How I Wrote My Manuscript in 3 Months

Make your words cost you

Recently, I submitted my 70,000-word manuscript (two weeks early) to my publisher, Tarcher Perigee, an imprint of Penguin Random House. The manuscript is for my second book, which is based on my first book, The Quarter-Life Breakthrough, a guide for millennials to find meaningful work, which I self-published. My book tells the stories of 20- (and 30-) somethings who are reinventing their careers based on meaning and discovering how to work with purpose (and pay their rent). The self-published edition took me about 12 months to write (including outlining, writing and editing a total of eight 45,000-word drafts, publishing and marketing). It became a best-seller on Amazon, a #1 top-rated job-hunting book with over 80 5-star reviews, and generated a good deal of press.

Over the past three months, I took my 45,000-word self-published version, removed what wasn’t working, refined my message, researched and wrote a bunch of brand new stories, added practical exercises I had been testing throughout the year, and created an even better 70,000-word product that will hit bookstores sometime in the second half of 2016. It’s kind of like when a new band releases their own 8-track EP, and as the band keeps touring, the EP gets some buzz, and a record label is like, “Yo, we dig the EP, how about we take the 6 best tracks, get rid of the worst 2, and add a few new tracks, including a solid single.”

I still have a long way to go with editing my second book, but this post offers a few lessons I’ve learned about how to build the habits and routines that have helped me write two books in three years. If you’re looking for information on how to self-publish, or how to get a book deal with a major publisher, this particular post won’t be helpful, but check out this piece I wrote on whether you should self-publish your first book, and this post on how I marketed my first book.

Deadlines matter.

Writing a book takes time — a lot of time. But too much time is a threat to your creative potential. A deadline is what separates the “doing of the idea” from just the idea. A deadline is what separates an “artist” from a “aspiring artist,” an “author” from a “person working on a book.” In my experience, projects with deadlines get done, projects without deadlines linger like that little leak in the bathroom sink faucet you’ve been meaning to fix for months (but still haven’t fixed).

You write when money is on the line.

For this book, I had a publisher’s deadline, which meant, quite simply: I didn’t get paid unless I met my deadline. Not writing simply wasn’t an option. When you have to write in order to pay your rent, you write.

Quick-aside: you don’t have to have a fancy publisher to have a deadline or to have a financial stake in your book. When I self-published my first book last year, it took me about ten months to complete my manuscript. I ran a crowdfunding campaign to raise $13,000 to hire an editor and cover designer for the project. My editor and I set deadlines, and although my second draft ended up taking many months longer than the first draft, I still finished. Because of my Indiegogo campaign, I had $13,000 in my bank account that wasn’t actually my money; it had to cover the costs of producing and shipping books to over 500 supporters from 40 countries. So whenever I thought of procrastinating and not writing (which is to say, every day), a little voice would creep into my head and be like, “Whoa whoa whoa Smiley, what about that dude in Iceland who bought your book? He’s counting on you. You owe him a book. You can’t just take his $20 and run, that’s stealing! Oh my god, I’m a thief, I’m gonna end up in crowdfunding jail unless I finish this fucking book! I guess I better write today.”

Make your words cost you. Run a crowdfunding campaign and commit to a date you’ll send out your completed book. Pay a professional book editor. Tell your friend you’ll pay them $500 unless you finish by your deadline.

Writing requires extended focused attention.

I am a professional multi-tasker. In less than 30 seconds, I can go from typing this blog post on Medium, to taking a sip of green tea, to writing an email to a close friend, to texting a girl I think is super cute to see if she wants to do yoga on Saturday, to buying a ticket for a conference on Eventbrite, to having a bite of a Honeycrisp apple, to liking three photos on my Instagram feed. The problem is, while multi-tasking is an effective way to ask someone out while you work, it’s not an effective way to write a book.

Personally, I can’t write unless I have a full day (or at least 4-5 straight hours) of focused attention only on writing. This means when I fill my days with meetings, phone calls, lunches, extended social media use, or social events; those are days I don’t write. This means that if someone “wants to have lunch,” they have stolen a day of writing from me. I have to leave my house at 11:30am to meet them at a cafe downtown, we eat from 12:30–1:30pm, we talk a little bit more as we finish up lunch, suddenly it’s 2:15, then I stop to buy a chocolate chip cookie at the bakery because I’m standing in front of a delicious bakery selling chocolate chip cookies, then I bike home, and suddenly it’s 2:45pm. Nearly four hours of writing time, gone. If I’m lucky, I write a few paragraphs that day, but I probably just check a few emails since it’s 3pm and I’m tired.

Create your optimal writing space.

