How I Wrote Three Books in Three Years

image of a row of books with human-like bookend

Writing a book can be a long, hard slog.

The “miserable” parts of the experience have been documented over and over again. Or just ask any author on a book deadline — or let the thousand-yard stare speak for itself.

Not all of us can have an entire corporation behind them churning out novels, taking the stress off, after all.

And though authors are unquestionably helpful to each other, they don’t always give the best advice. Think how many times you’ve heard this old trope: Just put your butt in the chair and write. It’s true, but that doesn’t help you right now, does it?

I don’t want to give you advice like that.

I want to show that there is a way to publish prodigiously while baking the marketing into your work.

That sounds like a scheme, I understand. But I know this is true because I have done it.

You can do it too

It’s hard to say exactly when a book truly begins.

I sat down to write my first book on June 17th, 2011. I know this because it was the day after my 24th birthday, and I’d left my job, my city, and my home to start it. This was the day I first allowed myself to actually write.

Roughly three years later, that book is done. And so are two others, now all released (along with an expanded paperback of the first). I’m also the editor at large for a prominent media outlet, and in that time I’ve written for publications as varied as CNN, Fast Company, The Columbia Journalism Review, Copyblogger, The New York Observer, Thought Catalog, Forbes, and Marketwatch.

My writing career is still very young. I’m still figuring out where it’s going. But if I have one thing to share it’s this: it can be done.

There are strategies you can develop to ensure that you will always be publishing content, and that your content can find an audience. And I’m happy to show how those were developed.

Here are the seven strategies I’ve developed that have allowed me to write three books in three years along with countless articles and columns:

1. Always be researching

I’ve talked about research before on Copyblogger, so I won’t tread on old ground. But I will say that my notecard system and commonplace book have been essential to my productivity as a writer.

The beauty of this system is you collect what you’re naturally drawn to, so you start to recognize patterns and interests, which gives you direction for what you should write next. It’s a great cure for writer’s block.

  • What are you clipping, saving, and writing down?
  • What is a common theme or subject matter?

That is the muse is telling you where you should go next.

For instance, I was first introduced to Stoicism at age 19. Since then I’ve been following the thread in my reading and observations in life. So when it came time to write my latest, I had not only read something like 100+ books related to the topic in some way, I had already amassed and organized all the material. All I had to do was put it on paper. It wasn’t as if I was suddenly scrambling to start from scratch.

I had also written about the subject many times over the years on my blog and saw the kind of response it got and knew it would resonate with readers.

In fact, all my books have come from these note cards and from blog posts.

Because I am always researching, I have somewhere close to 10,000 cards on various themes. Each potential book, once it gets enough cards, gets its own box. And I just bought a box for my next book … before the paint is even dry on this new one.

This is the kind of feedback loop that creates impressive returns in your writing.

If you are constantly ingesting new material through research, you will naturally follow threads that keep you interested and most importantly — writing.

2. Know where you’re going (have a plan)

An author friend recently told me that he’d written 115,000 words for the book he was working on; a book that contractually was only going to be 60,000 words. And worse, it was only just now that he’d really figured out the thrust of the book.

It almost broke my heart.

Obviously there are many different ways to skin a cat, and I’m not hating on another writer’s style because there are many legitimate ones. But this writer could have written that book in half the time if he’d simply started with a clear outline before he started.

I strongly suggest that writers avoid the temptation to “find the book as they’re writing.” It’s not going to happen. And if it does, it will be a costly discovery.

Crack the code of the book first. Understand the whole before you address the particular.

Writing is easy — there are thousands of graduates out there every year who can do it. But being able to wrap your head around a big idea and knowing how to present to the reader? That’s the tough part. That’s where the race — and the sale — is won.

It’s not only about where you’re going with your book, but knowing where you’re going as a writer.

For instance, on my first book, I moved across the country to write the manuscript before I’d even sold it to a publisher. I knew this was the next big step for my life. Yet, even then the gem of the idea for my Stoicism book was there.

