than that, but it might help him feel less adrift as a human being trying to find his way in a confusing and sometimes disheartening world. I consider it one of my fundamental books and return to it every few years.
posted by Kosh at 12:05 PM on May 11, 2010 [1 favorite]

When I was a kid, Madeleine L'Engle's A Wrinkle in Time and the two sequels was really important for giving me a clue that there was more to this than what I had thought. Your son is probably past that phase though.

The Hitchhiker's Guide to the Galaxy Trilogy (as it was at the time) got me through adolescence. Having Douglas Adam's voice in the back of my head made a lot of the absurd situations I went through tolerable.

Slightly later, towards the end of high school, The Stranger by Camus was important to me. Some people find that book nihilistic, but I find Camus brutally life-affirming. I suppose that's the basic contention some people have with Existentialism though.

I'm a big fan of Zen Mind, Beginner's Mind, and strangely don't own a copy...I'm always giving that one away.

These days, the book that is probably most important to me for guidance--perhaps because it leaves so much open and forces me to re-focus on what I'm really trying to understand--is the Tao Te Ching, particularly this translation.
posted by dubitable at 12:07 PM on May 11, 2010 [1 favorite]

The Sirens of Titan
posted by Jezztek at 12:08 PM on May 11, 2010 [1 favorite]

I'm going to go a different route than the rest of the posters, although all the suggestions above (that I've read) are good.

What really focused my mind in late h.s. / early university was reading a number of books about Rwanda. Primarily, Shake Hands With the Devil by Dallaire, and We Wish To Inform You That Tomorrow We Will Be Killed With Our Families by Gourevitch.

Reading about the real world and its failings might be the impetus to choose a direction that helps fix it. And it definitely redefined what it meant for me to be happy.
posted by Lemurrhea at 12:15 PM on May 11, 2010

By 18 I'd read the books you mention a couple of times I think. Around then I was reading Carlos Castaneda's books. It was intensely muddying and sometimes terrifying at first, but as I later learned about buddhism, zen, and daoism and understood what Don Juan had done to him, they became more and more informative. I think it's time for another read, in fact. I might recommend a different path... how about Kalil Gibran books, if he responded well to Siddhartha? I think The Prophet comes first, but I'm not sure. I read it first. It's very abstract in talking about these things in kind of the same tone as Siddhartha.

Another one is Knots by R.D. Liang. It comes off as a book of poetry, but it's a compendium of the kinds of inner dialogues we get bogged down in that make no sense and limit us.

Incidentally, I'd read a lot of Vonnegut around the same time, and, with recent re-readings, found that I didn't even have the barest understanding of them.

Also, I was gonna plead with you not to give him any Rand, but I see you've got that covered. On the other hand, I've thought of it as pretty important that I read and identify with books like Anthem and Cather in the Rye as an adolescent because it gave me a chance to pin down and then grow out of the kind of thinking those kinds of books talk about.
posted by cmoj at 12:15 PM on May 11, 2010

You're asking for books where Big Thinkers ponder Big Questions in Big Ways.

Sometimes, the answer is much simpler. Sometimes, the answer to the Big Questions are found in a preponderance of smaller things. Think about Thoreau -- in his time, everyone thought the Answers to Everything were in the Bible, or places like Harvard and Yale and West Point. So Thoreau went into the woods.

Look elsewhere. Give him a ripping fictional yarn with a modern spin, like Snow Crash. Or a ripping non-fictional yarn, like Lost Moon. Or something up-to-date and newsworthy, like Fiasco. Or heck, even a business book that urges you to attack things differently.
posted by Cool Papa Bell at 12:15 PM on May 11, 2010

Ooh, nthing Cosmos, especially if he's at all interested in science or academia. It's about a lot of different things, but I always read it as a love letter to passionate nerds everywhere.
posted by oinopaponton at 12:16 PM on May 11, 2010

I would have loved a set of Brian Eno's Oblique Strategies cards when I was in that phase. I'd kinda like one now, if anyone's feeling generous.
posted by mattholomew at 12:17 PM on May 11, 2010 [1 favorite]

I graduated high school last summer and I read The Tao of Pooh. Absolutely amazing in terms of "what should I do with my life?" and all of the anxiety that accompanies a huge life shift.

