Here’s the problem with reading the books that everyone else has read. It makes you more like everyone else. Checking off the various books from your high school curriculum, and then, perhaps the “100 Greatest Books Ever Written” is the educational equivalent of skating to where the puck is and not where it’s going.

Reading is about insight into the human experience, about understanding. What does following in the footsteps of everyone else get you? It gets you to exactly the same conclusions as everyone else.

Not to say that the books in our “canon” aren’t valuable, because they certainly are. It’s just that you have to remember for every Great Gatsby out there, there were 10 others written at the same time about the same thing that for whatever twist of cultural fate and cumulative advantage are mostly lost to us (one of the books on this list fits that definition to a T).

The Western world has been publishing books for some 3,000 years. Memoirs, histories, aphorisms, essays, treatises, tutorials, exposes, stories, epics–it’s all there. Humble yourself to think that our grasp of the lists of the “best” of these books will always miss more than it captures.

Which is why I put together the list of books below in their rough historical order. They are all great pieces of literature or learning and at the same time, mostly unknown. Sure, you might have heard of a few of them (in which case, consider yourself part of the minority) but far too many people haven’t. Put down your David Foster Wallace and pick up one of these. See what happens.

Cyropaedia (a more accessible translation can be found in Xenophon’s Cyrus The Great: The Arts of Leadership and War)
Xenophon, like Plato, was a student of Socrates. For whatever reason, his work is not nearly as famous, even though it is far more applicable. Unlike Plato, Xenophon studied people. His greatest book is about the latter, it’s the best biography written of Cyrus the Great (aka the father of human rights). There are so many great lessons in here and I wish more people would read it. Machiavelli learned them, as this book inspired The Prince.

The Moral Sayings of Publius Syrus: A Roman Slave by Publius Syrus
The best philosophy comes from people who were not “philosophers.” Syrus was a slave and his moral maxims are far better than perhaps the most famous book in this category, those of Duc de la Rochefoucauld. Some favorites: “The mightiest rivers are easy to cross at their source.” “Avarice is the source of its owns sorrows.” And of course, extra-applicable to this list, “Many receive advice, few profit by it.”

Meditations by Marcus Aurelius (Gregory Hays translation, do not read the others, they suck)
Those familiar with my writing will not think this is an unknown book. But for far too many people it is. You can get a PhD in philosophy and not be forced to read this–and that’s a travesty. I imagine because it’s one of the few texts that wastes no time on pretension or explanations of the world. It simply tells you how to live a little better. Just wrap your head around this: At some point around 170 AD, the single most powerful man in the world sat down and wrote a private book of lessons and admonishments to himself for becoming a better, kinder and humbler person. And this text survives and you have access to it today.

The Lives of the Most Excellent Painters, Sculptors, and Architects by Giorgio Vasari
Basically a friend and peer of Michelangelo, Da Vinci, Raphael Titian and all the other great minds of the Renaissance sat down in 1550 and wrote biographical sketches of the people he knew or had influenced him. Unless you have a degree in Art History it’s unlikely that anyone pushed this book at you and that’s a shame. Because these great men were not just artist, they were masters of the political and social worlds they lived in. There are so many great lessons about craft and psychology within this book. The best part? It was written by someone who actually knew what he was talking about, not some art snob or critic, but an actual artist and architect of equal stature to the people he was documenting.

The Man Without a Country by Edward E. Hale
Patriotism is not a concept that gets a lot of love today. But this essay/book makes you think a little. Released in 1863 during the height of the Civil War, the plot’s simple: an innocent man caught up in Aaron Burr’s treasonous conspiracy stands trial for his actions. When asked to address the judge, he bitterly remarks that he wishes to be done with the United States forever. So the judge grants his wish as a punishment–he’s sentenced to live the rest of his life in a cabin aboard ships in the US Navy’s foreign fleet, and no sailor is to ever mention the US to him again. He dies many years later, an old man like Rip Van Winkle, unsure of the changing world around him. For those with some understanding of historical, you’ll enjoy the meta-fiction of it, for those that haven’t it is still a very good look into early America.

