5 Titles, 50 covers, and 179 days later: How Unhinged Habits Came to Be

The original title of the book was Too Early for Coffee.

It then became The Obvious Challenge, The Obvious Changes, 8:4 Habits, and eventually Unhinged Habits.

Here’s the 179 day journey that led to the title and cover. I dug up some early designs and emails to my publisher to show you too.

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Too Early was what the book was sold as. The publisher never liked it.

We first started working on the cover on January 9, 2025 under the title The Obvious Challenge.

I liked The Obvious Challenge because of its pairing with my previous book, The Obvious Choice. My thinking was that books are so hard to sell and pairing these two together as a series would benefit both.

Here were the first designs:

The designs don’t work because the title doesn’t work. The title of Choice isn’t effective. And the book’s reach has suffered as a result.

And yet, for some reason, I thought it was a good idea to repeat the same mistake of opaque messaging.

We struggled through 8 series of designs with the original title. Over 40 variations. None worked. Everybody was getting frustrated. By then, the title was The Obvious Changes.

On May 16th, 127 days after the first cover was presented, I asked if I could change the title.

Here’s the email:

Figuring out what a book is really about is hard. Distilling its essence into a single sentence is the hardest part of the process for me.

Everything became clear the moment I realized that this was a habits book. In retrospect, it was obvious.

Not only that, a fabulous way to sell books is to position it as a new take on an existing market that’s proven to sell books.

Habits. It’s a habits book.

The next question: What kind of habits?

By June 23, over 50 cover concepts and 126 days later, we were well past the deadline and more or less agreed on 8:4 Habits and had a cover we were going to go to print with.

Here’s some concepts:

The 8 : 4 was taken from a central concept of the book. My lifestyle of 8 months in Toronto, and 4 months abroad––not encouraging people to travel. Instead, extolling the virtues of returning to a more seasonal way of living.

But, as you can see, it still wasn’t quite right.

8:4 took too much explaining. And seasonality, while a key idea in the book, is not the theme. The theme is that intensity is what’s needed for transformational change with any aspect of our life’s triad (money, health, relationships) and that maybe, just maybe, consistency, while undoubtedly valuable, isn’t enough.

But also, a book title’s gotta hook. It’s gotta grab you by the balls. Meet you where you’re at. Make you stop. Make you want to know more. Make you feel like you need to know more. If you have to explain a book title, it is not a good book title.

Did you notice the subtitle in the pic above?

An Unbalanced, Ambition, and Almost Unhinged Approach to Living in Intentional Life.

Despite being a habits book, I was positioning it as a book about lifestyle design. Of course it’s about that. But lifestyle design isn’t a good book buying market. Habits is. We needed to keep the book positioned for habits.

But that word.

That word.

Unhinged.

I don’t know why I love that word so much.

It’s not supposed to be a positive trait. But it feels positive.

Unhinged.

. . . That word has a weird kind of appeal.

And the book really does deliver on the premise of fighting back against normality, unfulfilling routine, and consistent mediocrity.

I posted the covers for 8:4 Habits in a group of authors I’m in to get feedback. Mitchell Baldridge, CPA, CFP® left the comment that transformed the book’s trajectory:

The response from the rest of the group was immediate:

By this point, we’re far past every imaginable deadline. The book was even already up for preorder with the old title and cover.

But I knew Unhinged Habits was the right title in my gut.

And so, I wrote another email to my publisher and nervously waited for their reply:

I was nervous to send the email. Thankfully, I didn’t have to wait long for a response:

After that, things moved along quickly.

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The lesson I learned about design is that if the cover and positioning of the book isn’t nailed down, it’s straight up impossible to decide upon a cover.

And it helps to have a group of colleagues give you honest feedback.

On July 7th, 179 days after the initial cover was proposed, 5 titles and over 50 concepts later, we had the cover.

And I think we nailed it.

-Jon

P.S. I’m surprised that more people don’t know that when you preorder a book, you are guaranteed the lowest-ever price.

If you preorder Unhinged Habits today, if Amazon ever discounts the book between now and the release date, you get refunded the difference.

This is why I always preorder books.

Please consider preordering Unhinged Habits in whatever format you prefer (hardcover, audio, or kindle) here.

P.P.S. Thanks to David Epstein for asking me about the cover and prompting me to dig up all this stuff and share it.