What I learned writing a book.

June 8, 2019. Filed under writing 31 elegant-puzzle 9

My favorite story from releasing An Elegant Puzzle is about preorders.

After a few days of preorders, Amazon asks you to ship them a certain number of books that they’ll use to fulfill your orders. They originally asked us to ship some number of thousands – exciting! Then they asked us to double the shipment – more exciting! A day later they asked us to quadruple the shipment, which was almost our entire first print run – concerning.

We took a moment to celebrate.

Maybe this weird book about making ethical management decisions was really going to take off! But I was suspicious. I’d love for the book to be a runaway success, but I’m careful not to get my hopes up, and we started to dig in. As we dug in further, it became clear that the second shipment should be more than enough, and there was simply no basis for sending the third requested shipment.

To this day, we have simply no clue why they requested so many copies, but for me it’s a good summary of the overall process: learned a tremendous amount, had quite a few moments of great pride, and and some spikes of confusion.

As I understand it, a book is not truly written if you haven’t knocked together a blog post about writing it, and who am I to defy that standard. This reflection is roughly structured into the experience, motivations and learnings.


Over the last decade, I’ve written a bit over five hundred posts on this blog, Irrational Exuberance. My writing pace accelerates whenever I find myself in a learning rich environment, which is why I wrote so much in my first two years out of school and over the past three years at Stripe.

As I went into 2018, I wanted to refocus my writing practice and also work on distributing my writing more widely – how could I get more folks reading? I set a goal of one post a month, but momentum gathered and the posts kept popping up, altogether about seventy posts that year.

Around this point, I had a few book publishers reach out with interest, I imagine in large part due to Camille Fournier’s The Manager’s Path establishing a clear market for books focused on engineering leadership. My sense is that Camille’s book is the progenitor of a veritable wave of great books coming out in this area, including Julie Zhuo’s The Manager of a Manager and Lara Hogan’s Resilient Management: it’s a good time to be reading and writing about engineering management.

Of the publishers I spoke with, Stripe Press was the one I ultimately wanted to work with. Part of this is that I’ve gotten to know and work with the team leading that effort during my time at Stripe, but even more important for me is that Stripe Press is a bit unusual: they typically buy completed manuscripts, rather than proposals. This gave me an extraordinary amount of latitude in my approach to writing, the book’s format and marketing the book.

I started by sketching out the content I'd want to write for such a book, then I structured that content into chapters. After that, I wrote each of the chapters as a blog post, which let me get into the "habit of shipping" (to quote my coworker Davin) and to test the content with readers. I wrote one or two sections a week, scrounging roughly eight hours each week from early mornings and weekends. This was a grind at times, but I was able to structure the writing process to glide down the rails of my long-standing blogging habit.

After I'd written the content, I worked with Stripe Press to finalize their interest in publishing, and happily they were.

As an aside, I’m fortunate to have written this book at a point in my life with fewer commitments outside of work, and I am truly amazed by folks who are able to write when raising young children, caring for their parents, or otherwise committed: it takes a great deal of privilege to write a book.

Once we had the content, I worked with Brianna and Tyler at Stripe Press on the book’s details: the cover, translating the diagrams into a unified system, how to handle links, and so on. This was an extremely collaborative process, and being able to lean on their extraordinary taste level elevated the book into something I simply could have never created if I had gone the self-publishing route.

After we merged the content, layouts and art, we printed digital advance copies and started to gather folks to read those advance copies. We were fortunate to get a number of folks to read the early versions and provide feedback, which lead to a number of copy-edits and adjustments. The book’s core content didn’t change much based on the feedback, but everything changed a bit and a few things changed a lot, particularly the chapter transitions.

Once the book itself started to come together, it was time to shift gears to focus on marketing. How were people going to find out this thing existed?