For The Obstacle Is The Way, I sold it in August of 2012 (also for a six-figure advance) just weeks after Trust Me, I’m Lying came out, because I was already planning my next move.

Because my research for that book was nearly done (ultimately the book’s 40,000 words took a little over three months to write), I was able to squeeze in an ebook in between the two releases.

The point is not to go flailing into the process churning out page after page — or book after book — with no defined structure or purpose. All you do is cause more work down the road when it comes time to make a finished product.

You must put in the time, crack the code of getting the material for your book, structure it, and have a spreadable message before you get to writing.

You must map out the path if you ever plan to make it to your destination alive.

3. Use everything you do as fuel for something larger

In The Obstacle is the Way, I write about great icons in history who used the adversity and trials in their lives as fuel, instead of getting buried by it. I take the same approach in my writing.

This isn’t something I came up with. It was passed to me by my mentor Robert Greene, who has a saying:

It’s all material.

He means that everything that happens in your life can be used for something useful, whether it’s your writing, your relationships, or your new startup.

Frustrated about someone wronging you? Follow the example of Demosthenes, who became the greatest orator in ancient Greece essentially to get vengeance in court against the guardians who stole his inheritance. In other words, even terrible things can drive you and produce some benefit.

Trust Me, I’m Lying came out of my frustrating experiences with a broken media system. I couldn’t stop talking about it, but I never felt like people really understood how bad it was, so I had to write about it.

My second book, Growth Hacker Marketing, came from an article I wrote about a development that was affecting the marketing industry. I was confused by it and was trying to figure it out for myself. That process led to an unexpected (and unsolicited) book deal.

Writing is ultimately about communicating part of the human experience to the readers. Sometimes it’s a business experience, sometimes it’s an emotional struggle, sometimes it’s an escape.

The point is: your life has to fuel your work.

If it doesn’t, you’ll have a harder time connecting with an audience. You’ll have a harder time getting up to work every morning.

Use what happens to you, good or bad. Write about what you know and feel and experience. Write what only you can write, not what you think other people want.

4. Have something to say

My theory on writing books is that you have to have something you really must say. Anything less than that and you’re doing it for the wrong reasons.

As George Orwell once said:

Writing a book is a horrible, exhausting struggle, like a long bout with some painful illness. One would never undertake such a thing if one were not driven on by some demon whom one can neither resist nor understand.

James Altucher has a great technique: he writes what he is afraid to reveal about himself. He puts it all out there.

When you’re sharing what’s important to you, when you’re sharing truth that you feel people need to say, you will find that the difficult parts of writing fall away. You’ll stay up late at night to work on it because it matters to you. You’ll put up with rejection because you have no choice.

I knew I had to write my first book, so much so that I quit everything, my job, the city I had lived in for past five years, and moved across to country to get it out. In some ways, that’s what it takes to propel you across the chasm.

We live in an attention economy. The most important thing is saying something that no one else is saying, or even better, can say.

Having something to say is actually an effective marketing tool. Who hasn’t read a book (or rather quit reading a book) where it’s transparent that the author either isn’t really into what he’s writing or he’s just trying to sell an idea, instead of writing with authority in a compelling way. That is bad marketing.

It’s also just a bad way to spend your relatively limited amount of time on this planet.

5. Make commitments

This is one of my productivity secrets in my writing.

If any good opportunity to write comes my way, I almost always say yes, even if I don’t think I’d possibly have the time to. What I’ve come to find is I always find the time, and it’s in stretching my limits that I become a better writer.

When other people are depending on me for my work, I’m not going to let them down.

But when it’s an internal, personal commitment, that’s when the excuses and the Resistance start to creep in. Which is is why I’m committed to doing at least two articles a week on Thought Catalog and Betabeat, plus my monthly reading list newsletter, plus copywriting I do for clients.

