My “Mad Men” Moment
By: Theodore Deden
Tags: Advertising, Python, Authors, Marketing, Books

I had a challenging task ahead of me. The book I had been working on for months would soon be ready to publish, and I needed to organize some cover art. I myself am an amateur photographer, and I am pretty decent at producing PowerPoint slides for business purposes, but this is the extent of my graphic design abilities, and this wouldn’t be sufficient for my book, not by a long shot. In fact, it wasn’t just design that I needed — it was inspiration.

It easy to sell quality vegetables at a vegetable market because people know they need them and the market is where they expect to find them. In contrast, my book on Business Python is neither a typical business book nor a typical programming book. It is an innovative hybrid that is designed to present (Python) programming to a new (business-oriented) audience. The challenge that the cover design needed to address is that no one is looking for such a book, and no one expects to find it, either among business books or technical ones.

This is actually one of the tougher marketing problems to solve, because before you begin to tell a potential customer about how white your toothpaste will make his teeth, you first have to convince him that he needs to brush his teeth to begin with. After all, it has only been in recent times that dental hygiene has become widespread. During prior periods of history, although dental problems were common, it hadn’t occurred to people to look for a preventive treatment.

I think we will look back in a few decades on how we used computers in much the same way as we currently look back on the dental hygiene of cave men. If simple, cheap, effective solutions are available to make our lives better, why aren’t we using them? Why aren’t we brushing our teeth? Why are we still rubbing sticks together to make fire, when there’s a butane lighter in each of our pockets?

Maybe, having read the previous few paragraphs, you are getting curious about what I wrote in my book — if for no other reason than a sense of intrigue. But notably, you had to spend a couple minutes’ reading to get to this point. My book cover challenge was to come up with a front cover design so visually interesting that one is simply compelled to turn over the book and read the back cover (or read the Amazon description, as the case may be).

A template design just wouldn’t do. What I needed was the input of an inspired professional. For this, I turned to a popular freelancer site where thousands of talented graphic designers (among others) look for work from all around the world. I started out intending to hire one to do my cover, but as I was signing up, the site offered to set up a contest for the design, thus allowing me to benefit from the best insights among many designers, rather than having to pick just one.

I decided to set the contest’s duration at ten days. I figured that this would be long enough to allow people to be inspired, but short enough to keep things in perspective. I set the contest award at $200, which I paid to the site up front, along with some fees to promote the contest among freelancers. According to the platform, based on past experience with similar contests, I could expect to get over 100 entries. (It actually turned out to be over 330.)

When I set up the contest, I massively underestimated the complexity of the task. I provided a modest set of requirements describing the book, the intended audience, and my goals for the project. I summarized it for the contest participants as follows:

Overall, I am looking for something creative that catches the eye and begs the reader to open it up. If the book is on a co-worker’s desk, it needs to draw the attention of everyone walking by. It should give the impression of a tool that is designed to empower an average person — to make the weak strong and the strong invincible.

I also provided a little background on the origin of the Python name, perhaps as an inspiration for design:

Be aware that Python was named after Monty Python, and in this vein I would love to see a bit of playfulness and graphical humor mixed in if possible — but again, staying away from anything that could infringe on others’ intellectual property.

After only an hour or two, I had already received the first entries. As I looked them over, I knew that I had not provided enough guidance. The entries either weren’t interesting enough, weren’t relevant to the topic, or were so generic that they could have applied to just about anything. At least three contestants submitted designs with skulls for some reason, of which at least two also had flames drawn on them or around them. Skulls with flames! Just, no.

More than a few designs were modern, clean and appealing, but offered no hints whatsoever as to the content of the book. One such design (submitted by this contestant) looked like this, the “torn-paper look” being very popular among early entries:

Modern, clean, and entirely generic

This contestant apparently thought that bright colors might elicit some interest in the book:

Author? LSD dealer? Why choose?

This guy took the opposite approach — no hint as to the content of the book, but artsy and plain instead of psychedelic:

Business Python: for squares with simple ideas… maybe not?

The best of the bunch was beautiful and professional-looking (by this contestant), but again entirely generic. It said, here is a professionally-produced book but it didn’t say, pick me up and check me out.

Best of the early entries: beautiful and professional but entirely generic

The Aha! moment came when I realized that what I was really engaged in was advertising — or in a broader sense, marketing. As an author, I had always implicitly seen cover art as I imagine that a chef sees a garnish on a plate: designed to stimulate the senses and convey professionalism but not an integral part of the meal. But there is a critical difference: by the time the restaurant guest sees the garnish on the plate, he has already committed to paying for the meal.

