Jay Acunzo and I open up the hood and look inside the book writing process.  We covered: research, outlining, drafting, editing, publishing (traditional or self?), the benefit of a podcast, superlatives (best story, most useful research, hardest part, easiest part, interactions with our editors), and practical takeaways for your whether you want to write a book or not.  More info about Jay:  His thinking has been cited in courses at Harvard Business School and by writers at the New York Times, the Washington Post, Fast Company, Fortune, and Entrepreneur.  He is a globally touring keynote speaker, and author of the book Break the Wheel.  Jay began as a sports journalist before moving into tech, holding media and marketing roles at Google and HubSpot, and an executive role at the venture capital firm NextView.


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  • Why this topic? We’ve both written books. And my book is out this week!
  • Context on our books: Welcome To Management.  I wrote the book I wish I had when I first got promoted.  Jay’s book is called Break The Wheel.
    • “Write a book because you think it has to exist.  Not to be a best-seller.
  • The Process:
    • Research, outlining, fan interaction, drafting, publishing — Why an outline is a vital piece of the process.  “The outline is the bones.”
      • “Doing research in public created a system to vet ideas and best practices.” –> Using client interactions as real time research to help test ideas
    • Podcasts – It was extremely helpful for me to be recording while I was writing the book: I was consistently doing research while writing the book.  Interviews, asking questions about writing/books, ideas, etc. I was working full time while I wrote this book and I think that made it better. It forced me to be disciplined with blocking time to write daily.
    • Traditional vs. Self-Publish vs. Hybrid — Jay chose a hybrid approach to publishing his book.  I chose to publish traditionally with McGraw-Hill.  I did a lot of research on the different paths for publishing and chose the traditional route because: I wanted to create options and leverage for myself.  And after I spoke with Casey Ebro from McGraw-Hill I was completely sold on accepting their offer.
  • Superlatives:
    • Platitude about writing/writing books/creativity that you found MOST true during this process? LEAST true?  Most true = Writers write (listen to the James & Kristy Clear story from dinner).  Least true = I’ve read from a few well known authors that you have to dedicate your life to nothing but writing the book.  I found that continuously working and building a business at the same time as writing was helpful. When I do q & a’s on stage after a keynote or on my podcast, I get ideas and prompts to write about…
    • Most useful habit/routine: I learn through talking.  I had regular sessions where I would sit in a room with my Dad and/or my friend Lance (who was a prosecutor for 10 years).  They would give me prompts, ask questions, and we would talk out the book. I would type notes during our sessions, then I would go by myself and write.  In my very first session with my Dad, he said, “Remember, it’s a lot harder when you care.”  He meant this in the form of leading people… And he’s right. But the same is true for writing a book. It’s hard when you care so deeply about the topic of helping people lead others more effectively… Because I understand the ripple effect.  The wake left behind you as a leader.
    • Most surprising lesson: You don’t fully know what you think or how little you know until you put pen to paper.  Writing REALLY forces you to be clear on what you believe. I outline sections and then would ramble on for pages.  The editing process was helpful. I hired an editor/writing coach to help.
    • Best story from the book:   I sent an early copy to Ryan Holiday to read and offer feedback.  He called me said, “Dude, why is your best story in the middle of the book?  You should open the book with that story.” And so I did…
    • What was your editor’s favorite part? Casey Ebro (from McGraw-Hill) said to me, “I read non-fiction business books for a living.  I’ve read hundreds of them.  And your section titled “You Have To Do All Three” in chapter six is the most unique and helpful view that I’ve read about leading, managing, and coaching.”  — That was a great moment.
  • Additional Benefits:
    • Publishing your work online is becoming the greatest networking tool in the world — When done well, you attract the people you want to be around. (David Perell, James Clear have written a lot about this)
    • Writing is the ultimate exercise to help you find clarity.  Sometimes you don’t realize how much you don’t know about something until you try to write about it.  — This can help everyone (especially useful for leaders).
    • Apply to be part of the next Learning Leader Circle


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