Why My Simple Book Cover Wasn’t Simple
The quest for a stunning, witty book design
The reviews of Apple: The First 50 Years have all been great. But a couple of people on social media have posted about how much they hate the cover.
Here’s one of the more tactful comments:
The cover design was a journey, for sure. I wanted something clean, simple, and iconic, evoking Apple’s design philosophy. But I also wanted a touch of wit, maybe some double meaning. And I wanted something bold enough that it would “read” when it was only the size of a thumbnail icon online.
For example, I love these covers by other authors. Most of them have an arresting, simple graphic—but notice how most of them contain a hidden message or meaning that takes you a minute to interpret. The “1984” quote-mark eyes are especially brilliant:
Ordinarily, of course, the publisher designs the cover. In this case, the publisher’s designs nailed the simplicity, but most of them focused on products of only the last 20 years (iPhone, AirPods, Watch). They didn’t quite capture the historic, 50-year sweep of the book’s contents, and I missed the element of wit or double meaning.
I was obsessed with coming up with something that fulfilled all of my criteria: Arresting, bold, with a hint at a deeper meaning.
I wracked my brains. I even hired some professional cover designers on Fiverr.com (a great freelance-creators website) to suggest concepts. Most of them got the “simple, arresting” part of the assignment, but none of them produced anything with wit or double meaning.
Finally, I went for the nuclear option: I asked ChatGPT for ideas.
And damn—it came up with the coolest cover. It had exactly the emotional power I was going for: Simple, pure, evocative, lovely. It had emotion to it.
You see only part of the logo—and that’s evocative, too. It suggests that the whole thing, if you could see it, would be much too big to fit on the cover. It’s hinting that the story is immense. Which it is!
And if you (over)think about it, this design has a secondary meaning, too: The top contour of the logo is pretty much a graph of Apple’s roller-coaster fortunes over 50 years. It suggests the rise, fall, and rise of Apple—which is the actual story of the book!
(I mean, OK. Realistically, that “hey, it’s a graph!” thing would never occur to any normal person. But I’d know. As a cool party story.)
Everybody loved this cover: My wife, my agent, my editor, random friends. GORGEOUS.
And then—no. The lawyers from both Simon & Schuster and Apple shut that idea down, right quick. Can’t use the Apple logo, not even part of it. No book about Apple has ever gotten away with using the actual Apple logo, at least not in the last 20 years. They always fudge it:
Well, crud. I was back to square one.
Finally, in the twilight of sleep one morning, I started thinking of the geometric primitives that always captivated Apple’s design superstar Jony Ive. Squares. Triangles. Circles. OMG, the circles!
Circles are all over Apple’s 50-year history. There’s the corporate headquarters, Apple Park—a one-mile ring. Its round Steve Jobs theater. There was the first iMac mouse (blecch). The “sunflower” iMac. And its speakers, and its iSight webcam. The iPhone’s Home button, its camera lenses, its MagSafe charger.
Above all, there was the iPod clickwheel: the iconic feature of the iconic product that turned Apple from a computer company into an electronics company. That wheel is the instantly recognizable face of the product that launched the company we know today. It was a brilliant representation of what makes Apple Apple: Simple, intuitive, powerful, beautiful—all at once.
What if the cover graphic represented the iPod clickwheel?
And as the cherry on top, that click wheel contained that wit, that hidden meaning I’d been looking for! Not the rings—the << and >> buttons!
What’s the meaning of those buttons, away? They suggest a timeline! They mean “look backward” and “scan ahead”—which, of course, is the entire purpose of this book!
I whipped up a mockup in Illustrator.
The publisher’s designers tweaked the design and debossed the ring (stamped it out of the paper, so it’s raised to the touch). And they turned the << and >> buttons solid black instead of gray, to emphasize their timeline-ness:
So there you have it: The story behind the cover design for Apple: The First 50 Years—mostly admired, occasionally despised. Somewhere out there is an idea that’s even cooler and wittier and more symbolic. But so far, I haven’t found it.
As for my correspondent on X.com: I explained my thinking on the design, just as I’ve done here. This time, his reaction was much better.
(P.S.—Hey New Yorkers—come say hello! On Tuesday, March 24, I’ll be joined onstage by the Wall Street Journals’s Joanna Stern and WIRED’s Lauren Goode at the historic Cooper Union. There will be thoughts on Apple at 50, stories, humor, PTSD—and some Pogue song parodies at the piano. It’s free. Register here.)
UPDATE
After all that, the publisher has let me know that they’re going to have to CHANGE the design of the final book cover. They’re going to add a new line of text, based on the New York Times bestseller list.
In this case, I’ll allow it.












Sorry. I’m calling BS. I think the cover is fantastic
Your cover was great from the get go. One popular author who sold a million books got 90% positive reviews and 10% negative reviews. He said he writes for the 900,000 who will buy his next book.