The Writing-in-Public Story of Deploy Empathy

A bunch of people have asked me about the writing-in-public process for Deploy Empathy, so I thought I would take a few moments to get it all down while it’s still fresh.

The genesis for the book came from conversations I’ve been having with founders over the past few years. From listening to my podcast and various talks I’ve done, people know that customer interviews are my favorite topic, and would often come to me for advice on starting their own customer research efforts. I had calls about this every so often for a few years, from Calm Company Fund founders to random people who DMed me on Twitter.

It wasn’t until I started mentoring a sprint group for Founder Summit last fall that I realized how jumbled my “further resources” recommendations were. It was a mix of blog posts, book chapters, podcasts, and other resources, many of which were only partly relevant to people starting or running small software companies. With the exception of The Mom Test, most of the resources out there assume you have resources at your disposal or are written for UX researchers or product managers rather than founders. As a result, my recommendations were caveated with things like “only read the middle third of this book” or “this book is written for people in big companies so only read chapters 2, 3, 4 and don’t get discouraged when they talk about budgets and resources” and I would have to write a whole bunch of extra things about stuff that wasn’t covered in existing books.

By February, I had the idea of writing a book in my head:

But the idea also terrified me. I’d heard writer after writer talk about how lonely writing a book is. We were in the middle of a strict lockdown and the last thing I needed was more loneliness in my life. I briefly considered going the publisher route, but quickly ruled that out after hearing about experiences others have had (thank you, Paul Jarvis and Alan Bradburne for sharing your perspectives with me).

I decided if I was going to write a book, it would be on my own terms.

It would be social. I would absolutely not be locking myself in a room for three hours every morning until I finished. It would be as I felt inspired. No publisher lording over me with the rejection-filled querying process, deadlines, an advance to pay back, or book tour stops. No pressure on myself to create a book.

So I decided to take the plunge on doing things “in public” and decided to write in public. When I started out, I wanted to put as little pressure on myself as possible (see: lockdown, painful, didn’t need more stress, needed fun). I mentioned in the first issue that it might become a book, but moreso I told myself I was simply creating a collection of resources that would be useful for me the next time someone reached out about how to do customer research. Instead of having a call, which has become inconvenient due to timezones and was then impossible due to lockdown, I could simply send people to the newsletter archive, trusting that they were in safe hands (my own) and would have everything they needed to get started.

So in many ways, the newsletter was solving my own problem: my own problem of having a place to send people when they had questions. And maybe at some point I would roll all of the newsletter issues into a free PDF and call the entire effort a day.

I started writing issues as the topic struck me. I didn’t write them in any particular order, on any particular schedule, and I didn’t edit any of the issues before I sent them out. (Thank you to Joel Hooks for encouragement on that one.)

The lack of editing was hugely helpful for momentum and enjoyment. In the past, when I wrote blog posts, I would fret over them for weeks and often enlist a friend or two to edit them for me beforehand. I’m grateful for those friends who edited my post. Yet this whole process taught me that for me, bringing in another opinion besides my own makes the process stressful for me. I’ve realized that I don’t do well in situations that require me to impress others. It’s bad for my mental health and I hate it the whole time it’s happening. It’s one reason why I never applied for prestige consulting jobs after college, considered raising venture capital, or wanted to get a publishing deal. I phrase this to myself as “I don’t do beauty contests” (which is what these sorts of processes feel like to me) and in some ways, the early editing process when a piece of writing is still a little baby chick that needs nurturing and support also puts me in that mindset.

So, no beauty contests. No editing before the posts went out. (That came later.)

I also didn’t write for an audience. In the past, I wrote my blog posts for a nebulous audience that usually ended up being an audience of five people when the post landed with a thud. I would get too much in my head about what I was writing and who it was for. This led to writing that was confused and not very compelling. Instead, when writing the newsletter, I told myself I was simply writing emails to one person: my co-host, Colleen. Colleen is someone I respect and consider an equal, and I simply told myself I was writing to her when I was writing. This made my writing conversational, and avoided any issues I might have with trying to write simply (which can be accidentally condescending) or convolutedly (when trying to impress).