I’ve always found it interesting when I tell people I’m a writer, and they say, “Wow, I’m so jealous you get to spend your days at a café.” I’ve never written more than a few sentences at a café, and besides for a place to buy a coffee or tea, I think cafes are the last places writers should hang out. Why? Because you can’t get any writing done at a cafe. The music is too loud, and it’s either The Lumineers Pandora station or the Kanye Pandora station on repeat, and while I love both The Lumineers and Kanye, I get sick of writing to them. The person next to you is talking on their phone. Another person is watching Game of Thrones on their laptop. The two people on the other side of the cafe are having a conversation about how their friend finally finished writing her book— which is great for her — but totally fucks up your flow.

If cafes are bad for writing, then co-working spaces are even worse. You expect me to go to a place with unassigned seating, where half the people are on Facebook, the other half are playing ping-pong, there’s free booze, and where 12 of my friends of my work (including a girl I have a huge crush on that never glances back at me) and expect me to get writing done there? Please.

The writers I know who actually write, don’t have fancy offices. They have a desk (usually in their own apartment as to avoid commute time), where they sit down every morning and write. In my San Francisco apartment (which I share with five roommates), I have two small desks in my bedroom that face a window overlooking Grand View Park in the Inner Sunset. I keep a stack of books like The War of Art, Bird by Bird, and The Artist’s Way, on my desk to inspire me, and I have quality speakers to listen to a rotating playlist of Tycho, Explosions in the Sky, The American Dollar, Thelonious Monk, and yes, sometimes The Lumineers and Kanye. Maybe once I write my third book, I’ll have enough money saved up to get a place where I can have a writing office separate from my bedroom. Until then, I’ll write from home. What does your optimal writing space look like?

Design your optimal writing day.

Annie Dillard once wrote, “How you spend your days is, of course, how you spend your life.” Spending time writing is, of course, how you write. Everyone is different — some people are most creative before the sun rises, some do their best work late at night. Obviously, a writing routine for someone with a full-time or part-time non-writing job is going to be different. There is no “right way” to spend your day writing, it’s about discovering how you do your best work, it’s about creating your personal routine (and sticking to it). For me, my optimal day of writing looks like this:

Smiley’s Optimal Writing Day

8:00am: Wake up. 10-minute meditation, morning stretch, and 30-minute morning run.

9:00am: Breakfast

9:00am-12:00pm: Morning writing time. On a good day, I’m sitting at my desk writing by 9:01am. I start with 2–3 hours of writing entirely new material. The morning time block is when I do my best work, so if I ever have to schedule a call or a meeting, I always do it after 3pm.

12:30pm: Lunch. I try to eat outside and avoid eating at my desk. I like to read an article from The New Yorker or a book during lunch.

1:30pm: Afternoon walk or email break if necessary

2:00pm: Afternoon writing session. I keep going on new material, and when I hit a wall for the day, I go back and read the morning’s material and try to make a few edits. Sometimes I hit a complete wall around 3pm, and then I just call it for the day and go outside.

4:00pm: Afternoon walk, phone calls if necessary

5:00: Emails, phone calls, other non-writing work

6:30: 30-minute afternoon run (unless I run in the morning)

7:00pm: Dinner, time to hang with friends, or time to watch a movie

10:00pm: Reading before bed. I try to read at least one book that’s similar to the book I’m writing to get ideas, as well as one book that’s completely un-related, also to get ideas. No matter what, no computer use after 10pm since if I look at a screen before bed, I have trouble sleeping.

11:00pm: Journal before bed

11:30pm: Sleep

Know your 3 “writing MUSTS”

To be clear: I don’t always stick to this schedule — in fact, I have probably followed this schedule only twice in the last seven days. I’m not a r0bot, but that’s not the point. The point is to know what your day looks like when you’re at your best. For me, even if I don’t write for 5 hours every single day, I know my 3 non-negotiables, my 3 “writing musts”:

1. I MUST write first thing in the morning before I start checking email or having phone calls or meetings.

Let me give you an example of why this is so crucial. This morning, instead of writing first thing, I decided to check my email at 8:53am. I opened an email from a millennial podcaster, asking if I wanted an introduction to another millennial writer that just wrote a book about his own quarter-life crisis. It was very kind of him to offer an introduction, but the net result of checking this email is that I clicked on this author’s website, spent 15-minutes reading the Kindle preview of his book, and then spent another 30-minutes doubting myself, being like, “man, my book topic is so played out. I better find something else to start writing about.” Soon, it was 9:47am, and I wasn’t writing, I was reading a Buzzfeed article that a friend of this author had posted on Twitter. Basically, to summarize, I wasted an hour of writing time because I checked one email. I’m excited to connect with this author in the future (but not during my optimal writing time!).

