I’ve been in love with books ever since I read the Great Gatsby in high school. After reading This Side of Paradise, which is loosely based on F. Scott Fitzgerald’s undergraduate experience at Princeton, I wanted to be a writer. But it was 1995, the internet was in its infancy, and there wasn’t any way to share your work. So I sat in my bedroom, wrote short stories, and read books.
Ever since high school, I’ve gravitated towards bookstores in every city I visit.
- When I auditioned for the Northwestern School of Music, I spent most of the day at the Barnes and Noble in Evanston
- Right after I moved into the dorms at Berkeley, I went to a bookstore on Telegraph Avenue.
- Anytime I find myself in NYC, I try to find a great bookstore.
Good things happen in bookstores. The aisles of a bookstore, the floor to ceiling bookshelves, and pages between the covers have been my escape into worlds where everything is unknown, and the possibilities are limitless. My love for books eventually translated into a passion for writing.
I started school at Berkeley thinking I was going to be an English major. When a recruiter at Accenture told me they didn’t hire English majors, I abandoned my dream of being a writer. After I finished school, I started writing again.
- When I graduated from college, I wrote a 63-page memoir in 8 days.
- When I got fired from my first job, I wrote a 25 page expose about the startup from hell.
- When I was the social media intern at Intuit, I started a blog. I didn’t get a job offer from Intuit, but MBA students who found my blog in the years that followed contacted me to ask about the experience and some even got hired.
When you create a world on the blank page, you’re unshackled from the limitations of reality and free to express anything you can imagine. You selectively shape memories, carve details, and build narrative monuments of self-expression.
I have been writing in some capacity or another since my early 20’s. By the time I graduated from business school in April 2009, the internet had evolved. With a minimal upfront investment, anyone could publish their ideas on the web. Since starting that first blog in 2009, I’ve self-published 2 books, interviewed more than 700 people for the Unmistakable Creative Podcast, and written two traditionally published books. This is what I’ve learned about writing books.
The Book Deal
In 2012 I had a phone call with a woman who helped writers get book deals. She said I wasn’t ready. At the time I was upset. But that turned out to be a gift from the universe. The next two years gave me the time to develop the habits and systems necessary to write a book.
A few months later, when I was interviewing Julien Smith, he turned me on to the habit of writing 1000 words a day. Since he had one of the most popular blogs on the internet, it seemed like a no-brainer to give it a try. In the months following our conversation, I ended up writing three new articles a week, a newsletter for our podcast subscribers, and self-published two books, one of which became a Wall Street Journal Best Seller. In 6 months this simple habit changed my life so much that it’s still something I do almost every single day. After the book came out, I wrote an article about how writing 1000 words a day changed my life. The piece went viral on Medium.
Despite the success of my self-published book, there were no publishers interested in talking to me. Fast forward to 2 years later, after 5 years of writing on my personal blog, 100’s of articles on Medium, and producing a podcast for 5 years, an editor at Penguin found the article I had written 2 years ago and sent me an email saying she wanted to talk about writing a book. If there’s one thing I learned from that experience, it’s that creative work is a process of planting seeds for the person you want to become eventually.
After a few months of conversations, my publisher made an offer for me to write two books. The first was to revise and expand my self-published book, and the second was to write a book based on the 1000-word a day article, which became An Audience of One: Reclaiming Creativity for Its Own Sake.
Once you get over the temporary high of your dream coming true, the real work begins. Now you have to write a book. Unlike a blog post, it’s not something you can start today and finish tomorrow. You have to be able to structure something linearly and write upwards of 50,000 words on one idea. This is why many bloggers struggle to make the transition from blogger to author.
Every writer has a different process for finishing books. Ryan Holiday’s approach is incredibly detailed. When I interviewed Amber Rae, she said: “that’s not going to work for me.” Both are great writers and have finished books. I’ve borrowed ideas from many people to come up with the process below.
Some people get impatient, and as a result, they sign contracts for low advances with shitty publishers. The result is usually shitty books. As I said to my friend Azul Terronez on the Born to Write Podcast “you might have a publisher who is backing you, but at the end of the day, it’s your name on the cover. You’re the one who is going to live with this piece of work for the rest of your life. Make sure it’s something you’re proud to put your signature on.”
Choosing Your Subject
In a recent conversation on the Unmistakable Creative, Dani Shapiro said: “the work chooses you.” In my own experience, I believe that to be true. If you looked at the New York Times Bestseller list and attempted to reverse engineer the creation of one of those books in your efforts, it’s almost guaranteed that you’ll fail. You overlook the one variable that throws off the equation for success, and that’s YOU.