It's especially wonderful in terms of Cool Papa Bell's comment about simplicity--it answers the Big Questions in the Simplest Ways.
posted by allymusiqua at 12:26 PM on May 11, 2010

Yeah, what does this kid like to read? What are his interests? I could hand my obnoxious youngest nephew a copy of something deep and profound, and he'd throw it across the room and go play Mario Kart for three hours... so I settled on Ender's Game and a handful of other books that were more subversive than they were Great Books.

Very generally, for fantasy, I'd recommend American Gods by Neil Gaiman. SF, Old Man's War by John Scalzi (although Snow Crash would work too, as Cool Papa Bell said). I've got a boatload of comics recommendations, but I'll hold off because you specified books and not sequential works. Knowing something about his interests would help us tailor recommendations.
posted by fairytale of los angeles at 12:26 PM on May 11, 2010

Infinite Jest.

Well, if we're going full-on depressing like that, I guess Camus's The Stranger is essential to anyone feeling on the outside of life. (Don't get me wrong, I love DFW, but IJ, like Camus, might be a bit... intense for delicate states of mind.)

There's a sci-fi bent in most of these answers, so I'll tack on with more Vonnegut: I'd probably pick Galapagos as the go-to book, there.

Some of the issues of conformity and the impact of a meaningful life in Ursula LeGuin's The Lathe of Heaven were also salient to me when I was young, though the precise reasons are slippery to my aging brain today.

If he's of a mischievous bent, Irvine Welsh (Trainspotting, Filth, Porno or the stories in The Acid House) can be pretty illuminating in a dark way.

More traditionally, Dostoyevsky's Notes from the Underground is a classic in the right mode, and I admire The World Famous's suggestion of Robinson Crusoe as an inspired idea. It really does take on completely different meanings for an adult reader.

If poetry's in play, there's really one obvious answer, and that's William Fucking Blake.
posted by rokusan at 12:27 PM on May 11, 2010

Microserfs by Douglas Coupland made me feel less... alone.
posted by ReiToei at 12:34 PM on May 11, 2010

Bird by Bird, by Anne Lamott. The subtitle says it all: "Some Instructions on Writing and Life." You don't need to be a writer to appreciate Lamott's words and find meaning in them.
posted by shallowcenter at 12:37 PM on May 11, 2010 [1 favorite]

I'm gonna second A Confederacy of Dunces by John Kennedy Toole. It's really one of my favorite books of all time.

I'd also look into some Borges. Complexity and ambiguity are good things to get acquainted with early on.

What's to Become of the Boy? Or, something to do with Books by Heinrich Boll is non-fiction about the author's high school years in Nazi Germany. He's a kid wrestling with questions of how he'll spend the rest of his life in the long-term, yes, but also how he and his family will continue to feed and shelter themselves today and tomorrow and live the way they see fit in the political climate of the time.

And, some Saul Bellow, FFS. The Adventures of Augie March is another favorite.

Also, The Educated Imagination by Northrop Frye is a nice little book of criticism on why we should read literature. I'm assuming he's something of a reader, so he may not need much convincing.

I'm not trying to convert anyone (I'm an atheist, myself), but I read certain books out of the King James Version of the Bible and was(am) taken by the beauty and simplicity of it.

"I returned and saw under the sun that the race is not to the swift; nor the battle to the strong; neither yet bread to the wise; nor yet riches to men of understanding; nor yet favour to men of skill; but time and chance happeneth to them all. For man also knoweth not his time; as the fishes that are taken in an evil net, and as the birds caught in the evil snare, so are the sons of men caught in an evil time when it falleth suddenly upon them."

(That's from Ecclesiastes, from memory, fools! Booo-ya!)

More than anything encouraging him to read widely is one of the best things you can do for him.

But, on the other hand, why not Ayn Rand? ;)
posted by honeybunny at 12:41 PM on May 11, 2010

Wow, some good ideas here. I had forgotten how much Going After Cacciatto had meant to me. (Tim O'Brien's books in general, too.)

I think it help to know more about him.
It would also help to know more about what you want him to get out of the books.
If he is looking for career direction, you might not want him to read any Ed Abbey. But I did it as a kid, it meant a lot to me and it made me make some life choices that, to this day, piss off my dad. I'd probably hand a kid The Brave Cowboy, Good News or Black Sun. I would argue loudly that he should not read The Monkey Wrench Gang. (That we he would, late at night and away from the house, thinking he was rebelling.) If he could give a fuck about being outdoors, I would leave Abbey out completely.