12 Years A Slave by Solomon Northup
This one won’t stay unknown for long as Brad Pitt’s doing a movie about it but please don’t let that scare you away. If there is one book you read about slavery in America, read this one. It’s the real story of a born freedman in the North who, as a traveling musician, was brought out of his home state on false pretenses in order to be captured, kidnapped, and transported South to be sold as a slave. It’s fucking harrowing and written lucidly and articulately by the person who experienced it. For 12 years, he was a slave–and not some border-state slave, but a bayou slave in the deep South. He was cut off from his family and his freedom, and even among the slaves he was different. He couldn’t tell anyone he could read and write, he couldn’t even tell anyone that he was formerly free because they threatened to kill him if he did. This book is just as good as Frederick Douglass’ memoir and I think illustrates the horrors of slavery in a much more undeniable way.

Civil War Stories by Ambrose Bierce
Mark Twain, for all his bitterness and sarcasm, was just more fun for average people to read than Ambrose Bierce. But Bierce is the one who truly captured the Civil War–a terrible and awful conflict in which death and destruction and stupidity were far more prevalent than strategy or heroism. This book (half fiction and half memoir) contains the story “An Occurrence at Owl Creek Bridge,” which Kurt Vonnegut called the greatest short story ever written. Too many books about the Civil War are inaccessible, with their flanking movements and war vocabulary. This book is all people. Must read.

Forty Years a Gambler on the Mississippi by George Devol
The memoir of a professional gambler, fighter and criminal who rode the riverboats of the Mississippi and Red Rivers. It’s a true and vibrant snapshot of a period of American life that you can’t get anywhere else. Gun fights, brawls, cons–it’s all here. Fascinating, peculiar and very easy to read.

Hunger by Knut Hamsun
A dark and moving first-person narrative, about the conflicting drives for self-preservation and self-immolation inside all of us. Hunger is about a writer who is starving himself. He cannot write because he is starving and cannot eat because writing is how he makes his living. It’s a vicious cycle and the book is a first-person descent into it. Strangely modern for being published in 1890 and ultimately inspired a lot of great stream-of-consciousness writing since (but influence goes unacknowledged because Knut was a Nazi sympathizer).

Letters from a Self-Made Merchant to His Son by George Horace Lorimer
This book is the preserved correspondence between Old Gorgon Graham, a self-made millionaire in Chicago, and his son who is coming of age and entering the family business. The letters date back to the 1890s but feel like they could have been written in any era. Honest. Genuine. Packed with good advice.

My Life and Battles by Jack Johnson
This is the lost and translated book that came out of a series of pieces Johnson–perhaps the greatest boxer who ever lived–wrote for a French newspaper in 1911. It’s not very long but it is full of really interesting strategies and anecdotes. You get the sense that he was an incredibly intelligent and sensitive man–clearly had a thirst for drama and attention. Who knows what place he would occupy in our culture and history had he not been taken down so thoroughly by racism and genuinely evil people? But despite all that, he was always smiling. As Jack London put it after Johnson’s most famous fight: “No one understands him, this man who smiles. Well, the story of the fight is the story of a smile. If ever a man won by nothing more fatiguing than a smile, Johnson won today.”

Company K by William March
Far and away the best book ever written about WWI. Better than All Quiet on the Western Front or Goodbye to All That or any of the other classics. But that’s the problem–WWI was awful, perhaps the most awful thing of the 20th century. And this book is forgotten precisely because it portrays the war and its pointlessness too realistically. We want to know, but we don’t really want to know.

Babbitt by Sinclair Lewis
I don’t think there was anyone in the 1920s who would have believed that this book would be completely forgotten. By all accounts, it was destined to be a classic critical novel of the American Dream. You can’t read anything about the ’20s and ’30s that doesn’t comment on Babbitt (sold 130,000 copies its first year, HL Mencken loved it, it won Lewis a Nobel Prize). Calling someone a “Babbitt” was considered an insult and the phrase became a constant topic of conversation in the media and literature. Yet, here we are 80-90 years later: you’ve probably never heard of the term or the book. Perhaps it’s because the biting satire of American suburban middle class life cuts deeper now than it did then. It doesn’t matter if the book is old, it’s still very funny and at its core, a critique of conformity and what Thoreau called the “life of quiet desperation.”

