PAUL GRAHAM IS the co-founder of famed startup incubator, Y Combinator, which invests in and has produced many successful companies. They include some of which you might have heard of, such as Stripe, Airbnb and Dropbox. He is also the author of Hackers and Painters: Big Ideas from the Computer Age, and has frequently published his essays online at his personal website.
The full piece which contains the quoted text above is a quick-fire, high-impact note, which somehow manages to pack in a book's worth of writing advice into a beast of an information-dense, 380-word sentence.
In this related essay of his, PG dives deeper into what writing an essay should look like, and shares more about his thoughts on the use of writing as a thinking exercise for refining one's ideas.
The Main Takeaway
Amongst other arguments and gems of advice in this mini-essay of his, PG's main point argues that writing serves as an exercise for the author to not only refine their ideas, but to also come up with new and better ones entirely.
This is contrary to what might perhaps be considered a traditional view of the purpose of writing, which is that it serves to merely communicate one's preexisting ideas.
Obstacles and Difficulties
It involves a lot more time and effort to evolve one's thinking through the act of writing, than it is to merely write something down to commit your thoughts to paper. Using the post from his quoted text as an example, PG spent 23 minutes writing the original version of the post, and spent almost double that time — a further 44 minutes rewriting to get it to its current form.
Despite (and probably because of) the additional effort involved, the resultant work is that much more insightful and noteworthy.
Using an Outline
Having a detailed outline from the outset could prove counterproductive to that endeavour, forcing a writer to stick to the prewritten manuscript, and not being allowed to meander from the original plot.
With regards to the quoted text above: PG isn't stating that we shouldn't use outlines in our writing. Instead, he's trying to encourage writers to write as a freeform exercise, using your written words to be fluid in your thinking, exploring and refining the ideas you have on your mind.
Hence, the outline of your written work evolves with your thinking as you go along improving on your mental model of the subject at hand. The result could be a conclusion that wasn't in your thoughts to begin with, and could even prove to be a surprising finding that you didn't expect.