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How I Wrote Three Books in Three Years

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?

Best-selling author Ryan Holliday doesn't want to give you advice like that.

He wants to show you that there is a way to publish prodigiously while baking the marketing into your work.

That sounds like a scheme, I understand. But Ryan knows it is true because he's done it.

He'll explain in tomorrow's post. Stay tuned. 

Update: Post now live:

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Paolo Bulletti's profile photoSonia Simone's profile photoMeredith Blevins's profile photoKelly Boyer Sagert's profile photo
What I've found is that, as a writing career builds momentum, it becomes both easier and harder. It becomes easier because research starts to overlap as you become an expert in a certain area(s). It becomes harder because expectations increase (both yours and that of readers) and because you find more and more pathways you might want to take.

Thanks for such a detailed piece about your experiences. Appreciated!
I started a commonplace book without knowing what it was called. I named it Mind Vomit. On the first page I even have contact information and offer a reward for its safe return. I use several notebooks for each project I am on, so it really helped to have that one notebook that wasn't attached to a certain project to just brain dump in. Very freeing.

Great article, I will be reading it a few more times to let everything sink in. Thanks.
Now you hear the sound of a sigh. I followed the link to your book on Amazon, GROWTH HACKER MARKETING.  It is fifty-six pages long.  This is not a book, it is a booklet, a pamphlet.  It is barely long enough, were it to be fiction, to be a novelette.  Giving people this sort of blanket information is discouraging. 

Writing with an outline?  Go to any writer's conference and attend a panel.  90% of the writers will tell you they start with an idea and the characters and story take over.  If you want to arm wrestle with the likes of Lawrence Block or Stephen King, go to it.  But the fun and juice is having an idea and taking the ride.

An outline is great for non-fiction.  It is dead weight for fiction.  I believe we need a new category for writers.  If you are writing non-fiction, how-to books, you used to be called a technical writer.  Being called an author is onerous.  I was told by Sue Grafton, several decades ago, that she would whack my behind if I ever did something so pompous.

But, I'm starting to feel that there is a distinction, and we need to make it.  PS:  Writers published with major houses do not have an entire corporation grinding away for them.  These writers still must market, unless the writer is a best-seller.
+Meredith Blevins You have to realize this is what Copyblogger views as good marketing and a good product. Didn't you know they lost touch quite a while ago?
Given that Copyblogger is a business and marketing site, if we give advice on fiction (which we do maybe once a year) we'll say "fiction." The idea that writers of nonfiction aren't authors is a bit ... narrow. 

Also, as a published writer of fiction, I can tell you that mileage varies on the role of an outline, fwiw. I can also tell you that Ryan's advice in this post will serve many fiction writers quite well. Yes, he wrote a short book. He has also written longer books. 

+Greg Strandberg Why on earth, one wonders, are you following the page then? Surely that's a gross waste of your time. 
+Kelly Boyer Sagert "as a writing career builds momentum, it becomes both easier and harder." That's a really good observation. 
+Greg Strandberg, then let's call it writing marketing, not WRITING, don't you think? And, dear writer of the article, let's not introduce someone, a friend of yours, who wrote a book of 116,000 words into the same article as someone writing marketing leaflets. 
Copyblogger, for your part, it would be helpful if you made it clear that there are different sorts of writing.  With a headline of HOW TO WRITE THREE BOOKS IN THREE YEARs?  That is misleading.  Although, those of us on contract, do write three books in three years, plus magazine articles, etc.
+Meredith Blevins You're putting Ryan's writing down without reading it because one of his books is short. I find that profoundly un-smart and un-cool. 

The Obstacle is the Way is 224 pages. Trust Me, I'm Lying is 270 pages. Holiday's work is original and compelling. If you're not a fan, that's perfectly fine -- his work tends to polarize readers, in fact. But you don't get to call one of his books a marketing leaflet without reading it. 

I know many prolific professional writers of both fiction and nonfiction. Many of them produce a book a year or more. It's not some kind of feat of magic. They do it by being tactical, by developing strong habits, and by putting their ass in their chair and getting the words on the page. I wouldn't hesitate to send this post to any one of them, because Holiday is a pro and he has some smart ideas about how to stay productive. 

Do I personally intend to follow every piece of advice in the article? No, because I'm not a newbie looking for some kind of hold-my-hand manual. I can decide for myself what advice will be useful for me. 
+Sonia Simone, then please say 'fiction' as a tag line or in a way that is differentiated from marketing. (I have done both, still do -- no problem -- but let's not behave as if they're the same thing.)
I have been writing and editing fiction for forty years.  I love the arena of self-publishing.  What I have seen though is this:  People have some need, it has to do with status, that pushes some people to call themselves 'an author.'  I have no idea why.  Certainly it doesn't have to do with income.
Sticking the seat of you pants to the seat of your chair with some amount of discipline?  That piece of advice is prime, regardless of whether a person is writing sci-fi tomes or sixty-page marketing booklets. It's not worth blowing off.
I recently read this book. It's great!
Again, we don't typically write about fiction. If we ever do give advice about how to write 3 full-length works of fiction in three years, we will call them novels.  Also, an author is a published writer. I don't think we need a new definition for that word, the old definition works fine. 

