What I Wish I Knew Before Writing a Book
I’ve been reflecting on what I learned writing two business books and wanted to share those insights that I wish someone had shared with me before I started. Escaping the Build Trap has sold over 75,000 copies in 5 years, and my second book Product Operations came out just a few months ago. If you're considering writing a business book, here are some of the biggest lessons I've learned that might help you.
Know What You Want to Say Before You Begin
Writing a book really boils down to caring deeply about what you're trying to say. Back when I was gearing up to write "Escaping the Build Trap," I bumped into a publisher who was keen on me penning a book about Agile UX. But my heart was set on Product Management. They brushed it off, saying, "Look, the world's got enough books on that topic." That was back in 2016. I wasn't buying it, though. If we'd really covered all there was to cover on Product Management, why were folks clamoring for more of my blog posts? Why was I getting invited to speak at conferences left and right? I was getting all this feedback that people needed to hear what I had to say, but that publisher just couldn't see it. O'Reilly did, though, and that's who I ended up going with.
So, before you dive in, make sure you're clear on your message and your audience. Test the waters with conference talks, blog away, throw your thoughts out on social media. See how people react. If there's a spark of interest, you've got something. Build your audience before you start writing. And once you start, hold on to your beliefs.
Question Why You’re Writing a Book
Think about why you want to write a book and the difference you hope it'll make. I wrote "Escaping the Build Trap" for a bunch of reasons. I love doing things that reach a lot of people. My aim was to wrap up my thoughts on Product Management into something solid I could share far and wide. Sure, I was getting the word out through talks, teaching, and consulting, but there's only so many folks and companies I can help face-to-face. The number of people asking for my help started to be more than I could handle. A book seemed like the best way to spread my ideas, especially since there wasn't anything out there tackling the exact problems I wanted to talk about. I'm all about teaching and helping others, and I wanted to do that on a bigger scale. That's also why I teamed up with Denise to write "Product Operations"—to reach even more people and make an impact.
Another reason I wrote "Escaping the Build Trap" was to up my credibility. Back in the day, if you were a consultant or speaker and wanted to get noticed, you needed a book with a publisher's name on it. Even with all my consulting and speaking, I was missing out on the top keynote spots and the best consulting gigs. So, I decided to write a book. Now, I'm not so sure that's how it works anymore. Things seem to have changed lately. By the time I finished "Escaping the Build Trap," my credibility was already on the up, even without a book out there. Looking back, the book has helped, but I do wonder how things have changed now with LinkedIn articles and podcasts popping up everywhere.
Let's get one thing straight—I didn't write these books thinking I'd make a ton of cash. Writing a book isn't a shortcut to getting rich, and you shouldn't count on a windfall unless you're a big name with tons of fans. For more on this, take a look at the bit about The Publishing Paradox.
The Writing Process
When I first tackled writing "Escaping the Build Trap," I didn't have a clue about book writing. I chatted with friends who were seasoned authors, and they threw a ton of advice at me: write for an hour each morning, sketch out a detailed outline then flesh it out bit by bit, or take a few months off and just hammer it out. But with a full consulting schedule, I couldn't just hit pause—this book was going to be a nights and weekends kind of project.
For months, I was stuck on how to even start. That's when I brought in a developmental editor, Bridgett, who was a godsend. Structuring my thoughts and figuring out the flow were my biggest hurdles. Bridgett walked me through it all, from outlining to the nitty-gritty of writing. Whenever I hit a wall, we'd talk it out, record our chats, and she'd draft up a chapter. I'd get her draft, react, and end up reworking it. It didn't have to be perfect on the first go—the key was it got me past that intimidating blank page. And when something wasn't clear, she'd call me out, which was priceless.
I thought I'd zip through the book in six months. It took two years. Writing down your ideas is a whole different beast compared to giving talks or running workshops. There's no room for on-the-spot explanations or Q&As. I had to keep reassessing how I presented my ideas, really digging into my own understanding. Plus, I was putting these concepts into practice during a major product management overhaul at athenahealth. Sometimes, I'd write something, try it out, and get thrown a curveball. Back to the drawing board I went, and that chapter got a rewrite. This hands-on approach really put the book through its paces.
For my second book, I teamed up with Denise Tilles as my co-author. We skipped the developmental editor this time because I had a better grip on structure. Laying out the framework was a breeze. We'd toss drafts back and forth, constantly reworking them. Whenever we got stuck or questioned our explanations, we'd hash it out together. This collaboration made the process smoother, though not any quicker—we still took two years. But I'm convinced the book was all the better for it. Plus, having Denise meant we kept each other on track, pushing each other to get things done.
Writing daily is a struggle for me. I need to hit that flow state. When I'm in the zone, I can write for hours on end. Other times, I can't even bear to glance at the manuscript for weeks.