Throughout the history of business, people have spotted trends and rushed into business to capitalize on them. Some succeeded. More were rushed right back out of business when tastes changed. The first and most essential step in the creation of a perennial business or project for us, then, is to avoid making this mistake. — Ryan Holiday, Perennial Seller
I believe that what you’re destined to write about reveals itself through an ongoing attempt to write. An Audience of One is a book about creative habits and developing a creative practice. The bulk of my articles on medium fall into that category. What We Should have learned in school but never did is an idea I had been thinking about for more than a decade before I ended up writing an article about it.
With every book an author is attempting to answer a question:
- For Unmistakable: Why Only is Better than Best, my question was “what makes people stand out with their creative work?”
- For An Audience of One, my question was “how can people find more joy in their creative work?”
- For the book idea, I’m currently exploring, my question is “how can we overcome our social programming and thrive in adulthood when our programming has failed us?”
A few weeks ago when I was stressed about the launch of my new book, someone texted me and said: “we teach what we need to learn?” Each one of my books has been about teaching myself what I needed to learn.
The ultimate nightmare for an author is to be 25,000 words into a manuscript, turn it into an editor, and have to start over from scratch. It delays your publication date, causes you to rush, and can even lead to writing a worse book.
One of the conditions of my book deal was that I had to work with a writing coach. Ryan hires an outside editor for all of his books. Now I wouldn’t ever write a book without one. Usually, the editor at your publisher is working on 20 titles at the same time. They don’t have the bandwidth to work with you throughout the process. Because you don’t get their feedback until you turn in sections, an outside editor keeps you from having to start over from scratch several months into the process.
Before I do any writing, my writing coach Robin and I spend a month putting together an incredibly detailed outline. Much like the book itself, the outline reveals itself to you as you work on it. First, I make a list of all the topics I want to write about in a book. For An Audience of One, that list included:
- Deep Work
As you can see, it’s an incredibly vague start. After figuring out what to write about, you have to then come up with a structure. This is one of the most challenging parts in my opinion. For my last book, we used surfing as a metaphor for life and business. For this book, Robin suggested the idea of using “listening.” Since listening is my primary activity as an interviewer, it was a perfect choice.
Once we’ve decided on a structure, we start to put each of the topics into the structure and expand on each topic. Then we submit a draft to my editor, wait for her feedback and revise it accordingly. I don’t start writing the book until my editor and agent have signed off on it.
From there you’re left to get to work and expected to deliver a manuscript by some date six months from now. Nobody is holding you accountable. Nobody holds a gun to your head. You have to be self-motivated.
When you’re writing a book, everything and everybody in your life are at risk of becoming material. The fact that you’re writing a book becomes the lens through which you see the world. Everything is in some form or another research. But instead of mindlessly browsing the web, all of your media consumption is a deliberate choice.
Books: If you pick any book off my shelf, you’ll see underlined sections in every single one. I jokingly told Chase Jarvis “I’m dreading the day when someone I’m dating picks up the 48 Laws of Power or The Art of Seduction off my shelf.” I’ve tried many different methods for remembering and taking action on what I read:
- I’ve experimented with Ryan Holiday’s Notecard System
- I write about what I read in many of my articles
- I’ve used Tiago Forte’s method of using Evernote to build a second brain
The one that was most effective for me was using Evernote. A few days after finishing a book, I’ll grab it off of my shelf, and create a file in Evernote where I put an image of the book, and an Amazon Link. Then I’ll type out all of the quotes that I want to be able to access. Many of the author quotes in my Medium articles are the result of this process. I also use quotes for every writing session. Since your brain makes progress towards a goal based on the perceived distance to that goal, starting every writing session with a quote reduces the perceived distance.
When I get to a section in my manuscript that’s about a particular subject, I’ll look back at my Evernote files for any books about that subject. If a quote can support or reinforce a point I’m trying to make, I’ll work it into that section. The research from the books you read is more of an art than a science. Some of what you’ve captured will be completely useless. But as Ryan said to me of his notecard system, just one could be enough to build a career off of.
Choosing what to read is also an art. What you consume will be reflected in what you create. Since I was writing a book about the creative process, I started with books like The Artist’s Way, The Creative Habit, Deep Work, and The War of Art. But I didn’t limit myself to books about the subject matter of my book. I read personal development books, memoirs, and more. If I got one nugget, even a quote that I could use, it often planted the seed for a section or chapter.