I think most Vonnegut is good because it shows how it is possible to be moral in an insane world. Career choices? Not really, but don't throw a book off the list because it doesn't answer the questions YOU think he is asking.

What does he already read? At that age, if you had handed me a non-fiction, what-are-you-going-to-do-with-your-life book, I would have used it for rolling paper. (I still probably would.) If it didn't have a story to catch my interest, I probably wouldn't have read it.

If he is already a reader, I do think Hesse can be good at that age. It can also backfire. I once spent two weeks alone in the woods alternating between mornings of heavy labor and afternoons of reading Hesse that left me a horribly twisted person. Luckily some good people took me in and made me forget my idiocy. Demian and Siddhartha can be a gateway to his books. Steppenwolf was almost unreadable for me until I had worked my way through every other book of his. That might have been because it was required reading.

Rereading the above, I realized that Good News is a post-apocalyptic novel. As a kid, I read a lot of those and had a deep attraction to them. Yeah, my anarchist little self wanted society to collapse, but I think the deeper attraction was the introspection required. Only in the extremes do we find out who we truly are. These probably aren't good for your boy, but I'll list the ones I have liked over the years, for future reference.
A Canticle for Liebowitz - Walter Miller
Earth Abides - George Stewart
Farnham's Freehold - Robert Heinlein (hey, I was a kid)
The Road - Cormac McCarthy (not sure this would have hit me so hard prior to the birth of my son, but it fits here in a way)
On the Beach - Nevil Shute
Alas, Babylon - Pat Frank
Z for Zachariah - Robert C. O'Brien
I think all of the post-Nuclear apocalypse in this list is really representative of the time I was growing up in.

I think I shall leave it there for now.
posted by Seamus at 12:47 PM on May 11, 2010

Along the lines of what Lemurrhea suggested, An Imperfect Offering, by James Orbinski, is excellent.

Judging by his biography, James Orbinski is superhuman. As a med student in the late '80s, he spent a year researching pediatric AIDS in Rwanda, which opened his eyes to the human consequences of political failure. After cofounding the Canadian chapter of Doctors Without Borders, Orbinski embarked on relief missions to the world's most chaotic pockets, including war-torn Somalia and the refugee camps of Afghanistan. When reports of genocide filtered out of Rwanda, Orbinski led a small team that--with scant supplies--tended to the sick and wounded in Kigali. Within 14 weeks, 800,000 people were killed as the international community sat idly by, and Orbinski experienced a profound personal crisis. He emerged with a renewed commitment to his role as doctor, not only as a healer but as a voice for those who have been disastrously failed by governments. In An Imperfect Offering, he bears witness to surreal levels of suffering, and his actions seem impossibly heroic. But descriptions of his patients' courage and his own moral challenges make this story an exploration of what it means to be human, and what our responsibilities are to each other. Through his story, the suffering of millions is no longer unimaginable, and indifference is not an option. --Mari Malcolm
posted by purlgurly at 12:53 PM on May 11, 2010

The Birth and Death of Meaning by Ernest Becker, but it's a lot to handle as a young adult.

I also remember being influenced by Outside the Dog Museum, specifically about the "sweetness of work and the undying hope of achievement."

They're both books I'd recommend to a slightly older Holden Caulfield, so might be worth a look.
posted by zueod at 12:59 PM on May 11, 2010

Perhaps I am unusual. I was far more influenced by:

Prometheus Rising - Robert Anton Wilson
Your Money or Your Life - Vicki Robin, Joe Dominguez, and Monique Tilford

Those books both challenge conventional approaches, and are bedrock to my adult opinions.

Online I would recommend one of my "shordupersavs" (short-duration-personal-saviors), Paul Graham:
He has a lot to say about risk taking (a good thing, especially for younger people) instead of career-ladder-climbing.

It wasn't out yet when I was a kid, but I unreservedly recommend "The Happiness Hypothesis" by Jonathan Haidt to anyone, kid or adult. Really excellent, and quite a bit different - it presents a distillation of research on what makes people happy instead of how not to be ill. Life changing, if you listen to its lessons.
posted by Invoke at 1:01 PM on May 11, 2010 [1 favorite]

Response by poster: Wow. Thanks for all the responses.

