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What to Do When You Get Stuck Writing

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It's widely said that methodologies like Zettelkasten make writing easier, but even with them, writing is still hard. Because the materials are already given, starting to write and structuring the content get easier, but writing the details is still difficult. In fact, I think the difference between good writing and mediocre writing lies in the details. Whether a piece is persuasive and engaging is decided by those details.

Whether I'm writing a newsletter or a book, I've felt that psychology of getting stuck many times. I felt it especially keenly during my master's thesis. When you get stuck in the middle of writing, you feel uncomfortable and anxious. Your mouth is shut tight and your eyes glaze over. You just stare at the monitor. Your hands hover frozen over the keyboard, tapping now and then. And to escape that discomfort, you sometimes flee to social media. I suspect many people have felt this.

This phenomenon is called writer's block. To solve it, I read all kinds of articles and ran experiments. As a result, I found that most of the methods rest on one common principle.

That principle was "remove constraints when you diverge". Most knowledge work is divided into a divergent phase and a convergent phase. Removing constraints during the divergent phase is a principle that applies to all knowledge work. A typical example is brainstorming, where criticizing other people's ideas is forbidden during the idea-collecting stage. The moment there is even a little criticism, coming up with ideas shrinks back, and that blocks the collecting of ideas.

Collecting fleeting notes in Zettelkasten, or dumping whatever comes to mind into the Inbox in GTD, is likewise meant to remove constraints during divergence so that gathering thoughts and materials goes smoothly. I've also made a video about this.

Writing is no different. Writing is also divided into divergent and convergent phases, and when you get stuck, it's usually because you're putting constraints on yourself during the divergent phase. Self-censorship is what keeps the words from coming. To use a metaphor, it's like pressing the accelerator and the brake at the same time. So if you apply the principle "remove constraints when you diverge," writing becomes a bit easier.

The principle is just one, but there are many ways to put it into practice. Below, I introduce the ways I've put "removing constraints during divergence" into practice in writing. I'm confident they'll help right away.


1. Force Yourself to Write Anything

Just write wildly. You can write about the topic you're supposed to be writing on, or you can put down whatever thoughts come to mind. This is actually a technique called Freewriting (freewriting). You could also see it as a warm-up. As you force yourself to write whatever comes to mind, your head starts to feel warmed up, and the writing begins to flow.

You can also use a tool. The site Word Sprints↗ pushes you to write as many words as possible within a time limit. On Word Sprints, you can aim to write as much of your piece as you can in the allotted time. With that goal, you can put writing ahead of self-censorship. It's much easier to diverge recklessly first and polish the writing later during revision. The accelerator and the brake should be pressed separately, not at the same time.

Also, you don't have to write in order. Start with the part that comes to mind. There's no need to write straight through from introduction to conclusion. If a conclusion comes to you vividly, write the conclusion first. In fact, when we decide to write about some topic, what we often have is not an outline of the whole piece but one vivid part of it that we want to put down.

If you start with the parts that come to mind and grow the overall volume of the piece this way, the anxiety of being stuck will fade. After all, you now have a piece of writing, and you're much closer to finishing it. Part of the relief also comes from a bias toward action. Less anxiety frees you from tunnel vision, which helps you write better.

2. Write by Speaking

If you write as though you were talking to someone, writing comes more easily. For expository pieces, it helps to imagine someone in front of you and write as if you were explaining it to them. It feels like there are fewer constraints when speaking than when writing. People make slips of the tongue, but you rarely hear of slips of the pen. It's easier to be careless when talking than when writing (?)

Writing as if you were explaining to someone not only increases the volume but can also, unexpectedly, reveal gaps you hadn't thought of. You're speaking in order to persuade or explain to this person, and that's when you notice leaps in logic or explanations that fall short.

Speech-to-text (STT) can help in this process. As of 2026-09-29, I'm using a tool called Wispr Flow. Its recognition is quite good: when I speak, it converts my words into text in Korean or English.

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