2. I MUST avoid social media to write.

The majority of my two books were written during extended 2–3 month social media sabbaticals. During this time, I didn’t use Facebook, Twitter, or Instagram. Occassionally, I had to send a Facebook message or check the location for a fun event I wanted to go to, but social media is a writer’s worst nightmare. First of all, it’s a time suck. You start by liking a baby photo, then you read an article making fun of Donald Trump, then you die laughing watching Larry David be Bernie Sanders (“man, this shit is so good, I just have to post it on Facebook”), and 47 minutes later you’re watching clips from Inside Amy Schumer. Anything is more exciting than writing — watching Amy Schumer is like 4,567 times as exciting as writing. Second of all (and even more dangerous), is that social media makes me worry about what other people are writing. The doubt creeps in, and I feel like what I’m writing isn’t even worth my time, which is to say, I don’t write. Social media is an incredible tool for writers to share their work and build a platform to connect with readers, but that comes after you do your writing for the day.

3. I MUST exercise outside to have a productive day writing.

Research suggests that taking frequent breaks at work, leads to greater productivity. One study by The Energy Project, an employee engagement consulting firm, found that employees who take a take break every 90 minutes report a 30% higher level of focus (as well close to 50% higher levels of creativity and well-being). Breaks are especially crucial for writers and artists. Not only do I release stress when I go outside, but I often have my best ideas on my morning run. When I get back from my run, I usually rush to find a sharpie and post-it, so I can write down the brilliant ideas I had for a new story to tell or how to change a paragraph, before they escape my mind. I’ve even thought of building some sort of contraption that allows me to stick a sharpie in my running shorts, so I can write down ideas on my hand as I run (“Smiley, why don’t you just run with your phone?” Because that would defeat the entire purpose of taking a break outside!).

Saying no = saying yes to your truth

The most useful strategy I’ve found for completing two manuscripts is to completely remove myself from social expectations and responsibilities. This means, during August and September, the months where I wrote the bulk of my manuscript, I used an email out of office, which said something to the effect of, “Thank you for your email. I’m currently writing my manuscript, which I have to deliver on deadline on October 15th. I’ll be responding to email after that date, thank you for understanding.” I felt guilty about ignoring peoples’ emails for weeks, but the surprising thing was that no one seemed to mind. I got emails back being like, “Go get em’ Smiley, keep writing! I’m inspired by your dedication!”

When you say no, you say yes to your truth. No one really cares if you respond to their email tomorrow morning. No one really cares if you wait a few months to schedule a meaningless “let’s touch base” phone call or coffee. The only one who can prioritize your writing is you. Don’t blame your friends or social events for taking up your writing time. Instead, start saying no. Start putting your work, your truth, first. Your friends will understand, and you’ll find yourself with more than enough time to write (and get your other work done).

You make time for what matters most.

At Camp Grounded (tech-free summer camp for adults), my fellow counselor Bricky St. James told me something quite powerful. Your heart knows which commitments it actually wants to show up for. If writing a book is something you actually want to make space for, you will make space for it. If it’s not, it’s probably not the right time for you to write a book. When you commit to a time-consuming project like a book, you become aware of what matters most, since you have to say no to so many obligations. Although I had to complete my manuscript in less than three months, I still made time to take a weekend off for the Hive Global Leaders Program and two full weeks off for two Camp Grounded’s in North Carolina and Austin. Camp Grounded and Hive are that important to me, and I’ve realized that the communities in my life that make me better and change my friends’ lives are non-negotiables. When I don’t spend time with my communities, I lose the inspiration behind my writing and I don’t have anything to write about. Moving forward, I know I have to be conscious about creating a fruitful harmony between solitary writing time and inspiring community time, which is far from easy.

Break up your book into small, manageable assignments

The greatest challenge facing an author with an unwritten manuscript is feeling like you’ll never finish. My strategy is to start in the middle and give myself daily or weekly tasks that are manageable. For example, I never start with the Introduction or the first chapter. You can spend months trying to write an Introduction, stressing, trying to get every single word exactly right, and then by the time you actually write your book, your Introduction isn’t even relevant anymore.

