Book Writing Lessons Learned the Hard Way

In the past two and a half years, I’ve written two books, moved across the country, bought a crack house, and then lived in a construction site for a year while we made it a not-crack house.

I also signed a publishing contract and edited my work more than my aching shoulders would like. Several friends have discussed their own book writing with me and asked about the lessons I have learned. Hence, this piece. Feel free to steal these lessons if helpful. But be warned: you may well learn totally better hard lessons. These lessons took me more than a year to collect. I wish there had been a quicker way. There wasn’t.

Precious Writing Mind

Though I think I’m smart (my mom agrees), and spent many years in fancy schools reading fancy book and writing many (less fancy) papers, writing a book about my ideas in clear, helpful, and nuanced language proved to be way harder than I expected. The problem was never access to a keyboard, or a desk, or…words. The problem is still writing takes “writing mind” and it is a precious and delicate thing. I have to conjure it out of the ether and when it shows up I need to coddle and respect it.

What do I mean by “writing mind”?

I’m in writing mind when I remember I have something to say and I’m comfortable writing words that say it. My mind is calm enough to do the work and I’m excited at the possibility that it may help someone in the future. Wouldn’t it be great if that was every day when I get up? Well, it isn’t and it doesn’t come naturally when I’m doing other fun stuff waiting to “feel like” writing. When I approach my work understanding, honoring, growing, and protecting writing mind, then my work is productive and helpful.

Honoring Writing Mind:

It takes time for writing mind to show up. It takes me about 45 minutes to warm up so that I can actually write good words, and not just lots of words (or very few poor words.) This means that for a long time, I will sit at my computer writing junk; it feels totally non-productive. I've learned that this is just part of the process. As long as I work through the unproductive time, I will (eventually) get to the productive time.

Scheduling (long enough) work time: Because writing mind takes time to develop, I have to schedule sessions long enough to account for this. Most of us begin by assuming we can fit in working on our book anywhere anytime: in an airport waiting for a flight, at a coffee house waiting for meeting, or in moments in a park. For me, this isn’t true. Writing that takes deep thought in long form means that my mind need patience. Rushing the thinking only hurts me.

Managing the Commitment: When I would sit for a writing session, I was overwhelmed by the project of writing a book. It was way too much. So each day I just commit to writing for at least one 90-minute session. Each day, I never commit to finishing a book. I only commit to 90 minutes at a time with my computer. Then, after 90 minutes, I can take a break before I start my next session that is (you guessed it) never more than 90 minutes. What really happens is that sometimes I get into writing mind and want to protect it beyond 90 minutes. Then I may continue for up to two hours or so. Nevertheless, I never commit myself to a longer single session. With enough 90-minutes sessions. I’ve discovered, I will complete a whole book (or more).

Preparation- Getting to writing mind ritual

If I only write when I feel like it, I will never write anything. I will never “feel like writing”. There's always something far more interesting and important to do. This means I simply must schedule a time and at least pretend I will write at my desk. In my schedule, the calendar space is called “crappy writing time” (really.) Writing mind doesn’t show up because I schedule it. So I developed a morning ritual to get me into writing mind. This makes the transition from normal life to writing life more smooth.

Clear Schedule: First I ensure that I actually have nothing else expected of me during writing time. I schedule nothing before noon on writing days. This meant that from eight o'clock until noon I can focus without distractions. Ideally in a four hour window I can work on two 90 min sessions with a break in the middle.

Eat: The first part of my writing ritual is eating. This precludes the excuse of grumpiness or hunger keeping me from writing. It also means that I consider what foods put me in a healthy mind for writing. Some of my favorite foods, like tortillas and soup noodles, make me sleepy. This was not good for days alone with a computer and a dog. On writing days I only eat things that make me feel clean inside and alert. This morning, I had a high nutrition vegan protein shake with berries.

Meditation: Next I meditate and sit in contemplative prayer so that my mind becomes calm and I can focus on my choices, not distractions. The type of meditation changes. I can’t say enough how important this calming is for the transition to writing. Writing time is sacred (set aside) time. Meditation and prayer make it so for me.

Beginning: Then I can walk to my comfortable writing place and set my timer.

A Comfortable Place:

My writing place must be comfortable and pleasant. My body must like to go to this place and settle in.

Standing desk: At one point, I feared my computer and desk. It was uncomfortable to spend hours there at that machine; my body balked. When I invested in a standing set up, I improved my productivity by at least 100 percent. Both my monitor and keyboard are now on movable stands, which means that I can make small adjustments regularly, so my muscles and joints change position over the months.

Soundtrack: Sound makes a difference too. If I play the soundtrack of a busy coffee shop on a stereo behind me, my sense of aloneness decreases. Instead of being in a room by myself at a computer, I have a subconscious sense that there is a bustling room of fun people just behind me (and when I finish this session, perhaps I can join them!). I use the Coffitivity app now. On some days, like today, I play Bach. He helps too.

Writing Time:

Internet Blocker: Focus and calm are the key to an effective writing session. By using an Internet blocker, I release my mental energy. I use Anti-Social Internet Blocker because I can choose exactly which websites to block. I keep access to Google Drive, Dropbox, and a few other useful online resources. I block every website that I know can be a distraction for me. This includes the New York Times, eBay, and Amazon. Whenever I notice that a website has become a distraction, it goes on the block list. With Anti-Social there is no password to unlock a session so I'm not even tempted to unlock for “emergencies.”

Timer: I can only start if I know that my writing session will be short and manageable. I take my mind off the clock by using a timer that alerts me when I’ve met my session commitment. As a practical matter, my Internet blocker serves this function too because the blocking session is timed. Sometimes I use a kitchen timer instead. By keeping timing discipline off my phone, I avoid my phone as a distraction.

