I’ve recently shifted my focus on some commitments and freed up more energy for my own projects. Which essentially means I began staring down a lot of ideas with my best “Ok—let’s go!” attitude. And nothing happened. And I grew disappointed, because despite all my zen-like intentions, I am still wired for productivity at the end of the day. If I didn’t have a few new poems or a new business strategy or a new something at the end of the day, what was I doing?

Carl finally concluded: “You haven’t been shitty at anything in awhile.”

I was surprised to realize how true that is. I’m the last person to want to be an expert. The idea of an “expert,” for me, suggests a level of mastery and experience and assuredness that I just don’t think exists these days. Expert is a point-in-time achievement… as long as the world continues to change (and it does), you should change with it. Better to be a perpetual student. 

But I started to see how pervasive expertise can be. Much of our lives, especially as entrepreneurial types, is spent tuning our strengths and adapting ourselves (and our companies) to create or connect to opportunities. At a certain point, you’ve seen enough scenarios to work from a set of patterns… if x happens, then we can do y. If x-type customer crosses our path again, then we will offer y sooner. In some ways, this is as it should be. This is natural evolution and efficiency that comes from learning and being self-aware.

But in other ways, this process can create a comfort zone that throttles creative thinking. You grow more strategic but not necessarily more creative. Ideas and energy are filtered through the scenarios. Creative instinct gets doused in so-called “experience.” Or in my situation, the ideas and energy are expected to produce something, or produce outputs of a caliber similar to previous ones, within the same amount of energy and efficiency. And when they don’t? Creative paralysis.

In short, we forget how to be shitty. 

Shitty looks a lot more like flailing than it does, say, brainstorming. (Isn’t it funny that even brainstorming sounds so logical and productive these days?) Shitty is your brain’s Fight Club. It’s where your idealism beats up your realism and vice versa. It’s messy, and you feel like you haven’t trained well enough to land a punch, and you are ashamed that you have to fight so much at all… because shouldn’t you know more than this? At least enough to skip the awkward phase, where your ideas must learn how to walk?

And I guess that’s the point: No, you shouldn’t know enough. Because if you did, you would only envision what works, and you’d stop imagining what’s possible.

So I’ve been trying to be open to that. Giving myself permission is the most important part.

In terms of tangible practices, one thing I’ve started to do is write down my questions, not just my ideas. What we wonder about is a path to what we might imagine or create. These can be bizarre questions (e.g., does anything naturally occurring travel only in a straight line?), but when you’re someone like me who likes to make lots of things in lots of ways, there are many ways they might get answered — through a poem, through an app, through a new service, etc. 

What do you do to get comfy with the shitty phase of creativity?

Carl and I are in the midst of what we’ve decided to call Version One Weekend. It’s similar to Startup Weekend and other events, except it’s just the two of us, involves more inside jokes, and we can crash in our own bed at the end of the day. Basically a nerd’s idea of a dream date. Here’s how it works:

1. Have breakfast at a yummy place, preferably one where they make you feel at home. You want to be able to take your time and not feel embarrassed when you invite the sixth helping of coffee.
2. Review old project ideas in your Evernote or trusty Moleskine. Brainstorm new ideas as needed. Focus less on qualifying ideas at this point and more on just putting four to eight possibilities on the table.
3. Before leaving the restaurant, select an idea that you can make happen, even in a simple form (i.e., “Version One”), over the course of the weekend. This is where Carl and I struggle. I have a penchant for systemic thinking, and Carl loves to solve a complicated problem. Many of our app/project/company ideas have layers that depend upon each other to get to a successful first draft. Which means more upfront development time and more potential points of failure. Today, we booted any ideas that could turn into “systems” and instead considered apps with a singular purpose. (Bonus points for ideas that are fun.)
4. Forgive yourself early and often. The idea has probably already been done in some form, because most ideas have been. We never said our goal for this weekend was to create something incredibly original.  We did search around to see just how saturated the idea or similar concepts might be, and we felt like we’d be contributing something different enough. But most importantly, we just want to build something. Because creating is the best way to keep learning. 
5. Break down your would-be creation (a.k.a., manage your expectations). Identify the simplest but most essential parts – the pieces that comprise the core idea or experience. These pieces are “Version One,” and they are all you should expect to create during the weekend. We broke our idea into three main pieces of functionality, and we are only focusing on the first piece this weekend.
6. Build accordingly. Reconnect and refocus as needed. 
7. Venture capital. (Just kidding.)

So, Carl is in the midst of building out our Version One, and I’m developing a name, initial messaging, and rough pricing ideas (if we get far enough for that). I’m excited to see where we land by the end of the weekend… at the very least, we’ll be a couple steps away from just talking about our ideas, and that’s a heck of a lot closer to where I’d like to be headed.