Asylum: An Alcoholic Takes the Cure by William Seabrook
In 1934, William Seabrook was one of the most famous journalists in the world. He was also an alcoholic. But there was no treatment for his disease. So he checked himself into an insane asylum. There, from the perspective of a travel writer, he described his own journey through this strange and foreign place. Today, you can’t read a page in the book without seeing him bump, unknowingly, into the basic principles of 12-step groups and then thwarted by well meaning doctors (like the one who decides he’s cured and can start drinking again). On a regular basis, he says things so clear, so self-aware that you’re stunned an addict could have written it–shocked that this book isn’t a classic American text. Yet all his books are out of print and hard to find. Two of my copies are first editions from 1931 and 1942. It breaks your heart to know that just a few years or decades later, his options (and outcome) would have been so very different (he eventually died of an opium overdose).

Ask the Dust by John Fante
This is the west coast’s Great Gatsby. Fante has benefited from some recognition–mostly thanks to Bukowski championing him in his later years–but because the book is about Los Angeles and not New York City, it is mostly forgotten. Better than Gatsby, it is a series. Bandini, the subject of the series, is a wonderful example of someone whose actual life is ruined by the fantasies in his head–every second he spends stuck up there is one he wastes and spoils in real life. He’s too caught up and delusional to see that his problems are his fault, that he’s vicious because he can’t live up to the impossible expectations they create, and that he could have everything he wants if he calmed down and lived in reality for a second. This is the series in order by my favorites: Ask the Dusk, Dreams from Bunker Hill, Wait Until Spring, Bandini and The Road to Los Angeles. (DO NOT watch the movie version of Ask to Dust, it is embarrassingly bad.)

Why Don’t We Learn from History? and Strategy by BH Liddell Hart
These are two very short books but will help you understand the topics more than thousands of pages on the same topic by countless other writers. In my view, Hart is unquestionably the best writer on military strategy and history. Better than von Clausewitz, that’s for sure (who for all the talk is basically useless unless you are planning on fighting Napoleon). His theories on the indirect approach is life changing, whether you’re struggling with a business or just office politics. I can’t say much more than read these books. It’s a must.

The Crack Up by F. Scott Fitzgerald
If you like Asylum, read The Crack Up, a book put together by Fitzgerald’s friend Edmund Wilson after his death. It is such an honest and self-aware compilation of someone hell-bent on their own destruction. At the same time, Fitzgerald’s notes and story ideas within the book make it undeniably clear what a genius he truly was. It’s a sad and moving but necessary read.

On the Rock: Twenty Five Years in Alcatraz by Alvin Karpis
John Dillinger was played by Johnny Depp. Most people know who he was–mostly because he died in a hail of bullets. But they forget that the other Public Enemy #1 at the time was Alvin Karpis and he didn’t die. In fact, he lived up until the 1980s. Just enough time to do a couple decades at Alcatraz with guys like Al Capone. During a temporary transfer to an alternate prison, Karpis met a young weirdo named Charlie Manson and taught him how to play guitar.

Death Be Not Proud by John Gunther
Written in 1949 by the famous journalist John Gunther about his death of his son–a genius–at 17 from a brain tumor, this book is deeply moving and profound. Every young person will be awed by this young boy who knows he will die too soon and struggles to do it with dignity and purpose. Midway through the book, Johnny writes what he calls the Unbeliever’s Prayer. It’s good enough to be from Epictetus or Montaigne–and he was fucking 16 when he wrote it. It’s reading the book for that alone.

The Harder They Fall by Budd Schulberg
Budd Schulberg’s (who wrote On the Waterfront) whole trilogy is amazing and each captures a different historical era. His first, What Makes Sammy Run? is Ari Gold before Ari Gold existed–purportedly based on Samuel Goldwyn (of MGM) and Daryl Zanuck. His next book, The Harder They Fall is about boxing and loosely based on the Primo Carnera scandal. His final, The Disenchanted is about Schulberg’s real experience being attached to write a screenplay with a dying F. Scott Fitzgerald. All you need to know about Schulberg’s writing is captured in this quote from his obituary: “It’s the writer’s responsibility to stand up against that power. The writers are really almost the only ones, except for very honest politicians, who can make any dent on that system. I tried to do that. And that’s affected me my whole life.”

