The Spirit-Crushing, "No"
About six years ago, I got a little obsessed with the idea of writing a business book about the business case behind a certain leadership team that I really admired. I put in somewhere between 50-100 hours of my time coming up with a book proposal to flesh out the concept. To supplement the proposal, I conducted some interviews of my own, along with some outside research and a competitive analysis on similar books.
I even got a literary agent interested in workshopping the idea with me to really help me bring it to life and I got pretty precious about the concept and the story itself. There was just one problem: I wanted journalistic access to my subjects in question. And for that, I needed permission.
I sought out a peer collaborator, who helped me get a meeting with the person in question. I was granted fifteen minutes and during that time, I was told, “No” more times in fifteen minutes than I thought was possible. I proposed countless new angles, approaches, or ideas, but the answer was always the same: Not right now. Not like that. Not ever. Just…no.
I was totally crushed. I could not understand how to move forward. And I all but shelved the idea.
When Rejection is a Good Thing
Last year, while I hadn't really planned on it, I happened to pull together the content for a different book, one on fractional work best practices as a guide for the solo-preneur, so to speak. I called it, Go Solo. In the course of one week, with the help of AI as my boost, I not only finished a pretty decent first draft, but got the book in publishable shape with an AI-powered design tool. It netted out at about 25,000 words, a short but jam-packed piece of content.
After I finished this draft, I asked myself, “Now what? Do I self-publish this on my own? Put it up on Gumroad? Or try to convert it into a legit printed book?”
I thought back to some of the conversations I’d had with that literary agent six years ago and decided to explore the possibility of interest in my newly workshopped piece. Unlike last time, I skipped through all of the steps of formally writing a book proposal, I didn’t bother with the competitive analysis or the framing. I dropped her a note and told her I’d be dropping off something for her review and consideration. After miraculously talking my way up into a high-rise office building (where I was definitely not on the security list), I was able to get a printed copy of the book on her desk.
About a week later, I received a response that indicated, essentially:
Come back when you’re serious and put in the time to make a formal book proposal.
Any AI-generated material will make this book a non-starter for any of the big 5 publishers.
When I saw this email, I laughed out loud. The idea of removing AI-generated material from a book that I wrote and designed with AI, about how AI makes fractional workers like me into supercharged versions of themselves was simply not an option.
While I’m sure there is still a market for books like this, I knew that slowing down my own hyper-optimized workflow by months (if not years) to spread the word about my fractional journey would actually worsen, not improve, the end product.
But here’s the difference: Unlike the rejection from before, this time, I was not crushed at all; I was relieved.
I took one look at that email and thought to myself, “Well, I guess traditional book publishing is completely off the table for me now. What else can I do?”
That thought spiraled into a myriad of other more AI-native content remixing options. Things like repurposing my own content on my blog, converting ideas into videos, coursework, and even more things I haven't explored yet but know will become increasingly relevant and exciting in an AI-native world of self-publishing.
In today’s fast-moving, uncertain world of work—and life in general—I’ve started to intentionally push the boundaries of where I might hit a "rejection point." Over the past 18 months, I’ve been rejected more times than ever before—by individuals, on project work, and even for jobs I’ve pursued. And yet, I’ve come to appreciate that you often learn far more from a direct "no" than from an easy "yes." It’s nice now to see that maybe it's not rejection—it’s an injection of a new possibility or framework.
After all, in the span of a single email, she saved me hundreds if not thousands of hours of wasted effort. That is the power of a good rejection.
