Iteration for Creative Leverage

When someone asks you to “create”, the assumption is typically that you will first brainstorm, then implement one of the ideas brainstormed.

This works when the task is small. But what if you have something potentially very big and you don’t have all the answers, or are even able to estimate the scope or find a starting point? This is where a lot of folks, including myself, have gotten stuck. It’s not possible to hold the whole thing in your head, or to “brainstorm harder”. And it’s scary and demoralizing to face a big problem like that and be lost.

Here is how I have solved this problem, across every medium I’ve worked with. I hope it will help you.

The first step I take is to roll dice, by finding a point to iterate on. I can gain control over the risks of the things in the brainstorm by breaking them out and developing them in a more limited mode. This might take the form of a document, or a prototype, or some other artifact. Changing mediums helps if the other medium is faster to work with. The point is that several iterations will take place of this artifact, rather than trying to develop the entire work in a single medium and iteration without breaking out any part of it. Parts of the artifact might appear in the whole work as-is, but that is not assumed.

What is most important to recognize is that iteration processes can recur at multiple levels, and the process is mostly limited by your awareness and ability to switch between details and big-picture. If I’m stuck on a drawing, I can relax from final quality temporarily to explore with sketches and references. If I’m stuck writing a song, I can concentrate on a few elements and iterate through those in a few variations while ignoring the song as a whole. And so on.

Iteration is guided by asking questions and following through on them: “What if I try this process? What if I use this technique? What if I make use of this reference?” Think of the “Mad Libs” fill-in-the-blank style of creation: ___ is a ___. Once you reach a formulaic structure like that, you are ready to iterate properly, because now it’s possible to play around with the details.

There are lots of formulas, and you can oftentimes choose which ones you want to work with. There are formulas for drawing human figures, formulas for writing pop songs, formulas for building houses and calculating budgets. Sometimes the iteration quest is primarily about finding the formula you want to use. But unless we’re referring to a purely technical problem, neither do you always have to use formula structures as if they were laws. You can merely allude to them, and write around them as convenient.

The thing that stops iteration cold is filtering too early just because you can’t see it fitting back into the larger work. Don’t do this while you iterate — allow the weird and unlikely stuff in. It takes practice to let go like this and stop saying “no”.

After I’ve rolled the dice by doing iteration, I now have focus points. Something happened in those sketches or variations, and now I have a new set of ideas to work with that were not there in the original brainstorm. The new ideas necessarily include parts of the old ideas, and while some of them are, in fact, unusable and best off being archived for future reference, a substantial number will still fit in with the overall goals.

And so a new round of development begins, starting from the new focus points and building on those. This is how leverage is created: Because a new focus generally represents the work better, it adds clarification to every other part of the design. When you return to the larger work after having iterated on parts of it, it will snap together like Lego blocks, at least until you hit the part you didn’t iterate on. But then you’ll know what to do…