Thinking in writing is a monologue with yourself- or, in that case, dialogue. The main problem of this format is that that dialog is chaotic and very fast. Nobody can follow those jumps from some peace of information to the next association. That's why it is hard to evaluate or backtrack the logic that brought me to the current point (some decision or current place where I have to slow down or stop for now and not forget where I stopped).
Problems of thinking in your head
Very fast to keep track.
I cannot validate the result.
You have limits on working memory.
Types of thinking in writing
Free writing
The best way to overcome procrastination is to write down every thought. Sometimes, you don't know where or how to start. One recommendation would be: "Just start writing down every thought you have..." That can work and be very productive for getting into the *flow* state.
The risks here are that you can quickly fly away into dreaming or follow your emotions and lose track of your initial goal. So, it could work well for short tasks. But it's a great tool as the initial trigger for writing more of your thoughts. It also could be used as the first raw draft for the next iteration over text - editing.
Structured writing of your thoughts
Here is another way to approach writing down your thoughts: by putting some structure (steps) around our always-minded mind.
Goal/Question
I was getting to this idea for quite some time - to get into free writing intentionally. You will still have some topic/question/context that you want to write about, so why take it as an entry and use a checklist? Start by writing down a question or thesis you like to consider. It can be your opinion about something or what you know or think about some question. It will help your brain keep on track for the whole writing session (this is where the Pomodoro Technique - Wikipedia will benefit you).
Consider which points need to be covered from the beginning, so your writing will reach a logical conclusion. This will be your outline.
Filling
This is where being constrained by Pomodoro allows you to give yourself the freedom to let your mind go for a ride. Since it will be the first raw version, you can put all you have before editing, allowing some exciting ideas to come from your brain. And if the timing enables you to have some breaks (not just time between Pomodoro but longer, like days), your brain will get even more engaged by writing on this topic.
Review and editing
After spending time on this text, you become an expert on this topic (after multiple amounts of Pomodoro). It's a great time to zoom out and look at the whole structure of your text. Is it still getting where you want to be at the end of writing this text? The goal here is to make sure your mind does not go very far from the main topic and, if necessary, move stuff around. Or, if some points become unnecessary, delete them.
Your text is ready!
Our main goal is to have repeatable practice with a checklist (one day, I will read you The Checklist Manifesto: How to Get Things Right: Gawande, Atul). And follow the natural thinking processes of your brain just by putting some constraints on thinking.
This post results from thinking in writing, triggered by personal curiosity and a blob post. I was trying to answer the question: “What do I think about structured thinking in writing?”.