Why I Wrote a Book (And What I Learned Building a Publishing Business)

A meta topic to finish the first run of newsletters before I take a summer break

Chicago, USA, June 2025 - Photo by Kevin Goldsmith

This will be the last new newsletter until September. I’m going to take a break over the summer and come back with some fresh, non-book-related content. While I’m off, I plan to re-share some of the more popular articles from the last eighteen months for your summer (or winter) reading.

Upcoming Talks

I’m going to give the keynote talk at Seattle’s Got Tech, which is part of Seattle Tech Week on July 30th in Seattle (obviously). I will also be speaking once again at the LeadDev conference in October in New York City.

Why I Wrote a Book (And What I Learned Building a Publishing Business)

Fair warning: this is going to be a bit long and detailed. If you're not interested in the mechanics of book publishing or starting creative businesses, feel free to skip this one. But if you've ever wondered what it's really like to write a book or are thinking about starting a DIY business venture, stick around. There are some lessons here that apply beyond just books. This is a condensed version of what I shared on the podcast last week. You can listen to that episode here.

Why I Wrote "It Depends"

I've been blogging about tech leadership since the mid-2000s when there wasn't much content available about transitioning from individual contributor to engineering manager. I'm not a super productive blogger – there are people in this space who write daily or weekly. I don't. But over a decade, you accumulate quite a bit of content.

The real catalyst was reading other people's books and getting increasingly frustrated. I'd read something and think, "Well, that's not really how that works," or "I can see why that worked for you in your specific situation, but this isn't a general solution." It's a common problem in business books generally, but it really irked me in tech leadership content. People would write very prescriptive advice based on limited experience, often after being in a role for just a year or two.

One thought that permeates almost all my writing is this: if I'm talking about something I did, I'm telling you it worked for me, but don't just do what I did. Take the pieces that make sense and use them in your way. I never tell you, "This is how you do a one-on-one" or "This is how performance reviews work everywhere." I understand why people like that direct approach, "Tell me what to do, and I'll do it," but I've seen too many times where the thing that worked before isn't working again, and you don't know any other way.

I'm constantly educating around the idea rather than being prescriptive. There are times when I've been more direct, usually when I'm in an environment where people are specifically looking for tools. Even then, I'll tell you to try it, iterate on it, and make it your own.

The other reason I waited so long to write a book is that I prefer not to write about anything until I've had time to understand it over time. That's where the real wisdom comes from. I'm always skeptical of books about executive leadership from someone who has only been an executive at one company or for a year or two. Unfortunately, there are a lot of those books.

The Self-Publishing Decision

I could have contacted established publishers. I know people at various tech publishing companies because I've blurbed other people's books and helped with reviews. My experience working with publishing companies suggested that they'd set high expectations around dates and content, want significant input, but also handle promotion and distribution. I wasn't sure I could deliver to those expectations as a first-time author with a busy job, even though having the structure and support would be helpful.

What I decided was that I wanted to understand what it takes to write and distribute a book. I wanted to learn the business, which comes from my Gen X DIY background. I've been a musician for forty years, and I've had my music distributed by other record labels, but my primary thing has always been a record label I started myself. I had to learn how the music business worked, including promotion, advertising, royalties, publishing, and copyright. While music and publishing have some differences, they have more similarities than you might expect.

I also felt comfortable knowing that the tools for self-publishing are now much easier to use. For this first book, which may or may not be successful, I decided to do it myself.

I'm also lucky to have a broad set of skills. I'm comfortable with graphic design, so I designed the book myself. A professional designer might have quibbles with how I did it, but I'm satisfied with the outcome. I recorded the audiobook myself using the same equipment I use for music. Having a professional recording studio in your home office is very handy.

Another reason I self-published was that if I ever decided to work with a traditional publisher, I'd come from a place of knowledge rather than ignorance, having to believe whatever they told me.

The Actual Mechanics

For the print book, I knew I wanted ebook, softcover, and hardcover options. Having run a record label with physical goods, I didn't want thousands of books in my garage forever, so I was interested in printing and drop-shipping one at a time. It's a little less convenient; you might wait longer than you're used to, but you do get it, and I don't have storage costs.

I used Amazon KDP and Ingram Spark. Using both was a challenge because Amazon really wants to be exclusive, and you get benefits by going only with Amazon. However, it was a reasonable tradeoff to be available in other physical and online bookstores, offering people alternatives to Amazon. Cory Doctorow's (https://craphound.com/) approach to self-publishing inspired me in this process.

Here's where I made a big first-time mistake: I thought having the book in a Word document meant I was ready to publish. That is not the case. I had to ingest the Word document into online tools and redo the layout four times – once for Ingram Spark, once for Amazon softcover, once for Amazon hardcover, and once for the Kindle store. This step took a tremendous amount of time.

The formatting didn't come through properly during ingestion, and I had to use their formatting tools, page by page. Worse, even though the book sizes were similar, they ended up with different page counts, so I had to update all the index page references four separate times. If I do this again, I'll work with someone who specializes in book layouts and pay them to provide print-ready documents.