Losing the War by Lee Sandlin
This is an essay, not a book, but if you have to read one thing about WWII, this is it. Sandlin is a master and the essay is free, read it.

The Measure of My Days by Florida Scott Maxwell
The daily notes of a strong but dying woman (born 1883, written in 1968) watching her life slowly leave her and wind to a close. The wisdom in this thing is amazing and the fact that most people have no idea exists–and basically wait until the end of their life to start thinking about all this is very sad to me. Also I love her generation–alive during the time of Wyatt Earp yet lived to see man land on the moon. What an insane period of history.

The Power Tactics of Jesus Christ and Other Essays by Jay Haley
The title essay in this book is peerless and amazing. The rest of the essays, which talk about Haley’s unusual approach to psychotherapy are also quite good. If you’ve gone to therapy, are thinking about going to therapy, or know someone going to therapy, this book is a must-read.

The Tiger: A True Story of Vengeance and Survival by John Vaillant
I’ll end with this book because it’s the most recent. The (true) story is simple: man in Siberia wounds tiger while hunting to feed his family. Tiger goes on killing spree while hunting the man down, and is stopped only when the Russian government dispatches a special SWAT team to track and kill it. This is probably the single best piece of nonfiction journalism I’ve ever read. I suppose it’s not totally unknown but I’m guessing you haven’t read it and that needs to change, now.

I’ve tried to capture most of the major eras and epochs above, from classical Greece to the Renaissance to the great wars of the 20th century. Yes, it is heavy on American history. But guess where most of the people reading this live?

Like I said, there are certain classic texts that we must read–books that have become cultural rites of passage. No one is saying you should skip your high school reading list. The problem is thinking that that’s enough. In order to work for “everyone,” those books had to be safe, they had to be accessible, they had to be provocative but not too provocative. There is a very understandable reason that we read All Quiet on the Western Front and not Company K. Or that we read Huckleberry Finn to understand slavery and not Solomon Northup’s real memoir.

Because the latter books are real. The others keep us comfortable, even when they make us think.

The next step is digging a little bit beneath the surface, leaving the road and exploring parallel or divergent paths. I hope some of these books do that for you. They certainly did for me.

This post originally ran on Comments can be seen there.

Everyone knows that reading is important, and most of us wish we did more of it. I understand that I am supremely lucky to have as much time to do it as I do. For that reason, at the end of each year, I try to narrow the hundreds of recommendations from my reading list down to just the very, very best. If you have to be selective with your time or money, these are the ones I promise are worth the time and investment. If you really like them and want more like it, the rest of the emails start with the Best Of 2011 and 2012 and stay tuned for January’s recommendations.

Average Is Over: Powering America Beyond the Age of the Great Stagnation by Tyler Cowen
This was the most important book I read this year. It’s the only one I framed a passage from to put on my wall. It was the only one I thought was so good I bought for multiple other people this year (it also inspired the one piece of writing I am most proud of this year). Cowen’s books have always been thought provoking, but this one changes how you see the future and help explain real pain points in our new economy–both good and bad. Although much of what Cowen proposes will be uncomfortable, he has a tone that borders on cheerful. I think that’s what makes this so convincing and so eye opening. A hollowing out is coming and you’ve got to prepare yourself (and our institutions) as best you can. To me, this book belongs along side other econo/social classics like Brave New War, Bowling Alone and The Black Swan. As a good extension of the themes in this book, I also recommend Plutocrats by Chrystia Freeland.

