Instead of hiring just one artist, you put up a contest with a set time limit and a set prize. Let's say you create a contest which runs for two weeks and has a prize of $50. A bunch of different artists will enter to win your contest. They'll all submit their very best effort to win that prize. When the contest is over you have a variety of covers to choose from. If you manage the contest properly, you'll have at least one which is exactly what you are looking for.
How does this work?
It's critical to be as specific as possible when you make your contest. Don't just say "I want a fantasy cover with a jester." Draw a mock-up of what you're after, even if it's rough and unprofessional looking. Describe the cover. If there's a character on it, describe the character.
Here's an example. My friend S. M. Nevermore had a short story she wanted a cover for. She tried twice on Fiverr.com. Both times were absolute failures. So we moved over to Freelancer. I wrote this description for the contest:
We have a specific look in mind for this ebook cover for a short story. Dimensions should be 2813 x 4500 pixels. We have cobbled together the layout but this is quite rough of course. It should be a harlequin jester/joker in a black-and-white outfit. All that should be visible of his face is his smirk and maybe a part of his nose. He should have his arms crossed in front of his chest and in one hand he's holding a playing card with flames on it. The flames catch the eye against the monochrome of the rest of the cover. Note that his outfit is just what we were able to find on the web - it shouldn't be exactly that. It should be a greyscale harlequin outfit, though, so in that same style. We are still finalizing the wording so we'll need the source file to tweak the words and also of course a commercial license since this is for a short story. The demon was summoned by a witch as part of a 'rite of passage' and was supposed to quickly go away but it's decided to stick around and be annoying. So it's childish, annoying, tormenting, and impulsive. It is NOT evil or brooding or deadly. It's more like a sugar-high toddler than a homicidal maniac. Please ask with any questions. Please note on the cover that the demon is off to the left side, not in the center. THE AUTHOR LOVES ANIME/MANGA STYLE ART.
Next up, we included a quite rough sketch of what we were looking for. It showed the jester standing on the left side of the cover with arms crossed, holding a card with flames.
The first two entries came in. Both were a bit rough. We commented on them saying we wanted more of an anime / manga style. Another entry came in which was quite dark. We explained that covers on Amazon need strong contrast in able to be seen at smartphone size.
Each time a new entry came in, we commented on it explaining what we'd like to see tweaked. In some cases the artist would submit a new, better version. But those comments also helped other artists to understand what we were after. The iterative process helped ensure that ALL artists did a better and better job.
By the time we neared the end of the contest we had several amazing covers to choose from. Now it was coming down to fine details! And this is the one we went with, by Sarvy13.
The author was enormously pleased with the results. The cover is exactly what she had hoped for!
So some keys are:
* Go with a reasonable price. You want to encourage talented artists to invest their time even though they won't necessarily win.
* Be detailed in your description. The more clearly you describe what you want, the better the chance of getting it.
* Give the artists enough time to do the drawing or cover creation. Two weeks is a good range.
* Post thank you notes BEFORE the contest ends to everyone who participated. After all, they did the work without payment.
Of course, note that it's possible that you'll reach the end and NOT like any options. This can happen if you offer too little money (say $10) or if you don't describe your ideal cover well. In that case I'd chalk that up to a learning experience and try again, this time adding more detail and more funds.
If you'd like to learn more about S.M. Nevermore, here's her Twitter page!
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