For the audiobook, while I have experience with audio engineering, I'm a musician, not a singer, and I don't do a lot of speech editing. The last time I edited a recording of speech, I was using reel-to-reel tape with a razor blade. The tools are now much easier to use, but there was still a learning curve. I had to buy a pop filter because this was the first time I'd used my high-end microphone for voice recording. I spent a Christmas-to-New Year's week reading the entire book aloud, and by the end of each day, my voice was hoarse. You can hear that in the audiobook, along with the bit of a cold I had partway through.

I also tried using ChatGPT to generate an index, which seemed clever at the time (2023). I wrote Python code to ingest each chapter and generate possible index words in JSON format, then combined the indexes in Python and formatted them to be compatible with Word's indexing tools. I was really proud of this until I realized that the online publishing formatting tools ignored the generated index, and I had to rebuild the index by hand for each version of the book.

The Business Side

Once I had everything ready, I set a launch date and spent time building an audience beforehand. I started the podcast and newsletter in January to launch the book in March. I wanted time to create expectations. I guested on other podcasts, announced it at conferences, and worked to raise awareness through social media.

I also started running Google Ads, which was an educational experience. It's one thing to be familiar with SEO and SEM from managing teams that work on it; it's another thing entirely to build a Google ad campaign yourself. There are many ways to get it wrong, and I wasted money learning the hard way.

The nice thing about this DIY approach, especially today when you don't have to manufacture and store inventory, is that I started nearly every project with several thousand dollars in debt when I was running a record label. I'd have to make at least a thousand CDs and send 150 to radio stations and 150 to the press, so I was immediately out 30% of my copies plus shipping and production costs.

With the book, I spent very little upfront. I purchased subscriptions to the tools I needed, and once I started buying ads, I could choose how much to spend and adjust my budget based on what I was learning. The book was profitable within the first month, which meant I could then decide, month by month, how much more to invest in promotion.

How It's Going

It's gone well. I haven't sold a billion books or made a fortune, but I've sold way more than I expected to. I was prepared to sell five books and be done. Instead, I sell a few every week on average. Other authors in this space sell way more books than I do, but they also write more, speak more, and invest more in building their brand than I do. I'm happy with how I've done.

The royalty payments are low. If you buy the ebook for ten bucks, I get less than three dollars. You spend twenty on the hardcover; I also get less than three. That's Amazon taking their cut for printing and shipping, which I'm fine with. But if I'd gone with a well-known publisher, I'd be getting cents per book. I probably made significantly more money publishing myself than I would have through a well-known publisher.

Would I Do It Again?

Absolutely. The whole process was a lot of work: editing, preparing, recording, and promoting. However, I love having a physical representation that embodies who I am as a technology leader. The book feels great as a manifestation of that.

Will Larson, who's written some excellent books, has both self-published and gone through traditional publishers. He (https://lethain.com/more-publshing-thoughts/) wrote about his experiences with both, and he and I discussed it when we were both keynoting a conference. His experience was very similar – he did well with self-published books, but his royalties are way lower with the traditional publisher, and that book is probably less well-known than his self-published ones.

What I'd Do Differently

I didn't work as hard as I could have to get reviews. When I ran a record label, I built a massive mailing list of music publications worldwide by buying every magazine I'd never seen before, whether at record stores or when traveling. I could get twenty to forty reviews for any record I sent out. I didn't think to do this for the book, but I probably would next time.

I didn't do a book tour or arrange readings at bookstores. I might consider that next time or try to set up events when I'm traveling somewhere.

Next time I write a book, I won't be collecting blog posts – I'll be writing from scratch. I'll hire an editor because I'm not as good a writer as I'd want to be. I might hire somebody for book layout just because it was so time-consuming. I might seek help with promotion and ad campaigns because I likely wasted money by not understanding Google's tools.

I'd also do more social media promotion. If you follow me, you'll see one post a week about the podcast or newsletter, and that's about it. I didn't do YouTube videos beyond appearing on other people's podcasts. I struggle with self-promotion because if it feels too forced, I feel weird about it. But it would have helped.

The Bigger Picture

Even if you're not interested in writing a book, there are lessons here about starting any creative business. The ability to start small, test things, and scale based on what works is powerful. Not having to manufacture inventory or make huge upfront investments completely changes the risk profile.

The DIY approach let me learn the business while building it, which means I can make informed decisions about the next steps. Whether that's writing another book, working with a publisher, or doing something completely different, I'm coming from a place of knowledge rather than just hoping someone else knows what they're doing.

Additionally, I have this physical item now that might end up in a landfill or a library, and both of those options are acceptable to me.

If you're considering writing a book, starting a newsletter, launching a podcast, or building any creative business, please don't hesitate to reach out. I'm happy to share more specific details about the tools and processes or discuss the decision-making process further. Please send me a message at contact@itdependsbook.net or reach out on Blue Sky, Twitter, or LinkedIn. If you found this helpful, please share it with someone else who may benefit.

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