My son is not a veracious reader, but when he reads he appreciates good writing and responds especially well to emotional content. I’ve noticed him reading Vonnegut recently. So I’m looking for fiction or essay and I don’t think “tough” writers like Joyce or Wallace would work well (I love to read and it took me a two months to get through Infinite Jest, and everything of Joyce’s, but for Portrait, sits patiently on my to-do-someday list). I also think he would have a harder time appreciating classical authors, so I think I will stick with 20th Century authors.

Seamus -- you raise a good point. I love subversive writing but it might be a little strange coming from a parent. I’m not going to on the one hand try to discourage him from using too many drugs and on the other give him Castaneda’s books.
posted by rtimmel at 1:06 PM on May 11, 2010

To stick a few already-mentioned books together, Gilbert's Stumbling Upon Happiness could be paired nicely with Microserfs.

Pilgrim At Tinker Creek was probably the book that most influenced me at that age.
posted by Beardman at 1:11 PM on May 11, 2010 [1 favorite]

Films are literature, too. Be sure to rent "The Graduate" and "Harold and Maude." Also Rushmore-- the modern-day cousin of "The Graduate" which shows that these aren't just adolescent questions, they're kid questions and middle-aged questions-- human questions that we all deal with in some way.
posted by neitheror at 1:17 PM on May 11, 2010 [1 favorite]

In short order, I read Generation X, The Beautiful and the Damned, Bright Lights Big City, Less than Zero, Microserfs, and (reread) The Catcher in the Rye. They are all variations on the theme of alienation.
posted by plinth at 1:21 PM on May 11, 2010

T.H. White's "The Once and Future King" is a book that I've read every year for about 30 years now. I know chunks of it by heart, but there is always something new and something that resonates.
posted by pentagoet at 1:24 PM on May 11, 2010 [3 favorites]

his seem to relate more to direction and career

Ah, what does one do with one's life ~

At that age, I read a large proportion of those books mentioned above, and more.

They didn't answer the question. I left the books behind, and sought the answer in real life. I did many things in many places. Well, since I still do, I guess that didn't really answer the question either!


I recommend more worldly experience, either first-hand or second-hand, to balance out the interesting reading. What do people actually do at their jobs, how much do they get paid, how did they get there, do they like their work, what does it take to do the job well, etc. That's what young kids today tend to have no concept of. (Not their fault, either.)

By all means keep up the dialog with him. The world is very wide.
posted by coffeefilter at 1:31 PM on May 11, 2010

Someone mentioned it above, but I'll add an endorsement for Wallace Stegner's "Crossing to Safety."
posted by luazinha at 1:47 PM on May 11, 2010

Hm, well, On the Road got me through high school, however it does get a little old around 18. But he's about the age I was when I discovered Bukowski, who definitely opened my eyes a lot and made the world a lot bigger.

And definitely Vonnegut. Hell, I still re-read him when I'm feeling listless.

And Illusions was really awesome to read at 18 as well, even if it's a little... psuedo-whatever.

Infinite Jest? Guh.
posted by General Malaise at 1:48 PM on May 11, 2010

Walden of course, and biographies of people your son finds interesting could help kindle his inner flames.
posted by Pamelayne at 1:49 PM on May 11, 2010 [1 favorite]

This is hard. It's so easy to forget.

Annie Dillard and Barry Lopez both had a deep effect on me as a youth. (Dead on Beardman)
posted by Seamus at 1:51 PM on May 11, 2010

I read The Autobiography of a Yogi and a biography of Gandhi at an impressionable age, and they resonated for a long time.
posted by theora55 at 1:53 PM on May 11, 2010

Well, after high school I went on the deep and depressing train and read things like The Stranger, Being and Nothingness (and No Exit, the Flies). I mean - I recommend them and I don't. Depends on the kid. Could change his life for the better and give him deep insight and make him think about what his life could be, etc., or it could send him to the sad and maybe nutty house. hmmv.

Vonnegut is a damn good suggestion. As is Stranger in a Strange Land and Autobiography of a Yogi (a book I still haven't quite...uh...wrapped my head around? but definitely inspiring and interesting).