Podcasts: Since I’m the host of the Unmistakable Creative, my own interviews ended up being a treasure trove of insight. In addition to interviewing people, I read all of their books. When it came to podcasts, I didn’t necessarily document what I’d learned. For some strange reason, my referential memory is like an encyclopedia of insight from the people I talked to. I remember most of what I’ve heard, and it shows up in my writing. When I listened to the WBEZ podcast about the making of Oprah, I ended up writing about it. But I don’t recommend this for most people. If you hear an idea, document it in some way.
Conversations: Dates, walks on beaches with friends, conversations with family members, dinner parties, and happy hours all give you fodder for writing a book if you pay attention. For example, I asked all of my family members about their various creative endeavors and discovered that I come from a long lineage of amazing cooks, prolific photographers, visual artists, fashion designers, and musicians.
Movies: I also watched several documentaries. Sometimes the most unexpected ones gave me the story I needed. For example, when I got to the sections on deliberate practice, I watched a documentary about high school basketball players and learned about a kid named Parker Cartwright. His training regiment became one of my examples.
There as many intricacies to the process as there are writers struggling to find their way. It’s a matter of discovering what works for you and eliminating the shoulds. — Dani Shapiro, Still Writing
If there’s one thing that prevents authors from writing a great book, it’s getting caught up in the hype. “Grandiose fantasies are symptoms of resistance,” said Steven Pressfield in the War of Art. The ancillary bullshit like your social media presence or header graphic doesn’t matter when you’re in the midst of writing a book. Fantasies about fame and fortune do more harm than good. As I said in An Audience of One, Forget about the bestseller lists, the shining lights. Above all things what matters is the work itself.
You can employ as many tactics as possible, or you can make better art. If you make better art, your tactics will be far more effective.
After five years of writing every day, I know what I need to do my best work. Early morning stretches of uninterrupted creation are essential to my creative process. I do my best work between 6 am, and 9 am. I have a ritual. I set my coffee to brew, meditate for 10 minutes, pour myself a cup and get to work.
I always read before I write. Sometimes I return to books I’ve already read. Other days I read something new. This makes it much easier to come up with ideas to write about. After I read 50 pages, I crack open a Moleskine and start writing. Every writing day begins with incoherent psychobabble, shitty first sentences, and shitty first drafts. Once I’ve filled three pages in a notebook, I open up my laptop and my distraction-free writing software. Writers have to warm up like athletes and my first 30 minutes are my warm up. My goal is to hit my word count. Out of 1000 words, I might end up with one or two good paragraphs which I add to my manuscript.
Sometimes you end up writing about things that have nothing to do with whatever you’re working on. Don’t resist this. The muse for some reason prefers the scenic route. You veer off the beaten path, you stop to check out the view, but eventually, you find your way back. You discover magic and meaning in the unexpected detours and diverse landscape of the writing process. Your outline ends up being more of a compass than a map.
After I hit my word count, I add whatever I’ve written to my manuscript. Then I review changes and queries from my writing coach. If it’s something I can address immediately, I do. If not, I write down all of her questions in my writing software and make it part of my assignment for the next morning.
Midway through a book, I submit a draft to my editor and wait for feedback. This ends up being useful because it gives you time away from the work, which helps you get unstuck and come up with new ideas. By the time a book finally goes to print, there have been hundreds of edits and revisions.
The process is different for every writer. Some people count words. Some people track the hours. Others write on specific days of the week. But the one thing that anybody who finishes writing a book has in common is a process. It’s about finding one that works for you.
Don’t judge a book by its cover is a nice cliche. But it’s mostly bullshit. Considering it’s one of the thousands on a shelf at a bookstore and one of the millions on Amazon, the cover matters A LOT. Visuals are a huge part of our brand at Unmistakable Creative, and I want all my book covers to reflect that.
Mars Dorian designed the covers for my two self-published books. In working with him for five years, we’ve developed a process. He usually gives me loose sketches of a few different options. Then we narrow it down to 2 or 3, and he creates variations based on those options until we have a final product. This is the same process that I’ve used for book covers. It usually takes about 15–20 versions before we land on something that I’m happy with, a few of which you can see below. While I’m sure I drove the designers at my publisher crazy, nearly every one of our readers have raved about the cover.
Marketing And Promotion
A product that doesn’t have word of mouth will eventually cease to exist as far as the general public is concerned. Anything that requires advertising to survive will- on a long enough timeline- cease to be economically feasible. — Ryan Holiday, Perennial Seller
You could be the most talented writer in the world. But if you have you no audience for your work, it’s going to be a hard sell for any publisher. Publishers don’t create a market for your books. They come to you because you already have one. Your platform is the foundation on which all of your marketing and promotion efforts are built. Marketing and promoting your book takes just as much work as writing it.
