How I Wrote My Book
I recently shared my journey to landing my book deal with PublicAffairs Books, a division of the Hachette Book Group. But while landing a deal is an important piece of the publishing puzzle, it’s truly just the beginning of the book writing process.
Whether you pursue a traditional publisher or opt to self-publish, the creative process of writing an entire book is equally if not more challenging. So today I wanted to share the key strategies that helped me tap out over 65,000 words for my book.
The Big Idea
When I first launched Bossed Up, I set out to start a training business – a community where practical, research-driven training programs – like Bossed Up Bootcamp – would help women accelerate their lives and careers in a sustainable way.
I didn’t consider writing to be anything more than an avenue through which to market Bossed Up’s programs and share my ideas about helping women strive for sustainable success. So you can imagine my surprise when an early blog post of mine (originally written for my friend’s blog focused on gendered roles, RoleReboot.org, then republished by The Huffington Post) went pseudo-viral.
It was a short piece about how I caught myself at times playing up my hot mess-ness, especially around guys I was interested in, and how I wished it was considered just as sexy for women to get our sh*t together and own our power over our own lives.
It did so well, it served as early validation for my infant startup, and earned me some much-appreciated attention on the brink of debuting our first-ever Bossed Up Bootcamp – exactly as I’d hoped.
But I hadn’t counted on people in the publishing world noticing. In a stroke of luck, the piece had impressed an editor at Hachette and they invited me out to lunch to talk about writing a book. I was deeply flattered, but had no idea what to write about. After all, I was on the brink of asking big questions about women, work-life balance, and relationships. I didn’t have any answers to share yet!
Not to mention, I had no idea how to make a living doing this kind of work just yet! So I simply kept in touch with that editor and started toying with the idea of a what Bossed Up the book might entail. I also devoted the next few years to honing my craft. I learned a ton through organizing Bossed Up Bootcamps and interacting with thousands of women navigating career transition. And I improved my writing through years of practice, blogging, pitching guest pieces to different publications, and ultimately to writing a leadership column for Forbes.
All the while, the Bossed Up Book idea was becoming more clear, and I was feeling more and more motivated to make it a reality. I knew that I wanted to write a practical guide for women who wanted to get Bossed Up, but in the midst of running a busy, fledgling startup, I couldn’t imagine how I could afford the time to spare. Keeping Bossed Up afloat was a full-time job, How on earth could I write a book without my business falling apart?
The (Failed) Proposals
If I didn’t have time, I figured, perhaps I could earn some money to take time off to write the book. That’s what set me on the path to pursue a traditional publishing deal, which comes with a financial advance to supplement your income in order to take time to write your book’s manuscript.
But as I described in my interview with Colleen, the proposal-writing process didn’t work out for me. I tried working with two different book agents to write out a book proposal – essentially a business plan for the book – but the inspiration just wasn’t there.
By this point, the vision for the Bossed Up book was clear in my mind. So spending all this time writing page after page trying to explain the book instead of just writing it felt counter-productive to me.
Around this time I also read Elizabeth Gilbert’s Big Magic, a book all about embracing courage through creativity. In one passage, the book warned against ignoring your inspiration for too long:
…I’d seen this sort of thing before: The idea had grown tired of waiting, and it had left me. I could scarcely blame it. I had, after all, broken our contract. I’d promised to dedicate myself completely to Evelyn of the Amazon, and then I’d reneged on that promise. I hadn’t given the book a moment’s attention for more than two years. What was the idea supposed to do, sit around indefinitely while I ignored it? Maybe. Sometimes they do wait. Some exceedingly patience ideas might wait year, or even decades, for your attention. But other won’t, because each idea has a different nature. Would you sit around in a box for two years while your collaborator blew you off? Probably not.
pg. 47-48, Big Magic: Creative Living Beyond Fear, by Elizabeth Gilbert
That section got me motivated to cut to the chase and just write the damn thing. The proposal-writing process had dragged on for over a year, and by this point it was already 3 years past that initial lunch with the editor. She’d since moved on to a job at another publishing house, and I worried (rightfully so) that I wouldn’t get that lucky again. So I turned my attention away from winning a book deal, and instead focused on making the time to write.