We structured our marketing on the belief that effective book publicity fills three to six months after release. The immediate focus was:

  • working with early readers on blurbs (thank you to Cindy, Oren and Jeffrey – there were also other folks who submitted amazing blurbs that we ended up not being able to fit, and I’m particularly grateful for those as well: let me know how I can return the favor),
  • getting an article to go live on publish day (which came together delightfully, thanks to First Round Review), and
  • adding folks to three different mailing lists for the launch announcement (one this blog’s posts, another that I ran for folks who wanted to know about the release, and a third for Stripe Press). I’d considered setting one up since seeing b0rk’s newsletter, but it was only the upcoming book launch that kicked me over the edge.

Beyond launch week, we’ve worked with a number of amazing podcasts that’ll release over the next couple months, I’ll get to host small events at a bunch of Bay Area companies, I’m speaking at Velocity about investing in technical infrastructure, and I’ll be writing frequently. We’re also looking into a number of different Q&A formats that might scale beyond the Bay Area, maybe a Reddit AMA or some such.

Wrapping it all up, it’s slightly unintuitive but I’m confident that An Elegant Puzzle would have been less cohesive and internally consistent if I had tried to make it myself: I simply lacked the ability to do what we did as a team. Working with Stripe Press I got to make exactly the book I wanted, supported by these deeply talented and thoughtful folks.

It’s been a really amazing experience, and I’m deeply grateful that I’ve gotten to do it. So far, I think the hardest bit will be a small sense of loss after it all quiets down, e.g. the return to normalcy. Perhaps long-term that might even lead to writing another.

There is this sort of classic bind in life that sometimes your biggest opportunities arrive when you’re least equipped to take advantage. Towards the end of finishing the book, I found my patience and joy in writing declined – I was burning out – which isn’t too helpful as my continued writing is a big part of marketing the book, and it’s also a unique opportunity to get more folks reading this humble blog if I can keep writing good things.

I’ve been working on managing my feelings and needs there, while also taking advantage. My writing volume has been high, but I’ve played with formats a bit (book reviews, systems thinking explorations, etc) and have written more short pieces than usual. My energy levels are also very topic specific – there are some posts I really want to write but feel draining to even contemplate, so I’m leaving those for later.

Following that approach, I’ve been able to write a good number of posts I’m proud of so far this year – Good process is evolved, not designed; Metrics for the unmeasurable; Why limiting work-in-progress works; How to invest in technical infrastructure; Privilege’s upward-facing window – without feeling the wall encroaching.


A quick aside on tooling. I wrote the book in Markdown, along with a script that converts each section into LaTeX and merged the sections into an overall book. There is long standing advice to avoid building your own tools for book writing, and I think this is pretty good advice. At minimum, constrain the time you spend on your tooling since the publisher is going to rework all the formatting and such anyway.


My motivations were pretty much the same as why I write in general: I write to learn and share.

In terms of this book in particular, my approach to management is grounded in a different set of perspectives than most others I’ve worked with. I believe this perspective and the ideas behind it are useful, and I hope sharing them will help others to lead healthier teams and more effective organizations.

Another reason I write is building awareness of me and my work. I started out writing when first trying to enter the industry years ago, and still hope it’ll convince more folks that they might want to work together.

There has never been a clear link from writing books to financial rewards, so money has never been a primary reason to write. However, I could imagine that there is long-term professional value from writing a book, much as there has been from writing this blog.

Finally, I am very motivated by having the right mix of new and familiar things in my life, and writing a book was something entirely new. Doing new things – much like getting to help with Increment’s launch, starting to do more public speaking, and so on – has always culminated in good things for me.

Stuff I learned

I went into the process of writing and publishing my book as an experienced amateur blogger, and that practice writing and marketing my writing was hugely helpful for me, but I didn’t understand the book publishing process at all, and I’ve learned a lot by publishing AEP.

