Make twice, sell twice

In November 2020, I independently published my first book at Gumroad. I had spent four months or so full-time deliberately researching, writing, editing, proofreading, and designing a PDF of ~18,000 words. That doesn’t sound like a lot of time, but you could say I spent most of the 2010s researching it (starting with this piece and the Prologue interviews).

The original book was a practical guide to creative endeavors, featuring 46 propositions, for anyone who considered themselves non-creative, but were interested in pursuing creativity either for their full-time job, side projects, or next career moves. I talk more about it with Chris Do at The Futur here, and you’ll find an excerpt at Fast Company here

There were a lot of reasons I went with Gumroad at that time. The main reason I chose it over Amazon: I wanted to keep my customer data, a lesson I’d learned from working with Ryan Leslie. I worked hard to promote my book; if they bought a copy, I wanted to be able to keep in touch with them and reach out to see how they were liking it, if I could support their learning experience, and with more of my work in the future

One of the main drawbacks to it was the reading experience: a PDF has all of the limitations of paper without any of the advantages of software. I was catching up with my friend Peter, who asked if there was a better way to take advantage of the digital format. 

Naturally, my mind jumped to a company called Holloway, a publisher who my former colleague Sean Blanda had mentioned. Holloway had made a solid reputation for itself, and it was a platform that promised a great digital reading experience. With Holloway, I could connect different ideas or parts of the book together (like an anchor link), beyond the linear top to bottom progression of a PDF. In Holloway, a footnote is actually just a hover link that shows more information—so instead of simply describing a subject as, “Visual artist Big Mike” I could write up “Big Mike” and present a short biography with him that does his work more justice.

Holloway had published a bunch of great guides, and I held their work in high esteem. So I reached out cold, submitted the manuscript, and heard back a week later. We worked out some business stuff, and by mid-May, I signed a deal to publish a new version of the book with them.

Throughout the months, we worked heavily on the positioning and title of the book (homework that I’d practically neglected the first time around). We worked together to come up with a new title, Creative Doing. The premise is that much of what we call “creative thinking” happens through action; the breakthroughs only come through us actually doing the work.

I also worked with Rachel Jepsen, the editor-at-large at Holloway (also a contributing editor at Every), to expand and revise the book from 46 to 75 prompts. Honestly, I didn’t really expect to expand it so much; I just decided to surrender to the process and take all the advice I got from Rachel, Josh (Holloway’s CEO), and the rest of the team.

For me, writing is fun, and editing is tough (even though I work as an editorial director!), but it was an incredibly rewarding process; the book is almost a completely different one, with a stronger structure, more substance, and greater clarity. (In some ways, the first version of the book feels like a mixtape, and Creative Doing (v2.0) is the true book. I’m not sure that I would’ve gotten here without writing and publishing that first mixtape though. The creative process can go on forever.)

There’s something of a meme on Twitter that goes like, “Make once, sell twice,” or “Build once, sell twice.” I’ve essentially done that, but the 100+ hours I spent expanding and revising this definitely doesn’t feel like I’ve made once; I’ve essentially made this book twice. I’m excited to be able to sell it again.

There’s a lot more I can, and will, write about the process. For now, I will say that I’m gonna be embarking on a year of promoting this book. Here’s how you can support the work:

  • Buy the book. Read it and apply it. (That’s why I wrote the book!)
  • Tell one friend about it.
  • I’m also looking to promote this book to larger groups of people—conferences, teams, and companies. If you know someone who might be interested in learning more about how to apply creativity to their marketing, design, software engineering, product, or any other functional team, please let me know in the comments!

My favorite part of this process is how I’d started it; I published it myself, and then I got to work with a publisher on it. That’s how I plan on working moving forward. For too many years, I let gatekeepers, handlers, and the image of traditionally publishing get in my way of me shipping my work. 

If you’ve got a book idea in mind, I’d encourage you to do the same. If you want to write a book, just write it, release it, and promote it. If you can write 1,000 words a day, you’ll be done a short book (the length of my first version) in 15 days. If you’ve already got some drafts ready, you can put it together in 24 hours, or just a few hours like Hassan Osman. Once it’s out, then you approach people who can elevate it creatively to work together and re-release it. (Or, work on your new book!)

If you still feel like you don’t know how to begin, or where to start, just know practically every so-called creative person starts there too. (Note: You’re a creative person if you create something.) I write in Creative Doing, “You might think you need all of that to get started, when in reality all of those resources and insights will come to you as you do the work.”

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