Thoreau is a great suggestion as well.

You could get him something like The Drunkard's Walk, so he'll know that his choices don't exactly matter and most of his life will be subject to random chance anyway. Again, like Sartre, might help, might hurt.

The reason Infinite Jest is a good suggestion is because it's at his age that people start down the path of monotonous career + boredom + substance abuse + passivity + all that other oh so American adult ennui/depression/hours of television thing. If he can manage to not jump on that path early, well, probably a good thing.
posted by Lutoslawski at 2:06 PM on May 11, 2010

I recommend The Wind-Up Bird Chronicle by Haruki Murakami. I read it during my sophomore year of college and it really knocked me flat. It's a surreal meditation on all kinds of things that he might be struggling with: careers and feeling adrift, relationships, communication, self-actualization, carving out meaning in an ambiguous world, getting outside of your own labyrinthine ego. The translation by Jay Rubin is clear and compulsively readable. Some find the book a bit difficult to parse, though I disagree; there are no easy answers, granted, but that's because easy answers to these questions don't exist.
posted by naju at 2:21 PM on May 11, 2010 [1 favorite]

Plus, my issues at his age were largely social, his seem to relate more to direction and career.

Growing Up Absurd by Paul Goodman

The sooner he comes to terms with what a shit situation we live in, the better, imo.
posted by mrgrimm at 2:30 PM on May 11, 2010

I have found The Little Prince to be consistently powerful at 8, 18, and 28...and hope to continue rediscovering it for all my decades to come.
posted by kitarra at 2:42 PM on May 11, 2010

I didn't think about the drug connections of Castaneda. On one of your hands, it did influence me to get in to psychedelia, on the other, the books eventually make it clear that the drugs are a crutch and the experiences pale next to the real thing.
posted by cmoj at 2:44 PM on May 11, 2010

I'll challenge the fiction request and recommend The Fabric of the Cosmos. I can't help but marvel at the strangeness of science, and although this is a book about theoretical physics, the author engages with the subject in a very approachable way and with a sense of wonder and curiosity.

Finding something that's constantly amazing to you is a big part what makes life worthwhile and meaningful. Science is one of those things that I find to fit the "amazing" criteria, but really, there are a lot of different areas that can be completely engaging to different people. I'd look for that sense of astonishment, instead of a particular sentiment or philosophy.

(The audio version is good for long road trips).
posted by _cave at 3:14 PM on May 11, 2010

I really got drawn into science fiction at that age and read Pournelle, Heinlein, too many others to count but the two authors that stood out the most for me are Brust and Gerrold.
In the same vein as Heinlein's Stranger in a Strange Land (which I never really liked) I did get a lot out of David Gerrolds books, specifically The War agaisnt the Chtorr. To me it is a more intelligent, enlightened Heinlein without the weird sexual stuff that came in to his later books. All his series are good, and really go into what a social contract means, the duty we have to ourselves and to society and the rights we possess, and what it may take to defend them. Plus wantign for the next chtorr book will help teach him patience (i keep wanting to write a letter to Gerrold just saying-get on with it in a monty python accent)

Brusts works are more fantasy than science fiction but are very character driven and you see the progression of a mans life through them. I am sure that there are many more books probably better written than these, but they are entertaining and really resonanted with me as a young man and I still enjoy reading and rereading most of the books by these two authors.
posted by bartonlong at 4:52 PM on May 11, 2010

I hit post too fast, Steven Brust is the author and he writes the Vlad Taltos and Drageara novels as well as several other stand alone titles
posted by bartonlong at 4:53 PM on May 11, 2010

Certainly try Catch-22. I read it at that age and it was influential.

It is similar to Vonnegut, is well-written yet easy to read, and has more than enough emotion and deep questions.

More importantly it can help a young person figure out how to be themselves in a challenging world, what to stand up for, what is worth going after, how to navigate social pressures, how to decide what is moral for yourself, etc.
posted by Solon and Thanks at 5:04 PM on May 11, 2010 [1 favorite]

The Outsiders, by Colin Wilson put me on to a whole new world of existential writing
posted by Pressed Rat at 5:09 PM on May 11, 2010

The Adventures of Huckleberry Finn. Seriously. I read it several times as a kid and loved it, but when I reread it for college I finally realized that the whole point of the book was not the adventure story on the raft but the moment when Huck says, "All right, then, I'll go to hell!"
posted by hydropsyche at 5:14 PM on May 11, 2010 [1 favorite]

18? Ordinary People by Judith Guest helped me get through a rough patch.