That means my estimated output per year, without counting my books, is at least 100,000 words … and probably much more. This has led to literally hundreds of articles across many sites. I’ve even written something like 200 Amazon reviews.

It’s like your rent — you never miss it because you have to pay it.

This is why I’ve resisted self-publishing so far.

I could easily self-publish my next project. But the plain reality is that books are hard to write, and as you trudge along you’ll make a million excuses. I couldn’t tell you how many times I’ve seen this just with potential clients of mine.

But when you read the date your book is due, and sign your name on that publishing contract, you know you’re going to hustle and work to write that book.

It’s why I’ve turned in a book proposal for my next book before my latest one even comes out: to keep the chain going, to have a commitment that I know I have to meet so Resistance doesn’t have the time or space to creep in.

6. Work with great people (don’t try to do it all yourself)

Too many writers take the approach of locking themselves in a room writing until they think that they have a finished book. Or they pay someone on Craigslist to edit for them or design the cover. And then they blog about how cheap it was.

I can imagine why!

This is the exact wrong strategy to take.

You are the CEO of your book. As the CEO, it’s your job to make sure that you surround yourself with great professionals who will make this company a success.

It’ll be the best investment you make while you’re writing your book. Behind every seemingly “overnight” book success was a team of people who all contributed in a major way.

I’ll open the kimono a little on who I use and what I pay:

  • For all three of my books I’ve hired Nils Parker at Command+Z Content to edit them (which cost about $10,000 each).
  • All three of my book covers, which I love, were created by Erin Tyler — which cost about $3,000 each.
  • And even though I have my own marketing company that has worked tirelessly on my books, I’ve also hired a traditional business book publicist to support us in pitching legacy media — to the tune of $30,000+ dollars.

But it was well worth it to work with pros who made the project not only better, but more successful.

You don’t have to use the people I do. There are tons of professionals out there doing great work. You just have to find them and have the strength to relinquish control to them.

The point is: I hire great people to take tasks off my plate or do things that I’m not qualified to do.

It’s also about paying it forward. I got my start as a researcher for a successful author. Now I want to give other people a chance.

7. Link it all together

For me there is no separation of work and life.

Both fuel each other, both make each worth doing.

It’s what allows me to produce so much without burning out, because each part sustains the other.

Too many writers separate their “work” life from their real life so they can justify simply spending time “writing” without any urgency. They don’t make the connection that it’s all part of a larger whole that can be used to their advantage.

And they all link back to each other in some way.

In my personal life, I can’t tell you how many times I’ve thought of a great line or solved an intractable writing problem while running or swimming.

I take insights I’ve learned from a client crisis and use them in my writing like I knew it all along.

I learn lessons on marketing my own projects, which I can use as case studies to bring in more clients.

I try to make connections in everything I do to create a feedback loop that is always producing something.

As you strengthen this muscle, the more connections you can make … and the odds you’ll come up with something new or creative increase.

Remember … it’s all material

No one will argue that writing is an easy profession.

Getting someone to pay you for your words isn’t easy.

But there are strategies you can use to simplify the process and transform what you can produce.

By simply asking, “How can I use this to my advantage?” more often, we can find ways around the inevitable obstacles that come along when writing.

By finding ways to use the adversity we face as fuel for our writing, we can never be stuck or lost without direction.

Now over to you

Which of these seven strategies resonates the most with you?

What in your life can you use to your advantage right now that you haven’t been?

Join the discussion over at Google-Plus.

Flickr Creative Commons image “The Reader” courtesy of Kevin Dooley

About the Author: Ryan Holiday is the bestselling author of The Obstacle Is The Way. Based on timeless philosophical principles and the stories from history's greats, The Obstacle Is The Way reveals a formula for turning difficulty and tribulation into advantage. Ryan is also the author of Trust Me, I’m Lying and Growth Hacker Marketing and currently an editor at large for the New York Observer.

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