“I’m just writing emails to a friend that will happen to be public on the internet,” I told myself. “I’m not writing a book, just writing emails.” I write a million emails a day, so this de-stressed the process for me. And I happily banged out sections for a few months after that, writing them whenever I had a spare moment. I would often crawl into bed at night with my laptop and write them as a reward after a long day of lockdown parenting/working.

Throughout the process, I was intensely worried that I was writing a book that already existed. I needed to answer for myself whether my writing was suitably unique enough to consider rolling into a book. This meant I plunged into my library of books on jobs to be done, user research, negotiations, and empathy. It was an unexpectedly soul-nourishing part of the process to get to dive back into some favorite books and read a few new ones.

By April I had finished most of my re-reading and the majority of the newsletter issues, and was starting to get more and more messages like this:

I was still unsure on whether it should become a real book (like a paperback buyable on Amazon, which it is) or just a PDF rollup of the blog posts, so I decided to interview as many of my newsletter readers as I could to understand how they were using the newsletter issues and what their workflow for learning professional skills looked like:

I ended up interviewing over 30 people in the span of two weeks, which was both an exhausting whirlwind and absolutely delightful. I talked to people from New York to Australia, Japan to Romania, Ottawa to Singapore. It was amazing and so soul-nourishing to talk to people around the world who were passionate about the same topic as me and who I had helped. I thought I might be helping them but to hear someone say on a call that I had helped them was magical.

Inspired, I then got to work compiling the first draft. Arvid Kahl put me in touch with Help This Book, a book-in-public platform from Rob Fitzpatrick, writer of The Mom Test. That platform and Rob’s new book, Write Useful Books, were hugely helpful to me. I sent out an ask for alpha readers on April 20, and opened it up to more people a few days later. In that same burst, I wrote a bunch of newsletter issues -- the last remaining topics from my original mental list. People started leaving me really helpful feedback on Help This Book with lots of comments about what worked and what needed to be reworked.

And then I didn’t touch it, any of it, for about two weeks. I needed complete distance from it, and I had zero desire to look at the draft or think about it.

I returned to the draft in mid-May, and commenced what felt like weekly major rewrites of the entire draft. I was moving chapters around, adding sections, deleting sections constantly. Mid-May through the end of June was the most intense writing process, and the most exhausting. I devoted much more of my time to the book here; I probably did about 30 hours of book work a week at this time, as opposed to 3-5 hours per week for February-April (excluding the interview weeks at the end of April).

May-June was writing in public and also struggling in public, and somehow, that made it bearable. It was incredibly frustrating, yet it was still a social process. From anonymous newsletter readers commenting on the Help This Book versions to friends giving me honest feedback on drafts, I never felt alone in my struggle, and I am so grateful for that. People kept cheering me on with encouragement and suggestions.

Around this time, I also started thinking about getting reviews for the book from readers and for the cover. I have no illusions about customer research and am aware it’s a vitamin rather than a painkiller (though perhaps the gummy kind that people don’t mind taking), so I knew I would need lots of social proof to convince people that customer research was worth the effort. I DMed everyone who had tweeted positive things about the newsletter/book (what was it at that stage, really?) and a few people I interviewed who had been particularly effusive for testimonials.

I also knew I would need quotes for the cover to lend credibility and credence for people who had not followed along with the process. This was the most nerve-wracking part of the entire writing process. I reached out to a few people I knew personally and two authors with related books in the space. Two people, Morgan Housel and Patrick McKenzie, said they would be happy to write reviews (yes!), but the authors ended up declining, one immediately and one several months later, and admittedly, both felt like a punch in the gut. (I respect their reasons for doing so and understand it didn’t have to do with me personally, but there’s the honest truth, and that’s the whole point of writing this up: to give you an honest look at the writing process.) I dusted myself off and reminded myself of my immense gratitude and appreciation for Morgan and Patrick. I will be forever grateful to them for that.

I finally threw up a simple website and [opened the book up for pre-order on June 2nd after the gentle prodding of Sean Fioritto and Gabriel Chuan:

It was downright scary—was what I wrote really worth paying for? It wasn’t even done yet!—but I had learned from various build-in-public people like Sean and Shawn Wang that I needed to get one out there and I needed to do it sooner than later. (This feels like a good moment to give a special thanks to Sean Fiorrito, Shawn Wang, Alex Hillman, and Arvid Kahl, conversations with all of whom helped me figure out what exactly the write-in-public process looks like at a nitty-gritty level.)