With a book, the cover is the first thing that people see and for many books, the last thing they see. No one seems to heed the old advice, to “not judge a book by its cover.” In fact, that advice seems pretty dumb when you think about it. How are you going to choose how to spend your reading time, if not by looking at the cover? First you look at the front cover to check if the topic may be interesting and relevant to you, then the back to confirm and motivate the decision to read it.

When designing that cover content, I was coming to realize that I needed to give people a reason to want to pick up this book, turn it over and read the back cover. The back cover text itself focuses not on the what of the book, but rather (with a nod to Simon Sinek) on the why. On what the book will do for you. On the difference between this and the typical business and computer books out there, and on the true-life testimony of empowerment in real business contexts.

I was happy with the back cover content, no matter what the design. But I knew that no one would consider reading that text unless the front cover could be made compelling enough.

If I had chosen to go the route of a traditional publisher, that publisher would have experts in graphic design and book marketing who could help me come up with the best cover possible. But (for a variety of reasons) I chose to self-publish, so my first stop was to search for input from firms that specialize in supporting independent authors like me. I found two serious organizations in this area, and both encouraged me to choose a long, descriptive title and subtitle. That way, the words on the cover would be sufficient in themselves to whet the potential reader’s appetite.

I considered this, but pretty quickly dismissed it. For me, this would have meant a title like Python Programming for (non-technical) Business People: How To Harness the Power That Turned Me Into an Office Hero. Maybe those guys were right and this kind of title might have been more effective at selling the book, but this just didn’t feel right to me. I felt that it cheapened the book, and I wanted the selection of title and subtitle to confirm the quality of the content that I had produced.

Next, I turned to David Ogilvy — or rather, to his book, Ogilvy on Advertising. For those who don’t know of Ogilvy, he was a marketing genius, a real life “Mad Man” known to anyone who has ever indulged so much as a passing interest in marketing. His own book cover already hints at the man’s individualism and general approach to the task:

As the book dates from 1983, it focuses on printed forms of advertisements, though the principles are universal and timeless. I re-opened the book, looking for ways to elicit emotion in the front cover that would compel a casual glancer to turn over the book and read the back cover, or even open it and read the introduction. Finding several, I returned to my contest site to provide additional guidance to the contestants:

I’m posting here some extended comments on what I’m looking for. Even if you are unsure whether to submit additional entries, I would encourage you to read through these comments… if you learn this well, you can set yourself apart from other graphic designers when doing book covers, flyers, printed ads, etc. What is the goal of this exercise? The goal is for me sell my book, right? And that is difficult because my target audience doesn’t even know that they need Python. With this book, I’m seeking to market an existing “Product” to a new segment of the population that would never on their own think to use this product. The title Business Python points in this direction because it is usually not business people who need Python — it is usually IT people, or data science professionals. Why should a business person bother with this? — I answer this in my book, but the answer requires more space than a well-written title or subtitle will allow. The back cover of the book is going to contain the proverbial “elevator speech” — the short form answer that will either hook them, or not, depending on the words I write. The front cover needs to compel them to look at the back cover. That’s why it’s not enough to have a work of art, or something hinting at some kind of amorphous “business success.” These aren’t compelling. There are a gazillion self-help books out there, a gazillion Business/success books, and a gazillion Python books. I need a potential reader to react to the cover in a way that they wouldn’t react to any of those others. Good advertising (and the cover is an advertisement, after all) always taps into emotion, not analytics. So how does this work in practice? There is a part of the human experience that is universal. Love, loss, grief, hope, ambition, lust, joy, tenderness, surprise, humor, disappointment, fear, etc.. Good advertising taps into these. I have a book Ogilvy on Advertising in my hand with some great examples from the past. Page 119: a sad-looking boy of about 7 or 8 clutches a broken baseball, and on the other side of the page, a short article on “how to get your money back at Sears”. Emotional.

The next page has a beautiful woman wearing a fur coat and smiling broadly, looking at the camera with a look that just says “THANK YOU I LOVE IT” and a short article on “How to buy mink at Sears for Christmas.”

Think of the Marlboro man — a rough, tough cowboy whose image conjures up (or did for its original audience) fond memories of watching heroes and villains duke it out in classic Western films, or memories of spending time in the open air. Or, how about this Dove soap ad from page 72 of Ogilvy: a woman is talking on the phone while taking a bubble bath, a blissful look on her face, and the copy: “Darling, I’m having the most extraordinary experience… I’m head over heals in DOVE!”

Or page 73, where an old ad for a VW Beetle just has a picture of the car and the word “Lemon” (a word for an absolutely worthless car) — then in small text explains the stringent quality control processes that the cars undergo at the factory and why this near-perfect car was held back.

