The Story Behind Initiative’s Cover

July 12, 2019 by Joshua
in Creativity, Education, Visualization

I wanted to share the story behind Initiative‘s cover.

Initiative cover front


The designer first sent a few cover designs. They were contemporary and appropriate for 2019, but they didn’t feel right. I couldn’t point to anything wrong with them, but they didn’t resonate.

When we spoke to review his first designs, I told him that they felt “now,” but I considered my book timeless. It’s not about making apps, blockchain, or the latest fad. I felt ancient Greeks could have used its exercises to find their passions and discover their priorities as well as anyone today.

We started searching for images of classic book covers, especially Plato and Aristotle. I wanted to find the cover of Plato’s Republic from college. Some I liked. Some I didn’t. Then I found this one—actually a title page, not a cover:

It matched what I wanted: simple, timeless, classic, bold.

My name isn’t as known as Aristotle’s and to use only the single name. We felt a single-word title wouldn’t convey its contents enough alone, so we decided to include the subtitle and tagline, but we had our template for the layout. The fonts and colors we could pick from the interior, which he had already laid out.

By the way, Initiative‘s cover background isn’t pink. It’s a picture of old parchment, which includes its texture. You might need to hold the book in your hands to see the subtle gradations, but you should buy the book anyway (from Indiebound | Amazon | B & N | Smashwords).

The image

The spiral staircase comes from concepts in the book. I teach a cycle of knowing your passions, using them to guide taking initiative, which leads to action, which helps you learn your passions, which continues the cycle. Acting on the exercises in the book help you start and continue this initiative-action-passion cycle.

Initiative action passion cycle

Each time around the cycle changes you and develops you so beyond going in circles, each time you go up a level. Going around in circles, up a level each time is like a spiral staircase, so the I use a spiral staircase in the book to illustrate going up levels, leaving behind projects and a life lacking passion to unearth and act on great passions with confidence.


Most people see it as a book on entrepreneurship. For most people it is, though its value is greater, in my experience with most clients and students. Entrepreneurship—forming a for-profit company—is just one application of taking initiative. Some use the exercises to create non-profits. Others organize their communities, friends, or families. Some use the exercises to get hired. Others to get promoted.

But the project is only the short-term result. In the long term, Initiative is about developing you as a person, not just one project. The book’s exercises teach you to become someone who can take initiative any time. It means that you never have to be bored or frustrated with your situation. You can do something about it. It gives you the ability and the responsibility.

My point is that I had to keep the words entrepreneur and entrepreneurship off the cover, even when my publisher insisted, saying it will be in the entrepreneurship section and that’s what sells.

But I couldn’t stop most people from thinking “Silicon Valley engineers in their 20s, venture-backed, high-growth, IPO-bound.” The book helps them, but also the other 90-plus percent of the population.

That’s why the word entrepreneur doesn’t appear on the cover.

Putting it together

Knowing the layout, image, and words, meant only fine-tuning remained.

The rest still took another couple rounds. I shared the samples with friends and family for advice, but mostly refinements were the designer refining details.

I think the cover illustrates the book perfectly. Those who don’t know the meaning of the spiral staircase still mostly see upward movement in it and will find out on reading the book.

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