All the Great Prizes: The Life of John Hay, from Lincoln to Roosevelt by John Taliaferro
It’s hard for me to recommend just one great biography this year, so I won’t even try. I’ll just start with this biography of John Hay, which was my favorite–though there were many close seconds. John Hay started as a teenage legal assistant in the law office of Abraham Lincoln. He ended his career as the Secretary of State for William McKinley and Theodore Roosevelt. How nuts is that? You can basically understand the entire period of American history from the Civil War through WWI through one man who saw it all. Great biography of politics, the press, and American society. I also strongly recommend Eisenhower in War and Peace by Jean Edward Smith–I did not fully appreciate what a strategic and political genius Eisenhower was until this book. Jon Krakauer’s biography of Pat Tillman, Where Men Win Glory, was the most inspiring and moving book I read this year. Tom Reiss’s book The Black Count was impressive and a side of French history I never knew and never would have otherwise. You cannot go wrong with any of these biographies.

The Aneiad by Virgil (translated by Robert Fagles)
I made an effort to read some classical poets and playwrights this year. The Aneiad was far and away the most quotable, readable and memorable of all of them. There’s no other way to put: the story is AMAZING. Better than the Odyssey, better than Juvenal’s Satires. Inspiring, beautiful, exciting, and eminently readable, I loved this. I took more notes on it that I have on anything I’ve read in a long time. The story, for those of you who don’t know, is about the founding of Rome. Aeneas, a prince of Troy, escapes the city after the Trojan War and spends nearly a decade wandering, fighting, and trying to fulfill his destiny by making it to Italy. I definitely recommend that anyone trying to read this follow my tricks for reading books abve your level (that is, spoil the ending, read the intro, study Wikipedia and Amazon reviews, etc). I also enjoyed Euripides and Aeschylus this year and I hope you will too.

I can’t help myself. Some other honorable mentions:
Company K by William March (if you read one book about WWI, or one book of fiction about war, pick this one)
Eleven Rings: The Soul of Success by Phil Jackson (favorite business or leadership book in a long time)
Shadow Divers: The True Adventure of Two Americans Who Risked Everything to Solve One of the Last Mysteries of WWII by Robert Kurson (goddamn this guy can tell a story)
The River of Doubt and Destiny of the Republic by Candice Millard (these two unusual historical narratives about U.S presidents are shockingly good. I will read whatever else this woman writes)

For more great recommendations in 2014, sign up and stay tuned. If anyone has any gems to recommend, please send them my way. If you’re looking for marketing books, Trust Me I’m Lying came out in a revised and expanded edition this year and Growth Hacker Marketing is out now in ebook and audio and will be released in paperback in Sept 2014.

What is Scarce?

December 16, 2013 — 12 Comments

To put the question in the bluntest possible way, let’s say that machine intelligence helps us make a lot more things more cheaply, as indeed it is doing. Where will most of the benefits go? In accord with economic reasoning, they will go to that which is scarce.

In today’s global economy here is what is scarce:

1. Quality land and natural resources

2. Intellectual property, or good ideas about what should be produced.

3. Quality labor with unique skills

Here is what is not scarce these days:

1. Unskilled labor, as more countries join the global economy

2. Money in the bank or held in government securities, which you can think of as simple capital, not attached to any special ownership rights (we know there is a lot of it because it has been earning zero or negative real rates of return)

Tyler Cowen, Average is Over

This is now framed and on my wall.

“One has to kill a few of one’s natural selves to let the rest grow — a very painful slaughter of innocents.” – Henry Sidwick.

You, the ambitious young person, how many of your natural selves have you identified yet? How many of them are suffocating? Are you prepared for the collateral damage that’s going to come along with letting the best version of you out?

My victims:

Ryan, college student 1 year from graduating with honors
Ryan, the Hollywood executive and wunderkind
Ryan, director of marketing for American Apparel

All dead before 25. May they rest in pieces.

I am a perpetual drop out, quitting, abandoning or changing paths just as many others in my position would be getting comfortable. By Sidwick’s terms, I guess I am a serial killer. This “slaughter” made room for the exponential growth of Ryan Holiday, published author. But he better not get comfortable either. Because he too may have to be killed one day. And that will be a good thing.

Because the future belongs to those who have the guts to pull the trigger. Who can drop out and fend for themselves. If you’re reading this site, you might already be contemplating a decision like that. I want to show you why it might be the right call for you and how to do it.