No one would read about quality control if that were all there were. It is the surprise at having a negative word being used there that compels the casual glancer that he must read on. In the same vein, page 71 has a picture of a can of soup being poured into a drinking glass with ice (a new use for an old product, sound familiar?) and text to explain what additional condiments can be added to make a delicious summer drink.

None of the above examples are 1:1 applicable here for my book cover, but should give you an idea of what I am looking for, and what I mean by evoking emotion and compelling the casual glancer to read further, and I hope this will comfort those of you who have submitted excellent designs which I have rejected (or will reject) for lack of emotion. Forget the quantity / variations-on-a-theme approach. What this contest is about is that factor that compels the glancer to read more, even if he has no interest in Python whatsoever. Give me the best design that does that, and you will have won the contest.

One might think that after feedback like this, the contestants would have spent some time just thinking about the task at hand — especially considering that there was still more than a week remaining in the contest — instead of churning out more and more inadequate, unemotional cover designs. Unfortunately, for a very vocal minority, this just wasn’t true. Huge quantities of designs continued to roll in, with some combination of light bulbs, business charts with arrows pointing up (and in one very odd case, with an arrow pointing down), brains, futuristic neural-network type things, mechanical gears, and various business-themed clipart-type graphics. Time after time, I would give the same feedback on the entries: generic, unemotional, please see my prior comments.

Clipart jamboree by this contestant

I wonder if this contestant was a Malcolm Gladwell fan…

I can see where the artist was going here, but I find it just… creepy.

Nice and light, but the artist is unable to differentiate this from the gazillions of other business books out there

I loved the Star-Trek-style font and Stranger-Things-esque “dark reflection” but this artist, too, failed to elicit the emotional response I was looking for.

One of many designs from the lightbulb-brain-department (artist page)

Lightbulb-brain plus headphones? Really Mr. K?

Even after providing my additional input and references to Ogilvy’s marketing brilliance, I still continued to receive one variation after another on the above themes. Light bulbs, brains, mechanical gears, office-themed clipart, and arrows of various kinds made up the bulk of the submissions I received, despite the hours I spent on the site providing kind but firm feedback that these were not the droids I was looking for.

Refreshingly, there were some wonderful exceptions to the above. One contestant gave it some serious thought and came up with this, which she delivered, together with an explanation of what all the symbols mean:

A gallant effort but generic and undifferentiated

Unfortunately, the entry is rather one-dimensional. Every business book promises to carry you to the clouds, improve your time management, bring career results and make you happy, so there is no reason for anyone to pick up this one in particular. I also wasn’t happy with the hot air balloon as a symbol, as it seems directionless to me. Python is anything but.

Some other designers leaned toward intrigue as a way to capture people’s interest. For example, one contestant submitted this entry:

Definitely has some appeal, but I’m not ready to compete with Stephen King

Although I really liked this design, it just wasn’t suited to a nonfiction work like mine, especially since the open door didn’t tie in naturally to any of my content. It was simply off point.

Coming closer was this guy’s entry, which still lacked that the emotionally compelling aspect I was looking for, but at least was visually relevant and pleasing to look at (and it was far more appropriate for a nonfiction book):

Business hacker?

Another guy took a similar approach, also with a dark color scheme — I find it very appealing graphically, but I have no idea what the image is supposed to be showing. Instead of being alluring, it comes across (at least to me) as just confusing:

If you can’t beat ’em, do your best to confuse the hell out of ‘em

Then there was this one, which to me looks like a movie poster for a cheap psychological thriller. The artist shows an enormous creativity here, but I find it just bizarre that she would submit this as a cover for a book on Business Python:

Bizarre entry for a book on either Business or Programming topics, let alone both

To be perfectly fair, that wasn’t her only entry. She also submitted this one below that I found strangely compelling, except that it just didn’t have anything to do with the subject — and besides that, it wasn’t eliciting any emotion from me.

A great cover for a scifi or fantasy novel, but not a nonfiction book on computer programming.

From the this-book-will-either-enlighten-you-or-steal-your-soul department (and this user) came this submission — nice graphic work with only a tentative link to anything remotely resembling Business Python:

Python: Frenemy for life?

A bit more promising was this entry by a contestant who explored the human/machine interface at the heart of Business Python:

The right direction: the human/machine interface

This was definitely the right direction, but I had three issues with it. First, the human face in the back was too impersonal, lacking in emotion. Second, the whole thing was still a bit generic. And lastly, the android-like figure looked too much like this guy:

Luckily, there were others (like this woman) who were submitting entries that explored the man/machine interface theme, as exemplified below.

FACE OFF: One of my favorite entries for its topical and evocative central image

That was one of my favorite entries because of the central image used. The human faces reflecting machine logic perfectly capture the topic addressed by the book, and the fact that they are facing one another brings an element of emotion into the image. This screams to the casual audience that there is a story here, a story worth reading. It’s not a perfect entry — in particular I would have insisted on getting rid of the white box around the word “Python,” for example — but it was one of the better ones I received.

