When I first started writing, I struggled with the most important part of being a writer: Sitting down, marshalling my thoughts, and actually doing the hard work of writing. All of the writers I admired seemed to regularly generate new, creative ideas—articles for humour publications like McSweeney’s and the New Yorker, spec scripts, sketches, journalism, etc.—while it often took me months to complete a single article or sketch.
Then one day I learned something even more discouraging: the writers at my favourite publication, the Onion, were expected to generate upwards of 20 article ideas per week, 95% of which were eventually discarded. I had never thought of twenty good joke ideas in my life, much less thrown away that many. How was I supposed to become a professional comedy writer while crawling along at a rate of several ideas a year?
After my initial shock subsided, I decided that I’d put myself on a similar Onion-style regimen and force myself to write down a list of 20 joke ideas a week. This result of this experiment impacted much more than my volume — indeed, my entire creative process:
At first, trying to fill the 20 idea quota was excruciating. For days, I was consumed by writer’s block. Then, one afternoon, I felt a burst of creativity and wrote down three ideas at once. In my first week, I managed to write down a list of eight new jokes.
It didn’t feel like I was working particularly harder than I was before. For the most part, I was doing what I had usually done before starting the experiment: walking around, going to work, sitting in cafes, etc. The only difference was that now, I had a container for all of my ideas to fall into. Ideas that I might have dismissed or simply forgotten to write down were now diligently captured.
This often meant that the ideas on my list were incomplete—a snippet of dialogue here, half a headline there—but they were better than nothing, and often became starting points for larger ideas. The point is that once you open up those floodgates, the ideas really do begin to flow: inspiration strikes more often and from new and unexpected places.
Related: Want to learn more about brainstorming techniques? Check out this video with Matt Di Paola, Managing Director of Innovation for Toronto Creative Agency Sid Lee:
A few weeks into my experiment, I realized that the only way I was going to hit my 20 idea quota was to completely relax my expectations and write down every single idea that came to mind, without any judgement. Writing out long lists of ideas, I was quickly learning, was a lot less about forcing myself to write and more about getting rid of any mental obstacles that might be hindering the free flow of ideas.
I wasn’t having trouble with output because I didn’t have any ideas: my problem had been that I was too picky and judgmental with my writing, causing myself to nip every idea in the bud before it could be fully expressed. Relaxing my expectations not only immediately increased the flow of creative ideas, but also made me less anxious when it came to sit down and flesh out an article or sketch.
Before starting this experiment, all I had had was the last good idea I had come up with. Admitting that an idea was bad and trashing it—especially after I had spent weeks working on it—was terrifying. Now, I was less invested in individual pieces of writing, and more confident about moving on once it became clear that an idea wasn’t working out – confident that there were many more ideas worth exploring.
Knowing that I had a large reserve of other ideas waiting to be explored and fleshed out made me both more excited to start working on new ideas — and more forgiving with myself once it was clear they had run their course.
My experiment with long lists wasn’t just making me a better writer—it was also making me a better collaborator. At the time, I was a writer at my university’s humor magazine, which has its own weekly Onion-style pitch meetings where writers would get together to workshop each other’s ideas.
A few weeks into the experiment, I noticed a marked difference in the way I approached brainstorming in a group. I was less protective of my own ideas, more open to criticism and eager to collaborate with others. I was also more willing to take risks with my jokes and also took things less personally when they didn’t land.
Being precious about my ideas, I slowly realized, was one of the worst traits I could have as a comedy writer. Long lists were helping me overcome this instinct by making me less invested in my individual ideas and more interested in writing as a process.
Maybe the most valuable lesson that long lists taught me was that a large majority of the ideas that came out of my brain — upwards of 95% — were terrible ideas, but that this is okay. Because this was true for everyone else as well.
A friend of mine who worked in advertising told me that copywriters at his agency often came up with their best material by forcing themselves to write out long lists of ideas and then throwing away most of what they thought of. One local agency in the city had a mantra about brainstorming and lists: “Your best ideas are your first idea and your hundredth idea.” Journalists that I talked to about this showed me Google docs filled with hundreds of rejected story ideas.
The most successful writers, I began to learn, weren’t the most talented, the most creative, or even the hardest working ones. What really determined success in writing was the ability distinguish the good ideas that your brain produces from the ocean of bad ones it churns out.
Long lists forced me to start doing precisely this: to put all of my creative ideas to paper where I could see them, rather than leaving them to float around in my brain, and to start the slow and difficult process of manually sorting through the bad ones to get to the good ones.