The Big Myth

“It wasn’t quite a choice, it was a realization. I was 28 and I had a job as a market researcher. One day I told my psychiatrist that what I really wanted to do was quit my job and just write poetry. And the psychiatrist said, ‘Why not?’ And I said, ‘What would the American Psychoanalytic Association say?’ And he said, ‘There’s no party line.’” – Allen Ginsberg

Let’s get the big myth out of the way. There’s not much dropping involved in dropping out of school. When I did it, I remember walking to the registrar’s office — I was so nervous. My parents had disowned me, I needed to move to a new city, the girl whose job I stole hated me. Why was I doing it? I’d just helped sign my first multi-platinum rock act and I wasn’t about to go back to the dorms and tolerate reading in the newspaper about other people doing my work. I was 20 years old.

I’m here to drop out of school, I announced to the registrar (like I was some presidential candidate who thinks he literally has to throw his hat into a ring). In fact, as my advisor informed me, that wasn’t exactly necessary. I could take a leave of absence for up to a year and possibly more, without even jeopardizing my scholarship. I braced for the same condescending, paternalistic lecture I’d gotten from my parents. It didn’t come. These people were happy for me. And if I submitted the right forms, I might even be able to get course credit for the work. How’s that for a party line?

So I took the plunge, and like many big risks, it turned out that dropping out of school was more manageable than I could have ever anticipated.

What I Wish I’d Known

I get a lot of emails from kids who are on the verge of dropping out. They always seem so scared. And I empathize with them. I know I was scared when I quit. Even billionaires, years removed from the decision that has now, in their case, been clearly vindicated, still speak of the hesitation they felt when they left school. Were they doing the right thing? What would happen? Were they throwing everything away?

It’s the scariest and most important decision most young entrepreneurs, writers, artists will ever make. So naturally, they take it very seriously. But doing that — taking it so seriously — almost wrecked me.

I remember pulling into a parking space one day a few months after dropping out, stressed and on the verge of a breakdown. Why am I killing myself over this?, I thought. It’s just life. Suddenly, a wave of calm washed over me. I was doing what young people are supposed to do: take risks. There is no need to stress over anything so seriously, let alone school (as someone told me later, he’d gotten sick when he was in college and missed 18 months of school. He’s 50 now and a year and half seems like two seconds). I’m not going to starve. I’m not going to die. There is nothing that can’t be undone. Just relax. Relax. And I did. And it worked.

If I’d realized it sooner, I could have avoided many needlessly sleepless nights.

I also wish someone had given me some more practical advice:

  • Try to have a few months money on hand. It makes you feel less pressure and gives you more power in negotiating situations.
  • Keep a strong network of friends — college friends especially. The unusualness of your situation is a warping pressure.
  • Keep connected to normal people so you can stay normal.
  • Take notes! I wish I’d written down my observations and lessons for myself the first time I dropped because it wasn’t my last time and I could prepared better for round II and III.

Why I Did It Again (and again)

When I dropped out of school, I was betting on myself. It was a good bet (one that surprised me, honestly). In less than 3 years, I’d worked as a Hollywood executive, researched for and promoted multiple NYT bestsellers, and was Director of Marketing for one of the most provocative companies on the planet. I had achieved more than I ever could have dreamed of — the scared, overwhelmed me of 19 could have never conceived of having done all that. (Which is why I killed that younger version of me). Yet, I knew it was time to drop out again. The six-figure job had to go. It was time for the next phase in my life. What I had, just like college had been, was holding me back.

That’s exactly what I did. I left and moved 2,000 miles away to write a bookIt was wracking and risky and hard for everyone in my life to understand. But I was prepared this time. I knew what to expect. I’d saved my money, I built up my support system and I refused to take it too seriously. Whatever happened, I probably wouldn’t die.

…and I didn’t. In fact, within six months I’d sold the book to Penguin for several times my previous salary and was securely on my new path.

Welcome to the Future

I, and the many people who email me, seem to have a funny habit: We repeatedly leave and give up the things that most people work so hard to achieve. Good schools. Scholarships. Traditional jobs. Money. We don’t believe in sunk costs. If that sounds like you, then you’re probably a perpetual drop out too. Embrace it. I have.