The Illuminatus Trilogy proceeded to blow my mind.
posted by clockbound at 5:31 PM on May 11, 2010

7 habits of highly effective people

Everything needed.
posted by chinabound at 5:53 PM on May 11, 2010

Invisible Man by Ralph Ellison. That book centers me like nothing else.
posted by yaymukund at 5:59 PM on May 11, 2010

seconding The Tao of Pooh - it's great
posted by 5_13_23_42_69_666 at 6:03 PM on May 11, 2010

For me it was Moon Palace by Paul Auster.
posted by Kattullus at 6:16 PM on May 11, 2010

More than anything else, The Dispossessed, by Ursula Le Guin - 6 years later I'm STILL thinking about it.

The poetry of Rumi - especially The Illuminated Rumi edited by Michael Green. Also many of Mary Oliver's poems.

The Great Gatsby -- no other book explains how painful shallowness can be as well.

The Poisonwood Bible, by Barbara Kingsolver, though I read that when I was 14.

There are an awful lot of others, feel free to message me if you'd like more suggestions though I suspect you have quite enough :)
posted by Cygnet at 6:21 PM on May 11, 2010

Gilles Deleuze and Felix Guattari - A Thousand Plateaus
posted by Joseph Gurl at 6:41 PM on May 11, 2010 [1 favorite]

I could diss Stranger in A Strange Land, because I found it rather annoying when I read it back in the old days.

Vonnegut is the absolute best inspirational writer, especially for those of us who don't heft tomes. He presents interesting philosophical questions in a engaging accessible way. Any book of his.

I could also favorite Dale Carnegie, and I regret that I have not enacted his advice more perfectly in my life.
posted by ovvl at 6:53 PM on May 11, 2010

Seconding the Illuminatus! trilogy. Lurid, terrible, and full of lots of attempts to make the reader start to notice the processes of their own thinking. Also there is sex.
posted by egypturnash at 6:57 PM on May 11, 2010

Asiapac books in Hong Kong produces a number of very good shorthand Chinese philosophy "comic books" in English. Each page is designed to tell a story in a few panels to illustrate a point. The books are very coherent. They cover Chinese Zen Buddhism, sure, but also Taoist and Confucian thought. See, teenagers struggle to answer big, unanswerable questions. The thing to realize is that there is not necessarily an "answer" or a "right" answer, and that you're better off concentrating on living as a righteous person instead.

I read them in high school and found that they clarified the mind wonderfully. Very accessible. They inspired me to study the real stuff later in life. I still have them today. Amazon sells some of their books.
posted by pandanom at 7:24 PM on May 11, 2010

Most of these books are terribly, terribly dry. I had trouble clearing the first 100 pages of the Illuminatus, even; bored the living hell out of me.

Honestly, I'd toss in Grant Morrison's series of graphic novels, the Invisibles. Stone Junction by Jim Dodge. Snow Crash by Neal Stevenson.

Work up to the dryer stuff, or there's almost no chance he won't find it utter shit.
posted by talldean at 7:33 PM on May 11, 2010

Specific books I loved when 18 (this was 1997): Catch 22, The World According to Garp. Geek Love. The Fuck Up. The Sandman graphic novels. Revolutionary Road. PS Your Cat Is Dead. Jitterbug Perfume. Even Cowgirls Get The Blues. Animal Farm. A Fine & Private Place. 1984. Stephen King. Vonnegut. Vonnegut. Vonnegut.

There's a lot of books people have listed that I think are fantastic reads now, but I wouldn't have had an iota of interest in at 18 (Infinate Jest, Murakami, Confederacy of Dunces). Either the materials would have been too dense or I just wasn't there yet, if you know what I mean. At 22+, yes, but not at 18. Your opinion may vary and all that.
posted by Windigo at 8:24 PM on May 11, 2010

I lived in Catch 22 through those years, read it more than a few times and loved it; Hellers characters are the best, he paints these people in words -- what a writer!

