Creating the BIG ENOUGH Sticker
As a kid, I spent time reading skateboarding magazines. At the time, ads often included a line at the bottom that said, essentially, “Send us a dollar and we’ll send you stickers.” I can clearly remember how much I anticipated those stickers in the mail. Stickers have an appeal that goes beyond graphics, paper, and glue.
Today, I’m planning to send people my own sticker and this is the story of how that sticker was designed and how I’m planning to use it.
Why a Create Sticker?
Before my book, Big Enough, hits the shelves, I will encourage people to pre-order it, which means purchasing it before it is officially released. This way, when the book finally arrives, all those sales transactions happen in the same week and the book will hopefully make a bigger splash than it would otherwise. In this scenario, it helps to offer people an incentive for pre-ordering the book. If they (you?) preorder the book and send me the purchase receipt, I will send them stickers, and maybe more, in the mail.
Designing the Sticker
I am not a graphic designer, but I love working with designers and thinking through design projects. Once the idea of designing a sticker arose, I was pumped to work on it. The French bulldog on the cover of the book was my starting point. He’s symbolic of the Big Enough attitude: small and tough. I’ve come to call him “Big-E” and loved the idea of people having a fun, illustrated version of Big-E on their laptop or water bottle.
Instead of using the live-action image, I imagined a stylized cartoon version of Big-E and asked my publisher for the photo from the cover to use as a starting point. Then, I searched for dog illustrations in a style I liked. I found one that was close to what I wanted. It used flat colors and bold shapes that felt cool and modern.
Then I went to Upwork, which is a service I’ve used for years to find freelancers for small projects. I created a new job called “Digital Illustration of a Dog Based on Photo”. I included a description of what I wanted, attached the photo of Big-E and the example photo. I also said the illustration had to include the book website: bigenough.life
Next, I reviewed 15-20 profiles and invited a handful of people from around the world to apply. I’ve had good experiences working with international talent at affordable rates. I connected with a guy named Vadym from Ukraine and hired him. He got started quickly and provided a promising start.
But then, out of nowhere, he said something had come up and that he couldn’t complete the project. Such is life in the freelance market. Disappointed, I went back to finding designers and stumbled upon a profile of a woman named Brooke Braddy who had an affordable hourly rate and illustrations that looked promising. This image from her portfolio gave me confidence that she had worked in the style I wanted:
Brooke agreed to start the next day and estimated it would cost under $100 to complete the project. I was hopeful.
The project turned out to be incredibly satisfying. Over two weeks and about 40 messages back and forth, we tweaked the colors, fonts, padding, size, and more. Brooke was a good listener and had great skills. I enjoy working with people like Brooke who are independent and putting their skills to work from home.
Here are examples of how the sticker evolved over two weeks:
What I appreciated most was the iterative process of making the sticker exactly what I wanted. Every time Brooke sent a comp, another part of the design would grab my attention and kick off more changes. She took my feedback and made it work. For me, that’s how design happens. It’s a process of always asking “what sucks the most now?”
A couple of days ago, I deemed the sticker design complete. Brooke’s initial estimate didn’t anticipate the scale of my feedback, so I gave her a bonus for the extra hours. We were both happy.
A couple of days later, I thought back to those days of getting stickers in the mail and how I loved getting multiple stickers. Sure, I could send pre-order customers three of the same sticker, or I could create a set with different colors. Collect all three!
I went back to Brooke and she quickly whipped up a couple of color options. With just a bit of design time, I now have a set of three stickers for the kind souls who pre-order a copy of Big Enough. Here’s the set:
If you’d like to be notified about the pre-order campaign, you can sign up here.
I write books and run a company called Common Craft. I recently moved from Seattle to a rural island. Here, I write about online business, book publishing, modern home construction, and occasionally, dumb jokes. 
