Finished the Manuscript — Reflections on the Writing Process

Nearly two years ago I was sitting in a hotel room in Reno, Nevada with my basketball team at a tournament. I was focused on two things: dominating the boards on the court and dominating the buffet line in the restaurants. But I also had another side activity: my book. While my dear friends played poker, Austin reminded me I was parked on my bed banging away on the keyboard.

Yesterday, I turned in my manuscript (MS) for my book My Start-Up Life: What a (Very) Young CEO Learned on His Journey Through Silicon Valley. Since I am sitting here with just one of my nearly 200 excellent Christmas songs on iTunes humming from the speakers, I thought I’d reflect on the writing process.

First, some stats.

# Words in Final MS: 60,000

# Words Written But Not in Final MS: 30-40,000

# Pages in Microsoft Word: 260

# of Full Iterations / Drafts: At least 25

# of Hard copy pages printed for editing: ~8,000

First Line of the Book: It didn’t start with a dream.

Now, the process. My writing process was unconventional as far as non-fiction goes. I started writing a long time ago in quasi journal-entry form. I wrote an entire manuscript and then did a proposal and ultimately signed with a publisher (late September). Then I significantly re-worked the manuscript, with the help of my editor, to fit the new vision agreed to by the publisher and me. The new vision called for a more traditional "business book" rather than strict memoir. The book is my story written in a way that can aid and inspire other entrepreneurs.

Here are a grab bag of thoughts:

Romanticization of Writing — For some reason I had this idea that writers stay up late at night with tea steaming on the side and write, write, write, and write…unable to stop. Maybe this is true for fiction, as you can get lost in the story. For my book there were times when I spent a couple hours doing solid writing, but the vast majority of time is writing a little and then editing, editing, editing. Changing words, re-organizing paragraphs, adding a better last line, etc. This is not nearly as romantic! It’s hard work.

Writing about Yourself — I believe it’s an order of magnitude more difficult to write about yourself than something / someone else. My book is not all about me, but I’m the central character and I write in the first-person voice. It is difficult to develop an authentic "voice," for one, and two, there’s the constant battle to project a tone that’s not arrogant but not too soft, either. Fortunately this blog gave me good practice.

Writing about Others — As a true story with real, living characters, I had to strike a balance between honesty and consideration for someone’s professional and personal reputation. In some cases I simply could not be as honest I would like. There are several pseudonyms used in the book.

Big Picture vs. Granular Edits — The easiest kind of editing to do is suggest word changes, fix grammar, and remove sentences. The hardest kind of editing to do is big picture ideas — does this paragraph fit in the big picture? Does this chapter work? What about this big issue that’s unaddressed? I found that most of the people who reviewed the MS focused on the granular stuff, which is super helpful in its own way. But now I know why the first time you read anything you’re supposed to read without a pen in hand because it can get distracting to start editing on the sentence level.

Feedback from Others — I received feedback from about 15 outside people. The core group included my editor, a secondary editor, my Dad who reviewed many drafts, Jesse Berrett who reviewed very early drafts, and then a half dozen business people who looked at a draft in early November. The outsiders who gave feedback had different profiles — ie young and old and different kinds of jobs. Since I was constantly making edits and updates, I knew they’d be reading an out-of-date manuscript. The quality of the feedback I got from reviewers varied. I mailed my business friends the MS on October 14. I turned in MS December 1. In that period of time I think it got 50% better.

I’m a huge proponent on getting feedback from others on your work. I recommend all writers distribute their work far and wide as often as they can. Be prepared to get contradictory suggestions. Also be firm about obtaining "candid feedback" — when you ask for opinions of friends, they might sugarcoat.

Obsession — During the last week of writing / editing I became totally obsessed with the MS. I had no idea it’d be this intense. I started canceling meetings and during the few dinners / lunches I kept scheduled I felt jittery and anxious to get back to my Word document. During the last two days I spent basically all light-hours working. I didn’t sleep very well through it all. The good news is I felt like by the end of this all-consuming period the MS improved quite a bit, the bad news is I felt like it could be even better! (Although, really, you could edit something for 10 years. At some point you must stop. 🙂

Plagiarism — Given my age, this was of heightened concern for me (and the Publisher). I’m happy to say I used no ghostwriter and did not, to my knowledge, plagiarize anywhere in the text. But I know there will be suspicions. I tried to be extra judicious in the Sources section to give proper credit for others’ ideas….at least those ideas I can clearly attribute to someone else. I’m sure I’ve internalized other people’s ideas and writing style without even knowing it.

Coordinating Actions — To reiterate the unromantic nature of the craft, I spent a huge chunk of time not writing but "coordinating actions". I had to get "braintrust" entries from friends who are contributing to the book, organize and collate edits, sign papers and fill out forms, and generally work with the Publisher on a variety of non-writing tasks such as legal agreements, copyright stuff, images, and so forth. If you’re not interested in organizing / communicating / facilitating, and solely want to be a "writer," you need to find someone to help you navigate the details.

Remembering the Reader — The best non-fiction remembers the reader on every page. A non-fiction book is a product a customer will pay money for. You’re always trying to serve the reader.

Tools — I used Tadalists to manage editorial tasks, marketing ideas, and a host of other random to-dos relating to the book. I wrote in Word in one big document which I backed up almost daily. I also had an "editing floor" document, "chapters in progress" document, "writing ideas" document, and a variety of other containers on my computer. I used del.icio.us to track things on the web that I wanted to use in my book.

Actually Doing It — 81% of the U.S. population feels like they have a book in them. This has been me for many years. Now I can say I’m a published author. I’m excited that I actually did it! I will probably write more books in the future.

So, what’s next? The book comes out in May. There’s a lot of marketing legwork to be done before then. In one sense, the work has only just begun…

Thanks to everyone who helped make this manuscript a reality. In particular: Neal Maille t, Peter Economy, and David Casnocha, among the dozens of others.