Twain, the essays and short stories he wrote toward the end of his life, after he'd lost so much that he held dear -- god-DAMN did he tell it like it was, he didn't pussy-foot around, told his truth as seen through his eyes. People say he'd become a cynic, embittered and angry and lost but I think they are full of shit, or, okay, maybe he was cynical, embittered, and angry but he goddamn sure wasn't lost; he knew what he wanted to say and said it well. I spent a lot of time in Huck Finn and it was good and good for me but I think the largest charge was from his later writing.
posted by dancestoblue at 8:41 PM on May 11, 2010

Oh, man! I can't believe I forgot the late, great Jim Carroll's Basketball Diaries and, even more strongly, Forced Entries. Not that I particularly aspired to becoming a heroin addict, but his amazing writing -- and very conscious dedication to his writing, even in his teens -- was incredibly inspiring to me.
posted by scody at 8:47 PM on May 11, 2010

I'm also a voracious reader and have been since I was a child. I agree with and have read most of the suggestions already listed, so I'm going to go on a bit of a tangent, maybe.

My Dad introduced me to Dune when I was 10. Frank Herbert book have their own philosophies built in. The Dune series, Whipping Star and The Dosadi Experiment. They also show different sociologies and different ways of thinking. Bonus for being fiction and relatively easy to read, especially at that age.

I handed my son Dune when he was 11, after he'd already seen both movie/miniseries versions. Told him, "whatever you don't understand now, you'll get more each time you re-read it." I plan on handing it to my girl this summer, when she's about the same age.

I may be in the minority here, but I really enjoy Tom Robbins' books. They're light enough to be fun, but with dashes of philosophy here and there. The leads are often wanna be artists who spend their days waitressing or whatever (this may be the biggest appeal for me, honestly, and I'm over 40).
posted by lilywing13 at 10:57 PM on May 11, 2010 [1 favorite]

Nthing Ishmael

Rules for Radicals by Saul Alinsky
posted by symbollocks at 5:12 AM on May 12, 2010

Shop Class as Soulcraft: An Inquiry Into the Value of Work is a great book that questions the value of liberal arts university degrees without shitting on them. Also explores the value of working with your hands, and wy it can be fulfilling and lead to high-paying jobs. Here is an essay by the author, which was later expanded into the book.
posted by Brodiggitty at 7:44 AM on May 12, 2010

At that age I was really into the Illuminatus trilogy, The Magus, Foucault's Pendulum (I read those three in a single weekend once-- that was a mind-bender), Jitterbug Perfume, and any conspiracy-esque kind of thing. I think I liked the idea that there was a "real" story behind the stories I was being told. As egypturnash says, though, this is just a sort of back-door into thinking about the ways in which we make meaning of things. I doubt I understood half of the stuff I read, but I powered through it. Partly just to feel like I was reading serious heavy stuff. I was kind of self-aggrandizing at that age - good thing I grew out of it. :)

What helped me the most emotionally, though, as a loner in a small town, was Eliot's "The Love Song of J Alfred Prufrock," and Cyrano de Bergerac (the Brian Hooker translation). I think you can't really go wrong reading either of those at any age.
posted by Pickman's Next Top Model at 10:04 AM on May 12, 2010

Most of these books are terribly, terribly dry. I had trouble clearing the first 100 pages of the Illuminatus, even; bored the living hell out of me.

Hm, I would say that about Ishmael, but not most of the other books.

I think the Illuminatus trilogy is a great selection for an 18-year-old. Foucault's Pendulum too is another page turner.

Stone Junction and Snow Crash are also great suggestions, though.

I also second The Book, or anything by Alan Watts. It might blow his mind a little.

(How about some Richard Brautigan? Hmm, maybe not ...)

Some that haven't been mentioned yet:

* The Last Temptation of Christ by Nikos K~ was fascinating to me at that age, but ymmv

* The Master and the Margarita (Bulgakov) is great for that age

* Tours of the Black Clock by Steve Erickson

* Brave New World (Huxley) seems mandatory in high school, but it's an excellent read.

* If he's already read BNW, Island provides a nice B-side

* George Orwell's Down and Out in Paris and London might be an interesting non-fiction read

* Valis, The Divine Invasion, and The Transmigration of Timothy Archer (Phil Dick)

* Sometimes a Great Notion (Ken Kesey)

* The Sunlight Dialogues by John Gardner

If he likes political philosophy at all, The Sunlight Dialogues is a fantastic read. It might be time for me to read it again ...