Some of the things I learned along the way are:

  • Outline, outline, outline. The only thing I knew going into writing the book was that I should outline everything before I started writing content, and that was good advice. If I wrote another book, I would spend more time outline in detail to build the small pieces more intentionally over the course of the book.
  • Books sell in modest numbers. Even a successful book sells far fewer books than whatever digital widgetry you’re otherwise used to selling. Early on my goal line exceeded the market size – not in the sense of what I expected AEP to do, but rather what I felt was necessary to consider it a “true” success.
  • Print runs are permanent, and errors in printed things last forever. Most errors are minor, but I’m bummed that I misattributed the lead author – the remarkable Ncole Forsgren! – of Accelerate and can’t fix it beyond a tweet and updating the digital versions.
  • Lean on the experts. I went into the process knowing what I cared about, and also knowing the areas I don’t know about. For stuff in the later category, I tried to create space for them to bring themselves into the book. The book, and in particular the cover, does speak to my aesthetic, but the details speak to Tyler’s excellent taste and experience.
  • Marketing is half the work. It’s tempting to think that your work is done once you’ve finished writing the book, but marketing is just as important. The level of time investment that going into personally marketing the book has been quite high.
  • “Twitter sells books.” This insight is attributed to Brianna, and has been surprisingly true: good engagement on Twitter can really sell books. The clearest example being Charity’s tweet which – attribution data here is pretty lacking so this is an estimate – I’d imagine contributed to 500 to 1,000 copies being sold.
  • Reach sells books. The article in First Round Review also drove a tremendous amount of engagement with the sort of folks who benefit from and enjoy books on management and engineering leadership. When the FRR email went out, I had folks reach out that I hadn’t spoken to in years, and books were sold.
  • Critical feedback is golden. A few folks gave critical early feedback, which was some of the most important feedback I got along the way, and I'm particularly grateful for their willingness to deliver it. Honest feedback is very hard to find when writing a book, since you have to find (a) someone who will give hard feedback, and (b) someone who is willing to read your book. That’s a small intersection.
  • Feedback is hard to incorporate. There will be feedback that is both right and very difficult to incorporate. At one point we discussed delaying three to six months to fully rework the content. Ultimately, I felt like it was good enough to go forward with, which I’m glad I did, but I bet the book would have been stronger if we’d spent longer.
  • Getting to know your writing style. I’ve gotten much more feedback on my writing that any other point in my life, including a lot of descriptions that just wanted to describe it as opposed to change it. This has been pretty cool.
  • Blurbs. Getting book blurbs wasn’t precisely harder than I expected, but that’s because I didn’t even realize it was something I would need to do. People who are willing to write blurbs are true treasures. (If you are looking for a blurb for a book in an area I have experience in, I feel like I owe the universe a few favors at this point.)
  • Schedules shift happens. The original release date for An Elegant Puzzle was about a month earlier than the final release date, and I was heartbroken when we missed that date. In that specific moment, I was managing writing burnout and thought I would be able to just squeak over the finish line, then the line moved and I wasn’t about it.
  • Amazon has really fascinating economics. I’ve learned so much about the economics of selling books on Amazon! They take a much larger cut than I initially assumed, but taking such a large cut also allows them to dynamically discount the book to drive sales out of their own cut. I also didn’t figure out I needed to claim my author page until a bit late in the game, about a week before the launch date, which I’m still a bit ashamed about.
  • Selling rights in other languages is weird. I’m still figuring this one out, but after publishing a book you may find yourself getting a number of requests to translate and publish it in other markets. I’m still trying to figure that process out, since I’d like to have AEP available to more people, but I also don’t want to negotiate with dozens of companies separately. (Feels like an opportunity for someone.)
  • QR codes are cool. One of my favorite things we did is that all the endnotes are QR Codes links that you can open with your phone. I think there are a bunch of ways to do this better than we did – use a short-link service to have shorter links that support smaller QR Codes and to enable updating links – but I think it’s an idea worth stealing.
  • Will it change anything? The biggest known unknown for me right now is roughly “how will things change now that I’ve written a book?” and my best guess is that things probably won’t change much – which is great, things are going well already. I’m curious to find out whether I’m underestimating things.

Ah, I’m sure there is a bunch more, but that seems like a good start.

Altogether, if you’re considering writing a book, I’d really recommend giving it a go. I don’t know many folks who are interested in writing a second book, but I don’t know any folks who regret having written their first.

Personally, I'm certain that I'd like to write another book at some point, but right now it's hard to imagine having the energy to do all the parts around writing the book again!