Time v. Money
The trade-off of time versus money weighed heavily on me as an entrepreneur-author. It felt like a zero-sum game: I could either spend more time growing my business, or entertain this book-writing gamble, without the promise of a publishing deal at the end of that road.
Finally my cash flow was beginning to level out and become a little more predictable, so I felt confident that business was coming in reliably. When looking at the quarter ahead, I realized that I could afford to take a few weeks off in August to focus my attention entirely on writing. It helped that I had an absolute rockstar team in place – with Emi Kamemoto running our partnerships and Jackie Butler rocking out digital presence day-to-day – so I knew I could step away and the business I’d worked so hard to build wouldn’t fall apart.
Giving myself the privilege of time when I didn’t have the money (or a book deal) funding this writing endeavor was an absolutely key component to getting the Bossed Up Book out of my head and onto the page.
It just so happened that #BradTheBoo’s parents – who live on a farm in western New York state – were planning a trip in August as well, and were in search of a dog-sitter anyway. So I made the trip up from DC to their beautiful home, which has no internet access, making it the perfect place for a makeshift writer’s retreat.
I spent two weeks there, waking up, doing a few chores around the farm, and then planting myself on the front porch, where I’d clack away on my keyboard for at least 8 hours a day, 6 days a week. Two very non-glamorous weeks later, I had the basic structure of the Bossed Up book written – in a very rough draft form.
After those two weeks were up, it felt like my brain was mush and I was desperately in need of a real retreat, so I took my little sister on a 4-day section hike of the Long Trail in Vermont, to decompress and allow my brain some much-needed time in nature, not looking at screens all day.
I may not have had much money, but I had time. And truly, it made me feel like the wealthiest woman alive.
The next steps of writing the Bossed Up Book were some of the hardest, because it required the excruciatingly vulnerable process of letting other people read my half-baked book. And that’s truly what it was at the time – at just under 40,000 it was only slightly more than half of the 65,000 words the book would end up being. But you can’t make any book better without the power of editing and getting feedback – which in this case came in the form of a few early readers.
My first early reader was #BradTheBoo himself, who served as my psuedo-accountability buddy during my time on the farm, despite being back in DC. After completing my first draft of each chapter, I’d send share the Googledoc with him for his comments and feedback, which he’d leave in the form of conversation-starters and cheerful encouragement in the comments each night. He’d also often give himself credit by saying things like, “Hey, I’ve alway said that!” or “I taught you that!” to which I’d reply, “Yea, but I’m the one who wrote it down.”
My next early reader was Maria, a long-time member of the Bossed Up community, a Bootcamp alumna herself, and a friend. An attorney who’d navigated a career transition after burning out herself, we had a lot in common, and she offered to bring her word-smithing skills to help me in managing the initial editing process, chapter by chapter. I had 6 different chapters mapped out in 6 different Googledocs, all of which needed citations added, research done to fill in a few blanks, and thoughts fleshed out. It took about 3 months to finish the initial edit, at which point I was connected via a friend-of-a-friend to yetanother editor at Hachette.
When Colleen and I initially met up for drinks, we had an instant connection. It meant a lot to me that she was willing to really dig into my work and read through my draft manuscript early on – and go the extra mile to help me reverse-engineer my manuscript into a book proposal, so she could pitch the project to her entire team for review.
Allowing other people to see my early, unfinished, imperfect draft felt extremely vulnerable, but it was the most important accelerating force that propelled the book-writing process forward. I learned the importance of sharing your work early and often. Keeping it to close to the chest suffocates your art.
Re-Writing and Editing
By the very end of December 2018, with the final book deal in hand, I knew I had a lot more work to do in the new year. Plus, now I was on deadline – a contractually stipulated deadline. To reach my 65,000 word count minimum, I knew I had more to say about the science of burnout and the history behind what I call the martyrdom mindset, and I also knew I wanted to add a meaningful introduction and conclusion chapter. But more than anything else, the book was missing some much-needed personal stories.
