After I released my first book, Clueless at The Work: Advice from a Corporate Tyrant, all sorts of people came out of the woodwork asking me the same questions:
- Why did you write a book?
- How long did it take you to write the book?
- How did you get published?
- Can you help me finish my book?
- Should I self-publish?
- Who did the artwork?
So, I thought I’d answer some of these questions for anyone who’s curious.
Why did I write a book?
My friend Andy and I have had so many conversations over the years about management. In early May 2019, we put a Google Doc together threatening to write a book together. It started in secret so our wives wouldn’t get angry with us for taking on “yet another project.” I initially put a bunch of chapter titles in the doc. Andy added some of his own chapter ideas. More importantly, he added a lot of comments and questions for me. Questions like:
Andy: “Is there a focus you have in mind?” Me: “No.”
Andy: “What’s the problem this book is solving for people?” Me: “I don’t know.”
Andy: “What will this book provide for people?” Me: “I don’t know.”
As you can see, I had a real vision for the book.
There’s more to it than that, of course. Between 2015 and 2017, I was writing and teaching professional development and self-awareness cohorts through Kensho Education, a startup I co-founded with some friends (Allen, Anila, and Cory). Cohort participants, friends, and industry peers kept asking me for a book containing the course material. In 2018, I was asked so many times that I thought the universe was telling me I needed to write a book.
When Andy and I talked about writing a book together, I kinda got excited, but it didn’t go anywhere until…
How long did it take me to write the book?
I woke up at 5:30AM on the morning of May 26, 2019 with a vision of the book’s framework. It was one of those epiphany moments every creative type hopes for. I ran to my laptop and typed 5,000 words in about 3 hours.
The next day, I woke up early and wrote another 5,000 words. And the next day, and the next day. Then I went on a retreat with my mastermind group and kept writing. 5,000 words a day. Then I met my family in Seattle for vacation and kept writing. 5,000 words a day. I asked my publisher about minimum book length and he said, “A respectable book needs to be at least 70,000 words.” After 14 days consecutively writing about 5,000 words a day, I had 70,000 words. (Somewhere, there exist photos of me and an iPad on vacation writing like a maniac.)
Getting to 35,000 words was a real challenge. Hitting that number was a major milestone for me. It meant that I was actually going to write 70,000 words. I sincerely doubted I could pull together enough material for that number, but it became a reality after a week. Day after day, the words kept coming. Once I had 70,000 words in my Google Doc, I slowed down, did some editing, rested a few days, then got back to writing as much as I saw fit. I wrote another 25,000 words in the next 1–2 weeks, then spent 3–4 weeks editing it. My publisher did a lot of editing as well.
All in all, it took about me 8 weeks of work (3–4 hours a day) to write the book. This was after a few years of research, writing, teaching, practicing, mentoring, coaching, correcting, etc. The material had already percolated in my brain. I had already assembled over 200 pages of notes that led to the book. So, it’s not like I pulled 95,000 words out of thin air.
As a Catholic, I honestly believe the May 26 epiphany was a gift from God. When people ask me how I did it, I use all the words in the last few paragraphs, but the reality is that I felt incredibly motivated by a vision. I didn’t need to think about it, or work particularly hard. The book fell out of my fingers and into a document.
How did I get published?
Most authors go through hell trying to get a publisher. I wish I could relate. My hobby YouTube channel, Make Weird Music, led me to an eccentric named Ken Coffman. Ken is a multi-faceted electrical engineer who runs an independent publishing company and a guitar shop in his spare time. Over the years, he kept suggesting I write a book. He wasn’t prescriptive on the topic, but recommended I either write about the dozens of weird music interviews I’d conducted, or about the professional development material I’d written for Kensho Education.
There were some emotional challenges for me and Ken is a hard-nosed businessman. I made several suggestions on visual ideas and Ken’s response was, “I’m sure there’s another publisher out there who would be happy to publish this book if you want to do that.” In the end, publishing with Ken made my life a lot easier and there’s a lot I didn’t have to think about after I handed over a manuscript. I’m super grateful for him and am honored to call him a friend. We have done many ambitious, ridiculous projects together over the years.
Can I help you finish your book?
Probably not. My wife is a professional writer. She writes hundreds of articles per year for various publications. I am just a person who plopped a lot of words into a document this one time. To even begin to compare what I did to what my wife does every day is an insult to the craft of writing. It’s a travesty to equate her work with my project. So, I don’t think of myself as a writer. She’s the writer. However, I can offer some perspective on how I wrote my book.
First, I started with an outline of material. I wrote the book in a Google Doc and used their standard “Heading 1,” “Heading 2,” “Heading 3,” paragraph styles and filled in a lot of the outline as I went. The more I wrote, the more ideas I had for the book, which I could easily insert into the outline. Having the outline made it clear for me to navigate where to insert and move content.
The bigger the outline grew, the less concerned I was about filling the book with tons of words. It’s a lot easier to write a 280-page book if there are 90 chapters. The outline showed me that I could write two or three pages per chapter and have a decently-sized book.
Second, I ignored my emotions about the book. Truth be told, I’d tried writing the book before, but got too wrapped up in how I felt about it instead of just writing the book. It’s likely I only finished the book because I felt like there was some divine intervention involved. I was able to detach from the judgments I made about the book’s content. Besides, I’d already had enough experience with failing to capture an audience in other areas of my life that I told myself, “Worst case scenario is no one reads it.” By imagining that no one would read the book and by literally not caring if it sold a single copy, I wasn’t really bound to any attachment or expectation.
Third, I firmly believe in the “first pancake problem.” Anyone who has ever made pancakes has burnt the first pancake in the batch. The rest of them turn out fine and the best pancakes are the last ones cooked. That’s how I feel about this book. In my mind, the book is decent and good enough for publication. With the first one out of the way, now I know my next books (yes, there will be several) will be much better. So, by accepting that this book would be my first pancake, I was able to write it and not worry.
Should you self publish?
I have no idea. There’s a lot of crap I don’t have to deal with by having a publisher, but the tradeoff is the money made per copy. Furthermore, having a publisher allowed me to focus entirely on the content of the book and not the metrics surrounding the book. If you are thinking of self-publishing, I highly recommend you reach out to my friend Rad, whose self-published book, Your Default Settings, became a best-seller on Amazon and is extremely enjoyable. He knows how the system works and was able to game it. I don’t.
What about the artwork?
I must thank the incredible Dave Woodruff for coming up with the concept and the execution of the book artwork. He is a professional and has designed several books. I was fortunate enough to work for the agency he founded, meltmedia, for five years. Working with Dave has been some of the most fun creative work of my life.
That’s my son on the cover, by the way. I’m on the back in the same uniform with the wings because I think adults are basically just big children pretending to be important.
Was that helpful?
I never promised to be helpful, but I’m happy to talk about the process. (Message me if you’d like me to speak at an event or guest on your podcast/video.) I love creative projects and I look at this book as “just another” creative project. Like a painting, or a song, or a video. A lot of people put significant weight on the idea of a book. Yes, it’s a lot of work, but it’s not more work than writing and recording an album (I’ve done several of those), or putting out hour-long artist interviews with transcriptions and hand-animated quote callouts (I’ve also done several of those), or building an audio/video production studio in your backyard, or recording a 9-hour audiobook in the studio you built with your bare hands.
You can order Clueless at The Work: Advice from a Corporate Tyrant from Amazon (paperback, e-book, or audiobook) and Barnes & Noble.
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