Win With Flynn

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Frequent readers know that I’m close to completing my second book. A book I’ve been working on for the past year. It covers a topic that has intrigued me for quite some time: Trust.

The working title for much of that year was Trust Book: How to Grow It, and How to Blow It.

Most recently, I was working to find a developmental editor to collaborate on the project, now operating under the slightly more marketable name Shift to Trust. A business book, sure, but hopefully more.

It discusses the move from transactional relationships to something deeper—what I call uppercase TRUST. A framework for building trust that I’ve been chewing on since a war fighter from Fort Lewis looked me dead in the eye and asked, “Why the hell should I trust you?”

I didn’t have an answer on that day, but I do now, and that’s the book in a nutshell.

But you came here to learn about the editors, and learn you will.

I posted the project on Reedsy. Reedsy is like Monster.com or Fiverr, it is a marketplace to connect writers and editors. I attached an overview of the book, listed the areas I needed assistance, and included a sample of my introduction, about 3,000 words.

What happened next felt like some sort of cosmic joke.

For context, here’s what good looks like. One editor—Landon—wrote back to say he was fully booked and couldn’t take on new projects. A decline. A dead end. He wished me well and said I had a cool blog. He said he was more of a Phish fan than the Grateful Dead—a nod to a Deadhead case study I’d referenced in my project summary.

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Maybe he only read the summary. Maybe he never even clicked through to the blog. But he read enough to say something real, something specific, something that made me feel like a person and not a project number.

That decline connected more than any of the pitches I’d received.

And you know what? I’m definitely including Landon on my next editorial search. See how that works?

An editor, at least a developmental editor, is not just a human spell checker. They need to understand your voice. They need to see the frameworks, the structure, and the narrative arc not for what it is but for what it could be. They need to put themselves in the seat of the reader. What is confusing? What is unnecessary? What is vital?

The proposals came in. And every single one of them—from people whose entire professional identity is built around understanding voice, story, and human connection—sent me a form letter.

Not a bad form letter. A perfectly competent, professionally formatted, impressively thorough, generic form letter.

Bullet points. Deliverables. Credentials. Rate per word.

Not one of them mentioned my book. The sample. The ideas.

Every single proposal included a declaration—sometimes bolded, sometimes right at the top—that no AI would be used in this project. This was positioned as the differentiator, I suppose. The human touch. The proof that they actually cared, proof that they’d do the work, not Claude or Gemini.

And what did they send instead of AI-generated content?

Something so much worse. A slip sheet. A brochure. A flyer with their name at the top. The kind of thing you’d stuff in a folder at the trade show and throw away at the airport.

AI would have at least read the sample.

***

Let me introduce you to a few of the contestants.

Laura sent a thorough, well-organized proposal. Two rounds of edits, competitive pricing, good credentials. No mention of the manuscript, the subject matter, or any indication she’d read a single word. When I sent a follow-up asking for her initial thoughts on the sample, she replied asking if I’d already made a decision—and if not, she could “take another look.”

Take another look?

I’ve played that game before. It worked well in Mrs. Murphy’s seventh grade Language Arts. I told Laura I had not made a decision yet, and if she’d still be interested, I’d love to hear some initial thoughts. You know what she came back with?

Dinkus.

Yeah, dinkus. Now, that might sound like a pejorative. It might sound phallic. But it is a real piece of editing that should be considered. It is also super lame. Dinkus is, well, I’ll just show you…

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Dinkus: A generic typographic device used to mark a section or scene break. And while the term was new to me, and I thank Laura for introducing it, my use of dinkus does not show any understanding of the subject at hand. You could look at the page cross-eyed from 23 feet and see the dinkus. I need and want someone who will engage with the work, not the formatting.

Laura did not land the job.

Sarah had a Wharton Press background. Legitimate. Impressive, even. When I asked for specifics from her, she told me she “couldn’t provide detailed feedback at this stage” but wanted me to know she was “rejecting the majority of inquiries” and believed she could take my project “to the next level.”

Now, I’ll give you just a bit of a teaser, but the first stage in building trust, the jumping off point for my whole book, is transparency. That, she would have known, if only she had read the sample.

Instead, she used credentials. She used scarcity. She used tools of influence, not trust. She used twenty-five years of experience as a shield instead of engaging with the work.