Another great entry was provided by a talented graphic artist who was able to combine the man/machine theme while maintaining a deep level of emotion to create a highly compelling entry:

CLOCK MAN: Brilliant work, on point, emotional, and beautiful

Then there was this one, exemplifying perfectly the cooperation between man and machine:

CABLE HAND: Perfect central image — human and machine hand-in-hand

My personal favorite, however, was submitted by a brilliant Argentinean designer who built on the heritage of the Python name to come up with a clean, beautiful cover design with instant recognition among fans of Monty Python’s Life of Brian:

LIFE OF BUSINESS PYTHON: My personal favorite

The back cover was also perfectly aligned to the theme:

Absolutely brilliant work

A similarly insightful American designer took her time in coming up with a design reminiscent of Monty Python’s Flying Circus (with an additional nod to Monty Python and the Holy Grail). It was the Flying Circus that was the original inspiration behind Guido van Rossum’s choice of name for the programming language, so in a sense this is the most historically accurate, but in spite of this, for me it just didn’t hold as much emotional cache as the Life of Brian cover:

FLYING CIRCUS COVER: Inspired, solid work, just not as emotional for me as the Life of Brian variant

The remainder of the 330+ entries I received over those ten days either bore some combination of the aforementioned problems, or else featured known copyright issues. In some cases, both were true. In any case, with the clock now completely run down on the contest, I now had to choose a winner and commit to a cover for my book.

As mentioned, my personal favorite was the Life of Brian cover, but before I committed to that one, I wanted to get some feedback from other people who weren’t so close to the project. Over the course of two weeks, I approached friends, colleagues, and family members to ask for feedback. I showed them the designs above and asked them which one stood out the most, which was most emotional, most intriguing, and which would be most likely to motivate them to pick up the book and look into it further.

Out of these feedback discussions, a clear winner emerged, and it wasn’t the one I had anticipated. Instead, it was the CABLE HAND cover. This elegant design did an excellent job, I also had to admit, of capturing the theme of human-machine interaction in a deeply emotional way, one that not only reflected the topic of the book but did so in a compelling and visually appealing way. While other designs did receive some positive feedback, I had to choose just one — and this was going to be it.

Also based on the feedback I received, I took the opportunity to rethink the title and subtitle of the book, eventually opting to keep Business Python as the title but modifying the subtitle to be an example-based guide. In this way, I could capitalize on the guide aspect of the hand-in-hand imagery, while emphasizing the stark difference in approach between typical programming books based on theory and my own, based on examples. The final, edited cover looked like this:

Final front cover: beautiful imagery emphasizing man-machine interaction and the guide theme

This should be the end of the story, but it is not. Having chosen a winner and worked with the designer to make the final adjustments to the subtitle and rear cover text, I then moved on to concentrate on many other aspects of book publishing, content that the cover work was done. I was wrong.

As I prepared to go to print, a friend who reviewed my content sent me a message, writing, “You might have some copyright issues with your book cover down the road… I found this.” Clicking on her link, I found the same central image of the human hand and the cable hand, prominently displayed as part of a Capgemini advertisement. Crap.

This was very bad news. Two weeks from my book’s release, and I discover that the designer who created my book cover had stolen the central design element from someone else and passed it off as his own. And it wasn’t just the book cover anymore. The website, the book’s video trailer — all used the same design that would have to be changed if I couldn’t get permission to use the image. Not only that, I would need something to change to. That meant that I would have to approach one of the runners up to see if they still had their entry and what price they would sell it to me for. I was prepared to delay the launch if needed — though I hoped it wouldn’t come to that — while modifying the cover and ordering proofs, and so on.

Working quickly, I tracked down the copyright owner for the CABLE HAND image and worked out a licensing deal. The licensing fee hurt, but not as much as it would have hurt to redo the whole cover. Especially since, in the end, I felt that the chosen cover design met all my goals. It features a compelling emotional image linking back to the topic in an elegant way. I call that a win.

I learned a lot of lessons over the Fall of 2020 as I selected a design for my book cover and prepared to go to print. One big lesson is to be more careful when dealing with freelancer designers and to check better for possible plagiarism. If it looks too good to be true, it probably is.

Most importantly, however, I came to see book cover design as an important aspect of marketing a book. People rightly use the cover of a book to discern whether that book deserves further attention. Good cover art, therefore, like good advertising, will tap into emotion to pique a reader’s interest and get her to open the book and read more — and this is all the more important when the book is written to an audience that is not expecting it.

If you are interested in learning more about Business Python: an example-based guide, see the companion website: https://business-python.com