I know that I will do it again and again in my life. Why? Because every time I do, things get better. The trial by fire works. It’s the future. The institutions we have built to prop us up seem mostly to hold creative and forward thinking people back. College is great, but it is slow and routine. Corporations can do great things, but fulfilling individuals is not one of them. Money is important but it can also be an addiction. Accomplishments like a degree or a job are not an end, they are means to an end. I’m so glad I learned that.

On your own path in life, remember the wise words of Napoleon and “Trade space for time.” (Or if you prefer the lyrics of Spoon “You will never back up an inch ever/that’s why you will not survive.”) Space is recoverable. The status of a college degree, the income from a job — recoverable. Time is not. This time you have now is it. You will not get it back. If you are stuck in a dorm room or wedged into a cubicle and what you are doing outside of those places is actually the greatest possible use of you, then it’s time to drop out.

Acknowledge, as Marcus Aurelius writes, the power inside you and learn to worship it sincerely. It may seem counter-intuitive that dropping out — quitting — is part of that, but it is. It’s faith in yourself. It’s about not needing a piece of paper or other people’s validation to know you have what it takes and are worth betting on. This is your life, I hope you take control and get everything you can out of it.

This post originally ran on Thought Comments can be seen there. I also recommend this post 15 Reasons Why You Should Drop Out of College.

Why are you traveling?

Because, you know, you don’t magically get a prize at the end of your life for having been to the most places. There is nothing inherently valuable in travel, no matter how hard the true believers try to convince us.

Seneca, the stoic philosopher, has a great line about the restlessness of those who seem compelled to travel. They go from resort to resort and climate to climate, he says. “They make one journey after another and change spectacle for spectacle. As Lucretius says, “Thus each man flees himself. But to what end if he does not escape himself? He pursues and dogs himself as his own most tedious companion. And so we must realize that our difficulty is not the fault of the places but of ourselves.”

It’s hard for me to see anything to envy in most people who travel. Because deep down that is what they are doing. Fleeing themselves and the lives they’ve created. Or worse, they’re telling themselves that they’re after self-discovery, exploration or perspective when really they are running towards distraction and self-indulgence.

Is that why you’re packing up your things and hitting the road?

Are you, as Emerson once put it, “bringing ruins to the ruins?”

The purpose of travel, like all important experiences, is to improve yourself and your life. It’s just as likely — in some cases more likely — that you will do that closer to home and not further.

So what I think about when I travel is that “why.” (Some example “whys” for me: research, to unplug, to go straight to the source of something that is important to me or I need to see in person, a job or a paying gig, to show something that’s important to me to someone who is important to me, etc etc) I don’t take it as self-evident that going to this place or that place is some accomplishment. There are just as many idiots living in Rome as there are at home.

And when you make this distinction most of the other travel advice falls away. The penny pinching and the optimization, the trying to squeeze as many landmarks into a single day, all that becomes pointless and you focus on what matters.

So what I am saying is that saving your money, plotting your time off work or school, diligently tracking your frequent flyer miles and taking a hostel tour of Europe or Asia on budget is the wrong way to think about it.

In the vein of my somewhat controversial advice for young people, I thought I’d give some of my thoughts not just on traveling but on how to do it right.

My Travel Rules and Criteria

[*] Instead of doing a TON of stuff. Pick one or two things, read all about those things and then actually spend time doing them. Research shows that you’ll enjoy an experience more if you’ve put effort and time into bringing it about. So I’d rather visit two or three sights that I’ve done my reading on and truly comprehend than I would seeing a ton of stuff that goes right in and out of my brain. (And never feel “obligated” to see the things everyone says you have to).

[*] Take long walks.

[*] What are you taking all these pictures for? Oh for the memories? So just look at it and remember it. Experience the present moment.

[*] Read books, lots of books. You’re finally in a place where no one can interrupt you or call you into meetings and since half the television stations will be in another language…use it as a chance to do a lot of reading.

