I’ve wanted to share a story for a while about the crazy process behind my book cover design. I am a diehard do-it-yourselfer in most cases, but since I have absolutely no artistic talent, I knew all along that I would need outside help for my cover design.
 
I read somewhere that the going rate was about $750 for a good designer who might come up with a half-dozen or so alternative concepts. But then I read about a site called 99designs.com. They run contests for book covers (as well as logo designs, website designs, album designs ... just about everything). You start the process by sending a “cover brief,” in which you provide basic guidance, and examples of other covers that you like. Even more important, you must also offer a financial prize. At least in theory, the higher the prize you offer, the more designers – and the better designers – will participate in your contest. Based on the guidance provided on the 99designs website, I offered a prize of $649.
 
The “cover brief” that I uploaded included the picture below, taken by my wife Barbara of Chartwell, Winston Churchill’s country home. I also provided a disclaimer that designers should not feel compelled to use this picture. I was more than a little nervous, not sure if any designers would participate.

I was spending a lot of time with my dad at the time. It just so happened that his clothes dryer was broken, and its replacement had not yet arrived. After doing a load of wash, I threw his damp clothes into a bag, clicked “Start” on the 99designs site to begin the contest, and drove to a laundromat two blocks away. The first two designs hit my inbox while I was waiting for my father’s clothes to dry. After 5 days (the length of most contests), I ended up with 145 designs from 35 designers. Some were great, some were horrible.

I was supposed to then narrow my selection down to 6 designers for a final 3-day design cycle. I was so emotionally drained by this process, that I picked just 4 finalists to work with. The entire process was done online, and I had the ability to request specific tweaks from any of the designers. In the end, it was truly painful to reject the 3 “losers.” The winning designer was incredible to work with, and graciously made a few minor changes even after the contest officially ended. I know his name – Fayyaz Ahmed, aka dezinir.99 - and that he lives in a time zone that’s 8 hours different from mine, but that’s about it. I highly recommend Fayyaz and 99designs.com.
 
This will give you an idea of the range of designs I got to pick from:

My one “contribution” was to ask Fayyaz to change the font on the cover to Courier … to tie it to the typewriter on the cover. As usual, I probably overthought this.

The author Ryan Holiday has been a big inspiration from the earliest days of my project. His book Perennial Seller, and a newsletter of his titled “22 Rules for Creating Work That Stands the Test of Time"are still among the most reliable sources of inspiration for my writing and marketing. Of all the things I’ve read from Ryan, my absolute favorite is this quote from his newsletter:

"That saying “You can’t judge a book by its cover”? It’s total nonsense. Of course you can judge a book by its cover—that’s why books have covers. They’re designed to catch people’s attention and draw them toward the work - and away from all the other works that stand equal on the shelf."

Thanks for reading (and for looking at these covers),
Bill
 
PS: One other thing I’ve learned during this process is that there are two kinds of people in the world: those who recognize Chartwell on the cover of my book and - in the majority - those who don’t recognize Chartwell or care that it's on the cover of my book ;-} I still really like my cover, though!