We often discuss art this way: the artist had something he wanted to express, and then he just, you know, expressed it. That is, we buy into some version of the intentional fallacy: the notion that art is about having a clearcut intention and then condently executing same.

The actual process, in my experience, is much more mysterious and beautiful and more of a pain in the ass to discuss truthfully.

When we start reading a story, we do so with a built-in expectation that it will surprise us by how far it manages to travel from its humble beginnings; that it will outgrow its early understanding of itself. (Our friend says, “Watch this video of a river.” The minute the river starts to overflow its banks, we know why she wanted us to watch it.)

So, why the index cards, on that date? In a word: underconfidence. We prepare those cards and bring them along and keep awkwardly consulting them when we should be looking deeply into our date’s eyes because we don’t believe that, devoid of a plan, we have enough to offer. Our whole artistic journey might be understood as the process of convincing ourselves that we do, in fact, have enough, figuring out what that is, then refining it.

So if your primary goal is to have a fully worked out, set-in-stone plan, you are only upping your chances of being unoriginal. Moreover, you cannot plan your way out of problems. While planning is very important, and we do a lot of it, there is only so much you can control in a creative environment. In general, I have found that people who pour their energy into thinking about an approach and insisting that it is too early to act are wrong just as often as people who dive in and work quickly.

We hedge all the time. We note that we think something will work, that a solution could be effective, or that an alternate approach might work better. We suggest that something seems like a good course of action or that, in our opinion, something else is worth trying.

But without our realizing it, hedging can undermine our impact, because while we’re sharing our thoughts or recommendations, by hedging, we’re simultaneously undercutting them. We’re suggesting that we’re not sure those thoughts and recommendations are worth pursuing.

The interview reminded him about his broader situation and the things he had to do to move forward. He was essentially reminded of his “list” and various priorities during our conversation.

Making a list is a basic tool for overcoming our own cognitive limitations. The list itself counters forgetfulness. The act of making a list forces us to reflect on the relative urgency and importance of issues. And making a list of “things to do, now” rather than “things to worry about” forces us to resolve concerns into actions.