Since I’m always profiling and featuring inspiring members of our Bossed Up community, I knew right away that I wanted to add some concrete examples to each chapter from real women who were living it! I knew of so many Bossed Up Bootcamp alums who were walking the walk in terms of getting bossed up, so I spent the next 6 months interviewing and writing up their stories, getting the subject’s feedback, and finalizing my second “final” draft of my manuscript
Without the ability to take a concentrated amount of time away from running the business to focus exclusively on writing, I instead inserted “writing days” into my regular work week. I blocked off Tuesdays and Thursdays when I wasn’t traveling for speaking to focus on writing only. I’ll admit: it didn’t always work, and it did require putting a few other projects on the back burner for the short term, but it enabled me to hit my deadline without issue. On the last day of June 2018, I turned in my final manuscript, and for about a month, the project was out of my hands and solely on the desk of my editor, Colleen.
It was a good thing, too, because at that point, my attention turned towards my wedding, which was less than two months away on August 18, 2018, and we had a LOT to plan for! We hosted the wedding back on the boo’s family farm and I spent every spare moment of time I had in the following month and a half preparing for it and basking in all the love that celebration entailed.
Once home from the two blissful weeks that Brad and I took off to get hitched, however, I spent the next two months working through line-by-line edits Colleen had left for me. We went back and forth making tweaks, strengthening arguments, and re-reading that damn manuscript until I thought my eyes were going to be permanently crossed. It was an arduous, frustrating, and somewhat boring process, but it left me feeling like we’d been sculpting a smooth statue. It had started off rough and abstract, but through reading and re-reading, writing and re-writing, we chiseled that baby down to a masterpiece.
I thought surely, we had to be done at this point, right? But even after turning in my final edited manuscript towards the end of October 2018, we still had a ways to go.
Once the editing process was complete, the copy-editing began. I wasn’t familiar with copy-editors before writing the Bossed Up Book, but after working with the two brilliant women who copy-edited my book, I’m left convinced that they’re superhuman. These two grammar geeks went line-by-line with a fine-tooth comb, perfecting every last comma placement, creative capitalization, and spelling mistake I made. I fought them at times, and pushed back whenever the “grammatically correct” choice felt like it was detracting from the meaning, but their brilliance took my writing to the next level.
They double-checked all my citations and noted where my arguments would be strengthened by an additional note or resource. They confirmed every quotation was in fact accurate, and helped me ease up on my overuse of italics. What can I say, I meanwhat I say.
The very final editing came down to picking fonts, designing chapter headers, and finalizing the look and feel of section breaks and inserting featured graphics, designed by one of my long-time graphic designers, Ellie Nonemacher. I worked with Hachette’s in-house cover artist, who captured the vibe of the book perfectly in my cover art, and had the support of Colleen, my editor, in shepherding me through the process all the way.
- Writing a book is a long, arduous process. My book is just over a month away from being published, but it began as an idea spurred on by a lunch meeting I took in 2013, nearly 6 years ago.
- Many creative people made this process possible. I feel so fortunate to have had the help of many brilliant people along the way, many of whom are within my publishing house at Hachette, but also the early supporters who urged me on from the start.
- Answer the call, or the idea stops calling. More than anything, I’m so glad I dropped everything to write my first rough draft as it was bouncing around in my head after my book proposals failed. If I hadn’t answered the call and honored the idea then, I doubt I’d be able to write the same book now.
- Writing a book and selling a book are two very different things. Finally, I share all these lessons learned with the utmost humility, because I’m currently mired in a whole new adventure. Writing a book was a wonderful challenge, but figuring out how to get it into the hands of the thousands of badass women who could put it to good use is a whole different ball game.
Do you want to write a book someday?
What further questions do you have about the process? I’d love to hear from you and keep the conversation going in the comments section below.
And of course, I’d love your support in pre-ordering my book now and sharing this with the women in your world you think would benefit!
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