[*] Eat healthy. Enjoy the cuisine for sure, but you’ll enjoy the place less if you feel like a fucking slob the whole time. (To put it another way, why are you eating pretzels on the airplane?)

[*] Try to avoid guidebooks, which are superficial at best and completely wrong at worst. I’ve had a lot more luck pulling up Wikipedia, and looking at the list of National (or World) Historical Register list for that city and swinging by a few of them. Better yet, I’ve found a lot cooler stuff in non-fiction books and literature that mentioned the cool stuff in passing. Then you google it and find out where it is.

[*] I like to go and stand on hallowed ground. It’s humbling and makes you a better person. Try it.

[*] Come up with a schedule that works for you. Me, I get up in the morning early and run. Then I work for a few hours. Then I roll lunch and activities into a 3-4 hour block where I am away from work and exploring the city I’m staying in. Then I come back, work, get caught up, relax and then eventually head out for a late dinner. In almost every time zone I’ve been in, this seems to be the ideal schedule to A) enjoy my life B) Not actually count as “taking time off.” No one notices I am missing. And it lets me extend trips without feeling stressed or needing to rush home.

[*] Don’t check luggage. If you’re bringing that much stuff with you, you’re doing something wrong.

[*] When you’re traveling to a new city, the first thing you should do when you get to the hotel is change into your workout clothes and go for a long run. You get to see the sights, get a sense of the layout and then you won’t waste an hour of your life in a lame hotel gym either.

[*] Never recline your seat on an airplane. Yes, it gives you more room — but ultimately at the expense of someone else. In economics, they call this an externality. It’s bad. Don’t do it.

[*] Stay in weird ass hotels. Sometimes they can suck but the story is usually worth it. A few favorites: A hotel that was actually a early 20th-century luxury train car, a castle in Germany, the room where Gram Parsons died in Palm Desert, a hotel in Arizona where John Dillinger was arrested, a hotel built by Wild Bill Hickok, etc etc.

[*] Add some work component to your travel if you can. Then you can write it all off on your taxes.

[*] Don’t waste time and space packing things you MIGHT need but could conceivably buy there. Remember, it costs money (time, energy, patience) to carry pointless things around. (Also, most hotels will give you razors, toothbrushes, toothpaste and other toiletries).

[*] Go see weird shit.

[*] Ignore the temptation to a) talk and tell everyone about your upcoming trip b) spend months and months planning. Just go. Get comfortable with travel being an ordinary experience in your life and you’ll do it more. Make it some enormous event and you’re liable to confuse getting on a plane as an accomplishment by itself.

[*] In terms of museums — I like Tyler Cowen’s trick about pretending you’re a thief who is casing the joint. It changes how you perceive and remember the art. Try it.

[*] Don’t upgrade your phone plan to international when you leave the country. Not because it saves money but because it’s a really good excuse to not use your cellphone for a while. (And if you need to call someone, try Google Voice. It’s free).

[*] You know there are lots of cool places inside the United States. The South is beautiful and chances are you haven’t seen most of it. There’s all sorts of weird history and ridiculous things that your teachers never told you about. Check it out, a lot of it is within a day or two drive.

In other words…

Travel should not be an escape. It should be part of your life, no better or no worse than the rest of your life. If you are so dissatisfied with what you do or where you live that you look forward to NOT being and spend weeks and months figuring out how to get a few days off from it, that should be a wake up call. There’s a big difference between wanting a change in scenery and some new experiences vs. needing to run away from a prison of your own making.

There is to me, a lot more to admire in someone who stayed put and challenged their perspectives and habits and lifestyle choices at home than there is to some first world Instagram addict who conflates meaning with checking off boxes on a bucket list.

So ask: Do you deserve this trip? Ask yourself that honestly. Am I actually in a place to get something out of this?

Over the years, I feel like I have mastered the art of something I wouldn’t call travel. I’d call it living my life in interesting places. When I can help it, I try to get paid to go to the places I go. What I don’t do is pine for the “opportunity” to go somewhere — because if I want it, I will make it happen.

These rules and tricks have helped make that possible. Maybe they’ll work for you too.

This post originally ran on Comments can be seen there. A different, expanded version, also ran on