To my complete surprise, five people bought it, and a bunch of people tweeted about it, and we were off to the races. To someone who previously fretted over blog posts to only have them go nowhere (see discussion of my thuds above), it was—and honestly, still is—a bewildering surprise that people want to read nevermind pay for what I’ve written. My brain still doesn’t really understand it, but I decided to put that aside and just roll with it.

I struggled with knowing when the book was done.

As a recovering perfectionist, I knew that I would have to just call it done at some point, because otherwise I would just keep fussing over it and never release it.

It wasn’t until someone I didn’t know -- someone who hadn’t been listening to my podcast or reading the newsletter -- commented on a friend’s post about it that they had bought the book and said it was making them rethink their interactions with customers and co-workers that I knew it had done what I had set out to do. My goal was never just to give people scripts for interviews. For me, it has also been about helping people discover how to be more empathetic in all of their interactions, not just with customers. Hearing from a complete stranger that the book had prompted them to do that was what I needed to hear to convince me that the book had done what I set out to do.

I set a deadline of June 28 (our daughter’s last day of school before summer and thus my last full normal workday for six weeks), and the writing process intensified. I took down the Help This Book version once I ordered the pre-sale and went back to writing in Google Docs. My volunteer editors and I continued ripping the book apart and re-assembling it, and I ended up uploading four new versions to the pre-order. I moved the copy to Vellum for book formatting and in mid-June, I contracted a professional proofreader via Reedsy. (If I were doing this again, I’d wait to import to Vellum until after proofreading were complete, as that made things a bit complicated.) I also started working on the mechanics of publishing a book, like buying ISBN numbers and a barcode.

By early July, the content of the book was effectively done. And my expenses were piling up.

I knew I had to market the book, and I knew I needed to make it more accessible. A bunch of people said they were waiting for a paperback version, so I set to work on making it available via Amazon Kindle Direct Publishing, which prints books as they are ordered. This is a huge improvement over the self-publishing of years past which required the indie author to both publish and distribute their own book.

But first, it needed a cover.

Damien Terwagne, someone who had been part of my cheerleading squad during the newsletter-as-rough-draft stage, had offered to create the cover several months beforehand, and it was at this point that I took him up on it. He offered to do it for free, but that didn’t feel right to me, so we came up with a deal:

He would do the cover and I would do 1 hour of free consulting for his own company, Dawn, and a $100 donation to a charity of his choosing (the Child Mind Institute). A friend suggested that the “picture yourself as a rubber duck” might be an effective cover and visual reminder of how someone should comport themselves in an interview, so we decided to go a little whacky with the cover and put a rubber duck on it. (If you’re wondering yourself, the answer is in Chapter 37.)

By the end of July, the cover was done, and I was ready to upload everything to Amazon. Amazon’s review can take up to 72 hours, so I uploaded it on Friday the 23rd, and we went out to dinner to celebrate. I checked it on Sunday and there it was, available for purchase:

I wanted to order proof copies before telling people about it, but I was just way too excited and in shock. I tweeted it out, and even though I told people not to buy it because I hadn’t seen it myself, people started buying anyway. (I love you.) On July 26th, I got photo evidence of the first physical copy, and it really started to hit me:

I wrote a book. I wrote a book? I WROTE a BOOK?! I wrote a book. I wrote a book!

I wrote a book.

And after that sunk in, my husband said to me, “You realize this is just the beginning, right?” And right he was. The writing process was just step one, and now to market it. The book hit #1 on Product Hunt last week, which was an absolute roller-coaster and completely surreal to have so many people around the world lifting up my work.

I’m doing a virtual book tour (first stop was on Searching for SaaS) to promote it. Colleen has challenged me to do 20 stops over the next six months, so stay tuned to see if I hit that goal :)

If you’re considering writing your own book, I hope this was helpful. If you followed along with the process, I hope you enjoyed this look back. I’m so grateful for everyone who helped and cheered me on and supported me throughout this whole process.

I’m happy to take any questions or comments you may have :)