June 8, 2019.
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:
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.
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:
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!