“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 book. It 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 Catalog.com. 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 ThoughtCatalog.com. Comments can be seen there. A different, expanded version, also ran on Fourhourworkweek.com.

Painters like painting, the saying goes, writers like having written.

Are there exceptions to both sides of this rule? Of course. But anyone who has run the gauntlet and written a full-length book can tell you, it’s a grueling process.

You wake up for weeks, months or years on end, and at the end of each working day you are essentially no closer to finishing than you were when you started. It’s particularly discouraging work because progress feels so elusive. Not to mention that the pages you find yourself looking at rarely match what was in your head.

It’s for this reason that “wanting” to write a book is not enough. It’s not therapy. It’s not an “experience.” It’s hard fucking work.

People who get it into their heads that they “may” have a book idea in them are not the ones who finish books. No, you write the book you HAVE to write or you will likely not write it at all. “Have” can take many forms, not just an idea you feel driven to get out. You know, Steig Larsson wrote the Dragon Tattoo series to pay for his and his wife’s retirement.

If you honestly think you might be fine if you nixed the project and went on with your life as though the idea never occurred to you–then For The Love Of God, save yourself the anguish and do that. If, on the other hand, this idea keeps you up at night, it dominates your conversations and reading habits, if it feels like you’ll explode if you don’t get it all down, if your back is to the wall–then congratulations, it sounds like you’ve got a book in you.

Some tips:

-Writing a book is not sitting down in a flash of inspiration and letting genius flow out of you. Most of the hard work is done before you write–it’s the research and the outline and the idea that you’ve spent months refining and articulating in your head. You don’t get to skip this step.

-One of the best pieces of writing advice I ever got was to–before I started the process–articulate the idea in one sentence, one paragraph and one page. This crystallizes the idea for you and guides you on your way.

-Taleb wrote in Antifragile that every sentence in the book was a “derivation, an application or an interpretation of the short maxim” he opened with. THAT is why you want to get your thesis down and perfect. It makes the whole book easier.

-Read The War of Art and Turning Pro.

–James Altucher wrote a very good post on “Publishing 3.0” over the weekend. Read that.

-Don’t think marketing is someone else’s job. It’s yours.

-Envision who you are writing this for. Like really picture them. Don’t go off in a cave and do this solely for yourself.

-Do you know how a laptop feels when you think you’ve closed it but come back and find out that it’s actually never shut down? That’s how your brain feels writing a book. You’re never properly shut down and you overheat.

-Expect your friends to let you down. They all say they are going to give notes but few actually will (and a lot of those notes will suck).

-Work with professionals. If you’re self-publishing, that means hiring them out of your own pocket.

-When you hit “writer’s block” start talking the ideas through to someone you trust. As Seth Godin observed, “no one ever gets talker’s block.”

-Plan all the way to the end, as Robert Greene put it. I am talking about what the table of contents and the bibliography are going to look like and what font you’re going to go with. Figure out what the final end product must look like–those are your decisions to make. Or someone else will and they’ll make the wrong choice.

-Good news: You used to have to worry that no one would ever see this thing you put your whole soul into. (It’s such a scary thought that John Kennedy Toole killed himself over it.) Well, you don’t have to worry about publishers rejecting you anymore. Obviously, it’d be better to have a major house backing you, but remember, you can always self-publish. So fuck ‘em if they reject you.

-Have a physical activity you can do. That will be the therapy. Trust me, you’ll want the ability to put the book down and go exert yourself. Plus the activity will keep you in the moment and many of your best ideas will pop into your head there. (Personally, running and swimming work for me.)

-Have a model in mind, even if you’re doing something totally new (read The Anxiety of Influence: A Theory of Poetry if you’re interested in this psychologically). Thucydides had Herodotus, Gibbon had Thucydides. Shelby Foote had Gibbon. Everyone has a master to learn from.

-Plan for it to take longer than expected. Way longer.

-As Fitzgerald wrote in The Crack Up, avoid the temptation of “going to somewhere to write.” You can write anywhere–the idea that you need to travel or go away to put words down is often just a lie or a procrastination. (That being said, for my first two books, I moved thousands of miles away to places I didn’t know anyway. This can work.)

-You’ll “lose your temper as a refuge from despair.”

-Don’t talk about the book (as much as you can help it). Nothing is more seductive (and destructive) than going around telling people that you’re “writing a book.” Because most non-writers (that is, the people in your life) will give you credit for having finished already right then and there. And you’ll lose a powerful motivation to finish. Why keep going if you’ve already given yourself the sense of accomplishment and achievement? That’s the question the Resistance will ask you at your weakest moment and you might lose it all because of it.

-“Don’t ever write anything you don’t like yourself and if you do like it, don’t take anyone’s advice about changing it. They just don’t know.” – Raymond Chandler

—

Everyone has their own tricks and rules and they’re going to be a little different than mine. I’m not saying every single one of the tips above will work.

But the idea around which they are based is not a controversial one. Books are hard. As in one of the hardest things you will likely ever do. If you’re only marginally attached to your idea or the notion of writing a book, you will not survive the process. “Wanting” is not enough. Write the book you HAVE to write, and if you’re not at that point yet, wait, because the imperative will come eventually.

The good news is that everyone who has been there understands. They remember and empathize with Thomas Mann’s line, “A writer is someone to whom writing does not come easily.” You can ask them for advice. They will be, in my experience, incredibly understanding and approachable.

Good luck. And don’t let this kick your ass.

This post originally ran on ThoughtCatalog.com. Comments can be seen there.