Sarah did not land the job.

Despite my frustration, I still needed an editor, so I couldn’t quit on everyone.

I sent a simple question to all the editors that had responded with their SPAM.

“From your reading of the sample, do you see any structural challenges? And is there anything you’d want to know about the rest of the manuscript?”

No hints. No coaching. Just an open door. If they read it, did even one single thought flow through those big, highly credentialed brains?

The question was designed to do one thing: find out if anyone had even the shallowest thought about my book. A good answer didn’t have to be right. It just had to be specific. Show me you were inside the work, even for twenty minutes, and I’d be grateful and interested.

I was also looking for editors to self-select. If they read it, was it of any interest to them? Or were they just making a bid because they had time and a mortgage? I was looking for a collaborator that felt something, anything, about the book.

One editor—the one I hired—came back on a Saturday afternoon and said the subject of trust was a good one. That Stephen M.R. Covey deserves a lot of credit for the current material on this subject (I agree!), and that he had even interviewed Covey on this very topic. He asked for some time to sit with my sample and promised a response that Monday.

Of course!

On Monday he sent me three paragraphs breaking down the structural tension in the introduction. He mapped my own A→B framework back to me, identified where the logic didn’t close, and ended with this:

“A lack of a specific and unique core thesis is a lot harder to overcome—and that’s definitely not the problem here.”

He understood the work, he could see where it was going, he identified some potential pitfalls, and then, to close, he gave me hope. The Mary Poppins treatment. A spoonful of sugar.

God bless you, Chris. You are hired.

***

What I found interesting—outside of my prolific use of dinkus—the only pushback I received was from Chris.

He questioned whether my Story Grid approach was the right scaffolding for a nonfiction book that already had a clear framework. He emphasized the need for three acts, and the goal of walking readers towards the conclusion, where they will be delighted, because it will be both surprising and obvious. That is how you get an aha moment that sticks with someone.

He asked hard questions. He didn’t just tell me what I wanted to hear.

And that’s why I hired him.

There is an old saying that a problem well stated is a problem half solved. And for any editor that was interested in this project, all the clues were there for them, right in my request. Right in the question.

I’m writing a book on trust. The framework for building trust is in the sample. I also mentioned that my first book, Passing Notes to Strangers, was edited on Reedsy.

Now, I’m not expecting two edits for the price of one, and I realize they don’t have the time to read my sample and my first book just to land a gig, but any inquiring mind must have wondered, what is Passing Notes to Strangers all about?

Of course, because I wrote THE book on the subject, I’m a note passing psychopath. So I modeled good behavior.

When I reached out to the editors, I acknowledged their specific portfolios and proposals. I told them what I was looking for and why generic pitches weren’t helping me make a decision. I left space for them to respond without embarrassing themselves. I gave Laura a genuine second chance with a warm, specific, and if I do say so myself, funny message that basically handed her the answers.

I was, in other words, Passing Notes to Strangers like a boss. The idea that a single specific, personal note cuts through more noise than a thousand polished pitches.

The editor of Passing Notes to Strangers, Ray, won my business doing this very thing. His proposal had all the relevant information on his work product and pricing, but it had something even more important. He said he could see influences from Seth Godin and Steven Pressfield in my writing. My reaction? Yeah, that’s exactly what I’m going for. He understood what I was building before I had to explain it. That was it. He had me.

But in this case, the cobbler’s children have no shoes. The editors who help other people find their voice couldn’t find their own.

Copy, paste, send.

Delete.

Are these bad people? Bad editors? No, I don’t think so.

I think they’re freelancers running a volume game, and the volume game doesn’t reward the extra thirty minutes it takes to read a sample and write something real.

But that thirty minutes is exactly what connects perfect strangers. It’s what separates a transaction from a trusting tribe. It’s the difference between the marble in the jar mentality and real, lasting, trust.

To be fair, maybe I’m the strange one. It could be that other writers aren’t as precious about it. They just want to know availability, star rating, and cost. The editors are serving that customer, so I had to ask them to, you know, read my sample and have a thought about it.

But I can’t help it. When my first book came out, a friend sent the link to everyone we know. Someone on the thread had just had a baby, and he wrote, “Dave gave birth as well.”

It’s a book, man. It’s personal.

Chris starts soon. I’m excited to share what we create.

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