Here's the thing: don't just go with the flow of popular advice. Carve out your own writing path and cut yourself some slack. Writing a book is a marathon, and once it's out there, it's not like you can easily tweak it. Take the time to polish it—make sure it's a book you're proud of.
The Publishing Paradox
Deciding whether to go with a traditional publisher or to self-publish is a big choice that'll stick with you. I went the traditional route for my book "Escaping the Build Trap," but when it came time for "Product Operations," my colleague Denise and I decided to self-publish. Here's my take on the good and bad of each.
Traditional Publishing:
Pros:
They handle the heavy lifting on compiling the book for print and distribution: design, layout, and sales are all taken care of.
A publisher's name can give your book some extra clout, depending on the publisher.
You don't have to sweat the legal stuff like copyrights.
They sort out distribution and translation contracts, and deal with any rights issues.
Sometimes they give you an advance, which is handy if you need to take time off to write, but don't expect a fortune.
Cons:
Don't expect much help with marketing; you'll need to hustle on your own. Publishers only help with marketing the absolute top books by celebrities. For a business book, you need to have a plan of your own on how you will get it into people’s hands. Otherwise, it will fail.
Royalties are pretty slim. I get 10% for "Escaping the Build Trap" paperbacks and 50% for the digital version. For translations and audiobooks, it's even less.
You give up control. Want an audiobook or a translation? That's up to them, not you. You assign the copyright to them, forever (or so long as they keep printing it). I fought for an audiobook for years, and I had no idea it was licensed to someone until the audiobook came out. I would have liked to read it, but I was not given a choice.
Getting your book into stores isn't a given. Publishers focus on their bestsellers when it comes to any marketing or pushing to get it stocked in stores.
You have to buy your own book. If I want any copies of "Escaping the Build Trap", I pay 50% off the cover price. I do not control the cover price, so it’s usually cheaper for me to buy my own book on Amazon.
Bulk orders? You're at the mercy of the publisher's prices and schedules, which can be a pain for events.
Self-Publishing
Pros:
You call the shots on your content and copyright. You can make any derivatives you would like.
Set your own price and change it whenever you like.
Buy your book at cost and handle your own bulk deals.
You decide on distribution, translations, and audiobooks.
The book's look and feel? Your decision.
Cons:
You've got to pay out of pocket for design, editing, and all that jazz. We made back all the upfront costs we spent on Product Operations on our first day of sales, but it still required cash up front.
You still have to pay royalties to KDP if you go through Amazon, but it’s less than traditional publishers. This still feels unfair though. Amazon has a monopoly on self-publishing.
Printing can be a headache. There are only really two big players - KDP and IngramSpark. Quality control can be hit or miss, and you have no options over this. They are also both hard to deal with.
You're the boss, which means you're also the customer service department. So make time to deal with any issues.
For "Product Operations," I chose self-publishing because I wanted more control and flexibility. Dealing with quality issues is a headache, but owning my work was worth it. And hey, I know folks who've had quality problems with big publishers too.
If you're leaning towards a publisher, go for it! Just make sure you fight for a fair deal in your contract. Looking back, I wish I'd pushed harder. When I asked around, everyone said, "That's just how it is with publishers." Turns out, a lot of us have the same story. Most publishers play by the same rules.
The Value of Early Readers
Getting feedback early on is a game-changer. When I was working on "Escaping the Build Trap," O'Reilly sent out drafts to a bunch of readers, and boy, did their comments shake things up. They led to a total overhaul. You see, the whole Marketly story in the book? That wasn't even a thing until those early readers chimed in. I dug into nearly 500 comments—yeah, they didn't hold back—and it hit me: the book was missing a common thread to tie everything together. So, I buckled down, dreamed up Marketly, and hammered out a whole new draft in just two months. That kind of pivot? It wouldn't have happened without that early feedback.
The same thing happened with my book "Product Operations." Thankfully, by then, I had a better grip on how to structure a book, so I kicked things off with a story right from the get-go. That meant the rewrite wasn't nearly as massive.
Here's the thing about criticism: be open to it, really dig into it, and let it make your work better. But also, know what to take on board and what to let slide. People will always have their two cents to throw in. Get where they're coming from, but if something doesn't sit right with you, trust your gut. You don't have to act on every piece of feedback you get.
Writing a business book is a huge task, but honestly, it's one of the most fulfilling things I've ever done. I still get a bit choked up when folks tell me my books made a difference for them. There's nothing like the feeling of creating something that truly helps others. I hope this gives you a bit of insight to figure out if you're ready to dive in yourself. And keep in mind, books aren't the only way to spread your ideas. Choose what fits you best.
I’m always thankful if someone wants to buy my books! You can get them on Amazon, iBooks, Nook, or order through your local book store. Here are the Amazon Links:
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