Braindump on approach to writing a technical book.

July 8, 2018. Filed under writing 33

I've been blogging for more than a decade now, and I've always had a loose goal of blending my writing into a book at some point, although timing around that goal has been pretty abstract. A few weeks ago I ran the conceptual exercise of what a book using only my existing writing might look like, and my take away was that it would be a very fragmented read.

While there isn't a unified package for all my content, I think parts could be reworked into cohesive wholes of their own, focused on perhaps engineering leadership or infrastructure engineering.

From there I've spent some more time thinking about the overall endeavor, asking around a bit on Twitter, and I've written up some notes on how I should approach this.


I think there are probably five broad motivations for writing a book:

  1. Wouldn't it be really cool to have written a book?
  2. Let's try to make some money!
  3. This would be a great way to build my career!
  4. Let's try to meaningfully raise the ceiling for practitioners in the field!
  5. Let's try to meaningfully raise the floor for practitioners in the field!

As best I can tell, the first two are somewhat misguided, but the later three seem to be pretty valid. The last two are not necessarily mutually exclusive, but I think the approach, topics and content would be different enough that pursuing both simultaneously would make the degree of difficulty unnecessarily high.

Loosely, I think you should never pick 1 or 2, always pick 3, and then pick either 4 or 5.


Assuming one picked three and either four or five, some more concrete metrics to set goals around might be:

  1. Number of copies sold, benchmarked against comparable books, and previous books by same author.
  2. Amazon popularity rating within category.
  3. Amazon ratings, benchmarked against category.
  4. Format efficiency rating: how was performance compared to alternative publishing mechanisms. How does reach of publishing a book compare to writing the equivalent ~50 blog posts, speaking on podcasts, and so on.
  5. Number of twitter mentions, benchmarked against comparable books.
  6. Enabled opportunities, e.g. for O'Reilly's they give access to their conferences to promote their authors, which creates visibility for their authors

Questions to answer

Thinking about the overall process of writing a book, some questions that would be interesting to answer if one were creating a new publisher:

  1. Are books an effective mechanism to develop a new following?
  2. If an individual is developing a portfolio of content, when are book an effective avenue? E.g. should you bootstrap a following with a book, or should you capitalize on an existing following using books? (Maybe they appeal to different cohorts, so it's a pure return on investment question?)
  3. Is the goal of a successful book to be a self-fueled marketing campaign, or is it possible to actually make money by writing or publishing books?
  4. What is the role of conference and conference speaking in successful book marketing?


Not knowing anything about how to do this, but often being in the position of doing things I know nothing about, my loose sense of the best way to approach this process is:

  1. Write down your motivations for writing this particular book. Are you looking to raise the floor or raise the ceiling? If neither, what are you hoping to accomplish, and what are you hoping to add to the conversation?
  2. Identify existing book which are similar to the book that you want to write. What does each of those books do well?
  3. Using your idea of the book you want to write and the similar books, identify the audience you want to focus on. Is that market large enough to accomplish your goals?
  4. Write the table of contents for the book. If possible, pull together related content you've already written that captures some of those topics, which will help ground the content a bit.
  5. Identify at least ten folks within your target audience, and ask them for feedback on your proposed table of contents. Would they read it? What's most interesting? What is missing?
  6. Iterate on the table of content until folks feel genuinely excited about it.
  7. Take the table of content and then move into heavy outlining, identifying the topics you would want to write in each section.
  8. Pick one section that you think is interesting and write it.
  9. Get feedback from the same group of folks as before on this one section, and iterate on it until folks are excited about it's format, content and quality.
  10. Write everything else, using that one section as the template.
  11. You've written a book.

If folks have approached this differently, please let me know!