Usually, there are about nine months between when you submit the final manuscript and the publication date. Your marketing should start as far in advance of the publication date as possible. When I asked the team at Digital Natives what causes subpar book launches, they said that authors come to them too late in the process.
When it comes to promotion and marketing, no magic bullet leads to book sales. In my first meeting with Digital Natives, the agency I hired to help with the launch, the first thing they said was that marketing begins with a great product. You could employ every tactic imaginable, but if the product sucks, all the marketing efforts in the world aren’t going to make it a best-seller.
We had five main marketing channels for our book launch.
When it comes to selling books, your email list is your single most significant asset. For the last two years, it’s been the primary focus of our growth efforts. It’s the one asset that you have complete control over. To nurture and grow the list, our marketing team created six free ebooks, and I wrote a series of emails sharing content and ideas from the book with our current subscribers
I’ve been writing on Medium since 2013, and it has been our most significant driver of email subscriber growth. It’s also where most people read my work. Every week I wrote an article related to the subject matter of the book (all of which are linked below).
- How Writing 1000 Words a Day Can Change Your Life
- Don’t follow your passion, Pay Attention to What you Find Engaging Instead
- 7 Essential Traits for Anyone Who Wants to Build a Career in the Arts
During the launch, Medium also featured an excerpt from the book. Like any platform, what you get out of it is based on what you put into it.
With podcasts, we had a two-pronged approach. The first was our own podcast. For the eight weeks before the launch, in our Friday best of episodes, we featured a former podcast guest who was in the book. During the month leading up to the book launch, we recorded new episodes with people who were in the book and had them focus on a specific subject area.
The second part of our podcast strategy was other people’s shows. The greatest asset you have when it comes to podcast appearances is relationships with the hosts. Having interviewed more than 700 people, I had existing relationships with a lot of people. Some of them had been guests on Unmistakable Creative. Others were longtime listeners and fans. You might want to promote your book, but the most important thing is to articulate the value that you can provide for someone’s audience.
Since this book was about creative habits, I asked a friend for an introduction to someone at Creative Live to talk about doing a course based on the book.
Chase Jarvis interviewed me on the Monday before the launch, and I taught a course on designing systems for creativity on the day of the launch. Given the subject matter of the book, it was as targeted an audience as we could ask for.
A lot of people want to land media appearances on the biggest possible platforms. But that doesn’t necessarily lead to book sales. You’re much better off reaching a smaller but highly relevant audience with your book.
Ryan Holiday echoed this sentiment in Perennial Seller: “I’ve seen clients with pieces on the New York Times “Most Emailed” list — as viral as you can hope to be on that site-and watched as the Amazon rank for the book hardly budged.”
A massive social media presence doesn’t guarantee book sales and a non-existent one doesn’t prevent them.
- Cal Newport doesn’t have a social media presence, and he’s built a successful blog and sold thousands of books.
- I have another friend who has a massive and highly engaged Facebook following, but it didn’t lead to many book sales.
The same can be said for many authors. I’ve written extensively about the downsides of social media. The one thing to remember about social media is that it’s rented land. I heard Tim Ferriss say to a podcast guest “having a business highly dependent on Facebook is like owning a profitable McDonald’s on top of an active volcano.”
While we did share a ton of content leading up to the launch, the most valuable part of our social media effort was when people in my network shared the book. When fans, friends, and family members shared the book, people who didn’t know my work at all ordered the book. For the most part, nobody buys books written by authors they’ve never heard of. In my own experience, nearly every book I’ve purchased in the last few years was because of a recommendation.
The Work Continues
Even though you spend upwards of 18 months writing a book, the work doesn’t stop after it’s published. It’s just beginning. If you’re serious about having a long-term career as an author, you need a long-term view. There are many things about creative work that are difficult and out of your control. The one thing that’s not is your effort. After a week of promotional efforts that included a live taping of Unmistakable Creative and appearances on multiple podcasts, I came home and did what made all of this possible in the first place. I sat down to write.
It might be the second, third, or fourth book that puts you on the map in the eyes of the world. But in the eyes of any creator who has achieved recognition or critical acclaim, it’s the cumulative effort:
- The thousands of hours spent in a quiet room mastering her craft
- The years on end of rejection, failure and people questioning your sanity
- The persistence, hope, and endurability combined with the faith that you’re capable of making something great
It’s never one moment, but a lifetime of work that makes you capable of one day creating a Perennial seller.
Gain an Unfair Creative Advantage
I’ve created a swipe file of my best creative strategies. Follow it and you’ll kill your endless distractions, do more of what matters to you, in higher quality and less time. Get the swipe file here.