Also, you can never go wrong with Epictetus.
posted by mrgrimm at 12:04 PM on May 12, 2010

Agree with Catch-22. Maybe Fight Club. I really touted Power of One at that age, hopefully you don't watch the not-good-movie version. Consider Roots, or Rich Man, Poor Man. Oh! East of Eden was very good - it's about developing your own independent identity despite circumstances.
posted by jabberjaw at 12:13 PM on May 12, 2010

One Flew Over the Cuckoo's Nest by Ken Kesey

The Razor's Edge by Somerset Maugham

And, this might sound weird, but What Color Is Your Parachute? is oddly inspiring and offers really practical ways of finding passion and direction in one's life and career.

I was also really inspired by Possum Living as a teenager, as it showed me that there are so many other ways to live, economically and socially, than the way most kids are exposed to.
posted by Ouisch at 10:14 PM on May 12, 2010

I haven't read everything by Jane Jacobs, but I should. I found that The Death and Life of Great American Cities and Systems of Survival changed the way I saw the cities around me.
posted by Multicellular Exothermic at 7:25 PM on May 13, 2010

I read the Autobiography of a Yogi at 16/17. I also watched a movie about Mother Teresa around that time. Both of them left a lasting impression and form the basis of the person I am today.
posted by xm at 6:52 AM on May 14, 2010

Two mainstream (? Not sure if it's the word I want to use...) suggestions of books that changed my life in the last two years. I am currently 19, so right age range.

Eat, Pray, Love (more appropriate for a girl)
Life Of Pi
posted by iarerach at 8:21 PM on May 14, 2010

The Adventures of Augie March by Saul Bellow.
posted by Houyhnhnm at 6:47 PM on May 15, 2010

You write that your 18 year old son is struggling direction and career issues. I recommend the following books, not just because they're good books, but because I've found them helpful in working through some of these same challenges.

Because uncertainty is involved, I highly recommend a book by Jeff Bell called, "When in Doubt, Make Belief: An OCD-Inspired Approach to Living with Uncertainty." Jeff Bell is diagnosed as having OCD, but his book is for anyone struggling with issues of direction and the uncertainty of making a choice. Growing up an 18 year old in this world is most definitely an uncertain place, and this book references many of the outstanding books listed above into a tight synthesis with guidance about how to apply it. The conclusion of the book contains interviews with highly successful people including Leon Panetta and a West Point veteran of Afghanistan. At the heart of this book is a commitment both to a belief that we live in a good universe and that we commit to our higher calling within that universe. It might be helpful in considering direction and career.

As meditations about calling and vocation, I highly recommend Stephen King's Dark Tower series (7 books in total). It is Stephen King's master opus, written over a span of some 20 years. I found the central theme of this immersive world to be what we are called to be, what talent there is inside of us that yearns to be used. As a word of caution, central characters in these books are known as "gunslingers," though I think the level of violence in this book is considerably less than most of the gunk that's on television today and certainly applied with much more restraint. Alternately, I recommend the Hatrack River series (Tales of Alvin Maker) by Orson Scott Card. Like Stephen King's Dark Tower series, this is basically a series about finding that thing inside us that we innately do as easily as breathing. It's about committing to putting whatever ability this may be to use for the betterment of the people around us.

Finally, I echo recommendations for Kurt Vonnegut, especially "Cat's Cradle" with a central idea that it is impossible to make mistakes and that life is a little ridiculous anyway. "Free Play: Improvisation in Life and Art" by Stephen Nachmanovitch also relates to this idea about not being afraid to make mistakes. Along the same lines, Kahlil Gibran's "The Prophet" is also outstanding as a meditation about life in general.
posted by SocialArgonaut at 4:54 PM on May 18, 2010

You may not like Ayn Rand but that doesn't mean you should disclude it from your son's reading. I read it at a similar age and it had a huge impact on me and helped me clarify what i wanted to be doing in my life - much moreso than slaughterhouse 5 (an enjoyable read nonetheless). Maybe it will have a similar impact on him, maybe it won't but by offering it, at least you've given him the choice.
posted by parryb at 2:35 PM on May 29, 2010

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