As with all new ventures in my life, I viewed publishing my first book with a constant internal pessimism. This meant that for 10 months, I was fully expecting something to occur which would derail the process and kill the book. 10 months. Constant.

Now, I’m an optimistic guy. Try it. Walk into my office during a dire, screwed situation and you’ll see a grin on my face. I thrive in chaos and despair not because I love being screwed, I thrive on it because I’ve often been there before. When someone runs into my office yelling about how a VP is going to eat us for lunch at a meeting later in the day, I optimistically respond, “Relax. We taste horrible.”

So, why so internally pessimistic?

For me, a healthy dose of pessimism drives all new ventures. They require pessimism because I don’t know what I’m doing which means, yeah, I’m going to screw up. Pessimism — a belief that things are not only bad, but also tend to get worse — is the perfect mindset for staring at the unknown. It prepares you for disasters because is imparts the belief they are going to occur.

There are less comfortable definitions for pessimism, such as a belief that evil is going to win over good, but I’m not talking about that pessimism. I’m not talking about the passive pessimism employed by those morosely staring at the world thinking, “Well, at some point, I’m fucked.” I’m talking about pessimism where you are actively engaged in worse case scenario analysis. I’m not talking about pessimism based on fear (which is paranoia, by the way). I’m talking about constructive negativity.

Right. So, the book. 10 months of constant pessimism. This is why when the first batch of covers for the book showed up, I thought, “Ok, good. I knew they’d be awful.”

Worst Case Scenario

Here. Play along at home.

Not complete disasters, but clearly cliché. I mean, c’mom — cheese? Didn’t we move our cheese around back in 1998?

There were two reactions I could have had when these initial comps showed up. The first was getting lost in despair. Anyone who has ever been in a bookstore knows that you’re not browsing books; you’re browsing covers. To have a chance in a sea of covers, you’ve got to have a compelling visual that grabs people. These initial covers said nothing to me, and if I hadn’t known these meaningless covers were coming and that they’d be bad, I would’ve spent a couple of useless weeks mired in stunned silence. “Well, maybe the writing will carry the book…?”

Since I signed the contract, I’d pessimistically prepared myself for the fact that I had no idea how much work I was signing up for, I’d end up hating some of my favorite chapters via the editing process, and that the initial covers would suck. I knew they’d suck because I knew the cover had to be great. Knowing that nothing is great in its first iteration meant I didn’t think twice about moving on and calling in reinforcements.

I first sent the covers to trusted friends, and the reaction was swift and unanimous: “They suck and they don’t look like Rands.” Another friend provided a list of talented illustrators. Amongst that list was a gentleman named Kevin Cornell. A brief IM introduction later, Kevin and I were chewing on cover ideas, leaving pessimism for productivity. The elapsed time from sending out crappy covers to trusted friends to Kevin and I chewing on new concepts for the cover was a day. (Sidebar: my only complaint about working with Kevin is that I’ve yet to figure out another project where I can work with him again. Hire him.)

Kevin generated all of the illustrations on the cover, as well as the sidebar art you see cycling through the weblog, from my horrible sketches and his artistic impressions of chapter titles. My fine publisher, Apress, took these initial concepts and generated the final cover, which incorporated the handwritten, humorous, and relaxed design that hopefully compels people to pick up the book from the shelf at their local book store. I love it. When they sent the first draft that incorporated Kevin’s artwork, my reaction was instant: “It’s perfect. Don’t touch a thing.”

Productive Pessimism

Pessimism is a lot of work. Expecting the sky to fall at any moment means you spend a lot of time constructing sky-falling escape strategies that you may not need. The goal with all this pessimism is to transform these strategies into experience. Your job is to survive and you do that first by successfully traversing new projects and then learning from both how you screwed up and, hopefully, how you succeeded.

Conversely, you need to remember that new projects, great ideas, and outlandish proposals never ever start with pessimism. They start with optimism. They start with, “Of course I can do that.”