Silence phone: Obviously I silence my phone. Duh.

Writing Mechanics :

What we use to get the thoughts out of our head matters.

Scrivener writing program: Scrivener is a program specifically built for writers. You can put all your chapters, references, thoughts, notes, photographs, bibliographic info, quotes, color coding and everything else in one project file.

The most important advantage of Scrivener for me is that it lets me divide the work into as many sections and subsections as I like. I can then drag, drop, combine, and separate any section in seconds. At any particular time, I am only working on a small section and never a whole book; Scrivener keeps my sections organized so I don’t worry about the parts getting lost. Everything is keyword searchable so I can even reference another section in seconds and even keep two sections on screen at once! The project feels manageable and approachable within the program. It sells for less than $100 and is worth far more.

Dictation Software: My thoughts come out more easily when I speak. I now use a transcription software for my first drafts. I think it has increased my productivity by another 100%. I don’t sit at my desk as I dump out first drafts: I pace around the room. My wireless headset allows me to do this. I use Dragon naturally speaking because it is well reviewed.

Dropbox: I keep all my Scrivener files and backups in Dropbox. I know my work is always safe and every draft is saved. Dropbox has saved me more than once.

Unlock the Preciousness:

One of the biggest writing blocks is knowing that the first things that come out are usually terrible. This is just the curse of the first draft and we have to work past it. Our ego will hold us up for months, maybe forever. We can treat these words as precious when they are not. They will get rearranged, laughed at, and red lined before anything is released. This is because we will have smart people go over it first (editors).

Personal Editor: I overcame what I call “preciousness stoppage” by hiring a personal editor. Editor Rose-Anne goes over each first draft and makes it look like someone who writes adult English wrote it. Her job is not to make a finished product or to criticize my rough (and stupid) writing. She smooths the clunky language. This means I never return to my drafts and have to waste energy berating myself. I use the energy to add, refine, and nuance. Good writing doesn’t happen all at once; it is crafted over many drafts.

Berrett-Koehler put my manuscript through four editors in their process. Before that, at least 10 smart people I respect sent notes that radically changed the book. Treating early draft language as precious is a profound waste of energy. The most important thing is that my ideas got out of my head and others can now learn what I have to share.

As a practical matter, Rose-Anne has access to my project file on Dropbox. When I complete a section draft, she will go over it. I then return to that section with no cringing. In later drafts, she would note where I repeated myself, or used confusing explanations or difficult examples. As I got too close to the work, she would help me step back and see it from a stranger's perspective. She made me both better and faster. Each of my first two books found a publisher within a week. I am confident that this was only possible because I had an editor who supported me in making sense and pointed me in helpful directions. Conservatively, I think Rose-Anne saved me a year.

Organization: In the beginning, I used a basic book structure that gave me a place to dump ideas related to the subject. By using the basic structure, I didn't have to worry about developing a strong through line from the start. I could just dump my thoughts into an appropriate section and trust that we could link it all together later. Over time, we refined the order a lot. With Berrett-Koehler, we cut one-third of the book for publication. The structure didn't hold throughout the process, but it did its job, getting me to a full, coherent book. I'll include the starting structure at the end of this post.

Community Accountability

Procrastination is unfortunately part of the writing journey. It will never go away entirely, I can only hope to manage it. There is no super-efficient me who writes fabulously everyday for endless unbroken hours. The process is long, kind of lonely, and sometimes appears fruitless. I’ve addressed this with community.

Integrity Partner: I asked one of the smartest people I know to be my integrity partner. Jason was not one of my close friends. We didn’t see each other very often. He lives hundreds of miles away. But I knew that he is driven, appreciates hard work, and is smarter than I am. I made the ridiculous request that we talk each week so I can tell him what I had done toward building my career and finishing my book. Because he is also kind, he said Yes. Because he is smart, he sees things that I don’t, like trends and opportunities. But that is not his job. As my integrity partner, he knows what I aspire to do and listens to learn if I’m doing it. If I’m not, then he will ask me what will get me going again, no matter little the improvement. Any improvement is better than paralysis. Knowing that I have a weekly call for which I want to have something to share about keeping my integrity for the work helps me focus on moving forward. My books, speaking invitations, and consulting invitations would not have come as they have if Jason hadn’t offered me his listening and support. This is such an important topic that I’ll write more on this separately.

Daily Check-in: Now that I have many projects to work on, naturally I want to work on the easy and less important stuff each day. Writing takes a lot of mental energy. I have a daily 5 pm call with my friend Philip to tell him what I did today. His job is not to judge it. His job is to listen and by his commitment, show me that he is supporting me in a long journey. My call tonight with Philip inspired me to return to this project today.

The broad themes I had do to work on and I hope help you are three fold. 1) Honor your writing mind. Do what it takes to nurture it and coddle it when it shows up. 2) Make your space as fun and comfortable to work in as possible. This is good for your writing mind and your body. 3) Make sure others are supporting you because creating (possible) brilliance on your own is far harder.

All is well here.

Starting Book Structure

• The Need (that you’re writing to)

  • The At Stake: why should they care? / why is this important?

  • Emotional Reality: What readers feel and believe about the problem

  • What readers want to overcome/ the challenges

  • Why this problem happens.

• Author’s story

  • Explains who you help

  • How you help / Why you help

• Big Picture Solution

  • Overview of solution

• Road of steps/ principles/ process for success

  • First

  • Second

  • Third

  • etc.

• Explain what success is beyond the process - what is possible

• Advanced Ideas

  • Dos -Things to make sure you do

  • Don’ts -Warnings and reasons why

• Next step - now what?

  • Call to at actions (at least one concrete step)

• Resources - Tools that will help