Ryan's a very smart marketer but his books are books, not marketing. I'm getting a little impatient with the straw man thing. 

+Jeff Goins I haven't had a chance to read the new one yet, it's good? 
Backing out of discussion.  It is your platform after all, and we stand on different ground.  I know Ryan's work -- he's twenty-six and has done very well in the marketing-media world.  So did Joseph Heller.
Most interesting area of exploration for me in this: #1. I do keep a commonplace book but don't update it as often as I'd like. I like his index cards idea in theory (I am a pen & paper person through & through) but in practice I've never been able to get it to stick, for me a digital tool works better for compiling the bits and pieces. 

But interesting to think about how I can more aggressively/consistently feed my "compost pile." Pondering that. 

Most "that would kill me" area for me is #5 -- I have to manage my commitments or everything goes to hell. I do find deadlines tremendously useful, though.  
I totally agree with the advice about outlining your book first. I think that creative people sometimes have a tendency to want to just get started and let it happen - but this is an awful waste of time when writing. I have wasted a great deal of time this way. Now I have learnt that lesson, I will ALWAYS outline a book first and probably draw up a proposal too before I start writing it. I just wished I had had this advice before....
It's not that hard to write a book of substance every year if you make it a priority and life doesn't intrude.  +Kevin J. Anderson is a case in point, although he averages many mroe than that!
It seems to me that Holiday's method is to do that "let it happen" stage in his research phase, and let the ideas simmer and cook there. I thought his phrase "cracking the code of the book" was a good one.
+Phil Simon agree. If writing books is your job, a book a year is a not uncommon output. 

Of course, a book a year that can pull readers in, engage them, and excite them ... that's trickier. :) But certainly doable with talent, craft, and work. 
+Meredith Blevins non fiction writers should be called technical writers? Are you crazy? How about essayists? Polemicist? Does this mean Franklin D Roosevelt was a technical writer? Thomas Hobbes? A historian? A biographer? Are they technical writers?

A technical writer is someone who creates documentation and instructions. Who's job is to document, with precision, a process or a procedure.

I agree with you that sometimes people apply the label "writer" loosely, but it's an umbrella term for a variety of ways of getting the job done, fiction just being one of them. Ryan Holiday is a writer because he fulfills the dictionary definition.

And an outline isn't a dead weight. You'll save time using one, but a loose one. And never be afraid to steer away from it if that is where the story goes. At least know how you want it to end.   
+Ryan Holiday's question:   Which of these seven strategies resonates the most with you?  

#5 has been huge for me: Commitments. Getting a book proposal done and accepted by a publisher is a huge motivating factor. Then comes deadlines and an editor to help you along the way.  

I LOVE the idea of getting another proposal written and submitted before the latest book is out. One of the biggest challenges I've had as a writer and entrepreneur is getting over that post-project aimlessness. 
+Demian Farnworth , please, name-calling is disrespectful.  You know the difference, very well, between Thomas Hobbes, FDR, and Ryan. (And, I think you may have broken the Guinness World Book of Records for use of question marks.  Phew!)  When you are discussing a topic such as marketing, and you give steps, I think technical writing is appropriate -- nothing wrong with that.  I wrote books for Rodale, non-fiction, and they weren't technical writing. Exactly. Certainly nothing to get excited about, either, but  health books don't interest me.  Writing does.  I have nothing against technical writing or writing marketing copy.  Again, I have done both.  Usually writers have to do all sorts of writing to pay the bills. +Sonia Simone, yes, agree, engaging and exciting readers is a tricky business, and I think it can be done in any form.  Read Stephen King's ON WRITING.  Engaging?  Absolutely.  And, yes, I love spiral-bound index cards.  Fit in pocket or purse.  Great for quick ideas, and great for writing down conversations you've heard at the next table.
+Meredith Blevins A lot of the times engaging books about marketing don't need to be that long, however.  Copyblogger mentions that quite frequently.

I bet if you tallied up the words in one of Ogilvy's books it'd be pretty short, but it's got the pages because of pictures and spacing.  Is that a bad thing?  Doesn't have to be.

