How “Dear Graduate” went from self-published to a traditional publishing deal

Is it possible to self-publish a book first, then solicit a traditional publisher? Sure, but only if your self-published book demonstrates a history of sales. If it doesn’t sell in a self-published format, you’ve proven to publishers that it’s not worthy of further investment.

In Build a Better Business Book I wrote about authors that made the leap, including Phil M. Jones with Exactly What To Say and James Fell with On This Day in History, Sh!t Went Down. I recently interviewed author Charles McEnerney about his book with Adam Larson, Dear Graduate: A Book for When We Take a Step Forward. This formerly self-published book for new graduates has just come out in a new edition from the Penguin Random House imprint Clarkson Potter. As you’ll see, it took a whole lot of work for the authors to get into a position to make that deal.

How Dear Graduate got a publishing deal

In the winter of 2021, Charles had two kids on the verge of graduating, one from college, and one from high school. He and his partner Adam began to have conversations with these young adults centered around open-ended questions about what they would like to do with their lives. Using Adam’s design skills and a local printer, they laid out a book and printed 1,000 copies. With the smart title “Dear Graduate,” it was a natural gift for young adults around graduation time. It was a perfect impulse buy. But getting those purchases meant getting in front of parents, grandparents, aunts, uncles and mentors. That meant being on tables and shelves in bookstores.

Reaching out to local bookstores near their Boston home by email, the authors managed to get around 30 bookstores to carry the book, about half on consignment. They would stock three to five copies per store. At a list price of $15.99, and counting the cost of mailing the books to the store, it was barely profitable, but the books were moving and the stores were reordering. The authors sold more than 500 books in the first year, about half through bookstores and half online.

For the following year, it was clear that Charles and Adam needed to get serious. They applied to get carried in Barnes & Noble, which turned them down. But they did manage to get listed on Ingram, allowing them to get books into a warehouse with an ordering system that any bookstore could use. They also found a new market: gift stores. Charles was able to identify a distributor called Faire that would make the book available to gift store buyers.

In the years that followed, the authors expanded to a broader collection of stores in New England and continued to build on the gift store channel nationally and internationally. The book was beginning to get some buzz around graduation season on Instagram. But both authors had full-time jobs, so operating a book fulfillment business on the side was getting to be a lot of work. They’d proven the book’s appeal and had sold 3,000 copies with smart marketing and a lot of persistence in a fragmented bookstore channel. Bookstores and gift stores were ordering books by the dozen. Would a real publisher become interested enough to pay an advance and take over the printing and distribution?

Charles began outreach to agents. It took many months, but one agent, Kristin van Ogtrop of InkWell Management, the former editor of Real Simple magazine, saw the potential and managed to interest the publisher Clarkson Potter. Given the proven appeal of the book, Clarkson Potter offered a modest advance and a fair royalty deal (the publisher’s site for the book is here). Charles has continued to use social channels to build audience for the book and drive sales through the 2025 graduation season, the first in which the book is available from the new publisher.

Like any good author, Charles is not settling for writing one book. Graduation is clearly not the only life event when people ought to be asking themselves questions about who they are and who they are becoming. But he and Adam won’t need to bootstrap their way for the next book; they have a publisher and a track record, and that’s a pretty good start on succeeding with a traditional publishing deal for the next book (or six).

What Charles did with Dear Graduate was impressive — and pretty hard to duplicate

The nonfiction authors I work with generally pursue national visibility. Their market is narrow but geographically widespread, for example, digital marketers or heads of HR for companies with 100-500 employees. Such a focused audience is a great way to build thought leadership, but makes it challenging to make the leap from a self-published book to a traditional publisher. Unless you can show that your self-published book has sold at least 10,000 copies (or is on a path to do so), the publisher has little incentive to take a risk on you.

Charles and Adam’s outreach to bookstores was the right approach for a book focused on impulse buys and perfect for one timed to a specific season, graduation season. Even so, it took a lot of effort to sign up independent stores one by one. Luckily for them, the book resonated with both bookstores and buyers seeking graduation presents, so the outreach eventually paid off.

I’d love to hear about more “Hey, I have to have this book”-type successes like Dear Graduate. Are you the author of a self-published book that resonates with book buyers? How do you get traction? And have you turned that into a traditional publishing contract, or are you happy on the self-published path?