  • First lesson: write your Introduction last.
  • Second lesson: break it up. In my favorite book about writing, Bird by Bird, Anne Lamott talks about the power of short assignments. Whenever you’re stuck, you can start with a prompt that gets you writing a paragraph or two. After a few paragraphs, you’re golden. This is how I approach my books as well. I start by taking a large stack of post-its and on each post-it, I write one short story that I want to tell. It could be an anecdote, an example, a quote, a person’s name, a case study, a character, a place, a lesson, a relationship, a vacation, or a moment in my life. I don’t worry if the stories are in chronological order or even if the stories will end up making the final draft, I simply jot down all of the stories I think I want to write about.
  • Then, I take the post-its and spread them over a huge wall. Once all the post-its are spread out, I begin to constellate them by theme or topic. Some post-its don’t really fit into a particular theme, and that’s fine, I leave those to the side. But usually, the post-its are placed in 7–10 “categories,” which become the foundation for the 7–10 chapters of my book. For me, storyboarding is the coolest part of writing a book. I now have two full 1-gallon Ziploc bags of post-its from my two books and when I start writing my third book, I’ll go back to my post-it bags to see if they’re any amazing ideas I missed.
  • Instead of writing the book from page 1, I start with one post-it that is calling to me that day. I don’t worry about where the story is going to fit in, I simply write the story that is calling to me that day. Often, the stories I write end up being something completely different than my intention upon starting — but this material still ends up making it into the book. I save each “post-it story” as a separate Microsoft Word doc. That way, instead of being intimidated by only being on word 150 of a 70,000-word manuscript, the task is far more manageable: I’m typing word 150 of a 1000–1500 word essay, which makes it feel like I’m only writing a blog post, not a book.
  • When I have a few post-its written in a particular category, I paste the docs all together and try to create a coherent chapter. This process takes a long time, because it involves making smooth transitions and discovering what material just isn’t working in terms of each chapter’s overall message. I still keep a separate Word doc for each chapter — again, it’s a lot more manageable than scrolling through a 150-page document.
  • Once your book is in categories, you can set mini-deadlines for each chapter. For example, “By next Friday, I’ll finish the first draft of Chapter 4.”
  • Only when I have all my post-it stories written and organized into coherent chapters, do I start thinking about writing the Introduction.

Friends don’t make good editors

The biggest mistake I made when writing my first book was to give the first draft of my book to friends for early feedback. I was like, “Sweet! Ten of my friends are going to give me edits of my book — for free! I’ll save a few thousand bucks.” What happened? Nine friends said the draft was awesome. One said it sucked. I figured I was golden. Then, my actual editor read the book — and told me I basically needed to re-write the whole thing. I decided to listen to her, and I’m glad I did.

Your friends love you and want your book to succeed, but that doesn’t mean they know how to edit a book. In my experience, it’s hard for friends to give truly brutally honest feedback. So you end up with half your friends telling you to take the book in one direction, and the other half telling you to do the opposite — in other words, you end up wasting your time. Instead, pay (read: PAY) one (read: ONE) professional (read: PROFESSIONAL) editor (read: EDITOR) to edit your book. Work with your editor to create a unified vision and scope for your project. In the last year, I think at least 323 people told me, “Smiley: I want to help you — I’d love to read and edit a draft of your new book, free of charge!” This is incredibly kind of my community. But I always replied, “Aw, you’re the best, thanks so much for the kind offer! But I already have one editor in charge of my project. You’re more than welcome to bake me cookies.” And you know what? I finished my manuscript in three months.

Confidence = words on the page

Remember those kids in high school, who always complained about how bad they were going to do on a test, even though you, and everyone else knew they were going to ace the test, because they ace’d every single test since first grade? Don’t be like those kids. Pretending to be humble only hurts your creative potential. Instead, own your shit. Be confident in your work. If you expect to fail, you will fail. If you tell your friends that you’re a struggling writer that can’t hit her deadline, you will be a struggling writer that can never hit her deadline. If you tell your friends that you are writing an amazing book, and that you’re on schedule, guess what? You’ll write an amazing book and hit your deadline.

Where one book ends, another begins

Momentum is everything when it comes to writing. I turned my manuscript in three weeks ago, and I’ve already found myself slipping out of my daily writing practice. This is because I no longer have a deadline and a concrete project to work. Money is no longer on the line. So, following my own advice, I’m giving myself a deadline to come up with my new project. I’m going to commit to a new book idea before Christmas. In the two months between now and Christmas, my plan is to keep a running list of all my book ideas in my journal. I already have 14 ideas listed. I’m committing to writing about each idea each week. Not only will this keep me writing between now and when my book comes out next year, but it gives me a chance to test which subjects I actually enjoy writing about. The ideas might spin into something completely new and unexpected, and that’s exactly the point. In my curiosity, I’m hoping to find my third book.


Smiley Poswolsky is the author of The Quarter-Life Breakthrough, a guide for millennials to find meaningful work. His follow-up book will be published by Tarcher Perigee/Penguin Random House in 2016. Follow @whatsupsmiley and get free quarter-life resources at smileyposwolsky.com.