I've certainly got a few 'pamphlets' selling on Amazon that probably don't deserve the title book.  None of them come close to the number of reviews this guy Ryan has, even on that shorter book of his.
+Meredith Blevins Actually Meredith, the full paperback for GHM comes out in Sept. But thanks for dismissing it!
+Ryan Holiday good to see you. I'm disappointed, no one is attacking your actual ideas yet. Surely we can fix that! :) 
"Have a spreadable message before you get to writing." This is gold, I hold it close to my heart! Thank you, Ryan, for this advice. I am as new as they come. I have a message for my first book and supporting blog posts to help feed it but am floundering on truly digging in, on where to start, etc. I cannot tell you how grateful I am to have all of your insightful points here. Thank you :) Allison
As a newbie writer, and soon to self publish my own book, I appreciate the article which is very informative for an aspiring writer. It reinforces and supports my journey through the book writing process. The tips are truly invaluable. As a novice, I found the information so appropriate to where I'm currently at as a writer. Yes its all about marketing, and if I were in a position of being able to employ some of the key people who have been promoted on here, I most certainly would. Thank you very much for the article. Wikitoria Smith. Aotearoa, New Zealand.
+Jared Dees To me the big one is Always Having A Plan. My strongest writing comes when I know exactly what I am trying to say. My weakest comes when I let excitement carry me away and I publish before structuring, thinking or editing. 
+Ryan Holiday Yep, having a defined structure or an outline or a detailed table of contents can be a zen like experience. 
I am fairly astonished by the heat in this conversation, and +Ryan Holiday,by people for being so defensive.  (My crystal ball is on the blink, Ryan, so, yes, what I have to look at now is Amazon -- and anyone would dismiss less than sixty pages as being called a book -- although I did not dismiss your work.)  I'm an old broad who has been making ends meet, and then some, for more decades than a lot of you have been alive. If I can engage in discourse with you and weigh words, it seems you'd want to do something similar with a writer who has a lot of miles under her belt.  These miles include winning gold awards in web copy, so it's not just old-school chops.
I love seeing how other writers work, and so many of the methods +Ryan Holiday  uses are applicable in fields other than just book writing. The common book idea is such a great tool. I've always done something like this with scraps of paper, but I like the idea of formalizing it a little bit more so that I can refer back to it more easily (and... you know... not lose them all the time).
I think everyone's really waiting for Ryan's tell-all expose on working behind-the-scenes as marketing chief for American Apparel bad boy Dov Charney...
First, as much as I really dislike it, Amazon/Kindle is changing what we define as a book. There are "books" that are 10 pages, let alone 60. The problem is Amazon does not separate into booklets/reports and they absolutely should in my opinion. It would save so much frustration for both authors who want to write shorter works and readers who want clarity on what they're buying.

That said, I also recently used this analogy on my blog:
If you buy the $1 burger on McDonalds value menu, what did you buy? A hamburger.

If you buy a Red Robin Gourmet burger for about $8-$10 what did you buy? A hamburger.

If you go to fancy bistro that serves an organic burger with heirloom tomatoes, baby lettuce, and artisan cheese on an artisan bun, for $15, what did you buy? A hamburger.

In Amazon's world it's kinda the same thing. Just because McDonalds sells a burger for a buck, does not diminish the value of the bistro creation if you are marketing to the right audience.

Again, I am old enough to remember when libraries had physical card catalogs, so I don't really like the new direction of what a "book" may be defined as. The consumer is the ultimate decision point which has always been the case. As authors (I write nonfiction and yes, I'm an author), we  have to figure out how to work within whatever the system is at the moment no matter if we want to write and sell on the value or gourmet side of things.
Heads up, people: Let's stop talking about +Ryan Holiday's 60-page book. You forget he also wrote two books in the upper 200-page range. More importantly, it has nothing to do with the point of his post. 
I am a big fan of copying out writing that moves you. I think it does very good things for your Writer Brain. 

I actually am nearly finished with hand-copying out Italo Calvino's The Baron in the Trees for the second time. After this one is done I'm moving on to Sei Shonagon's Pillow Book. I do a page or two a day most of the time. Sort of a mental declutter. 
+Sonia Simone Oh I read that one (I've read all of his books). But that's not the "behind-the-scenes" expose I'm looking for...
Wow! And I thought I had an emotional day! :) +Ryan Holiday thank you for your post. And +Sonia Simone thank you for writing a post worth of materials in the comments. :D What is of interest to me? I'm currently rereading +Roz Morris' Nail Your Novel for the umpteenth time. So most of Ryan's suggestions are eerily familiar. No surprise there. I think good writerly habits work whether you write fiction, nonfiction, books, pamphlets, web copy, or blog posts. Certain essentials hold true. When writers ask me the ubiquitous question, "Are you a "panster" or a "plotter"... or a "planner?" I answer, "hybrid." I'm interpreting +Demian Farnworth's "loose outline" to be synonymous. I for one would love to read your fiction, +Sonia Simone I would also love to read a blog post on how your fiction informs your copywriting. Definitely a theme in my own exploration. 
Great article! you put with the correct words what I do since years! many compliments
+Sonia Simone, Yes, regarding your above comment. I think writing fiction, and reading it, is a terrific boost for writing non-fiction.  We learn to hear and use words that give our writing more juice, depth, color, and energy.  All of that is good in ANY kind of writing.  (Except maybe a dissertation...)  Rudolfo Anaya is a sweet friend, and he said to me, "OH~! I hate it when people say to me, 'I only read non-fiction,' as if they are too special to read fiction!"  I think part of that is this culture -- we're supposed to be hyper-brainy, and non-fiction has that tang about it.  Let's write some juicy non-fiction!
What helps me to add more color and power to my nonfiction writing is to go to poetry readings. Poets can craft such incredible imagery in so few words.
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