To Avoid getting stuck, one can to Break problems down into easier problems. When it comes to writing, one can Write small, self-contained notes, but that is not enough. A book contains many ideas, and has to be comprehensible to readers, not only the author. This introduces many new problems, the first one being how to arrange all those hundreds of ideas into a coherent structure. This can’t be done all at once. Ideas are related in all sorts of ways, and it’s a creative challenge just to figure out the order in which to present two ideas, much less hundreds.

Moreover, a book is not just the concatenation of existing ideas in the proper order. Some ideas will appear in multiple forms in multiple places. Some will be dropped. Some will be elaborated upon with background knowledge and helpful examples. New ideas will be introduced, and old ideas expressed anew, in the process of writing a manuscript others can read. The process of integrating all these ideas will turn up unforeseen conflicts and problems between ideas which hadn’t been considered together in such detail before. Trying to express an idea clearly and succinctly requires understanding it well, and making it sharper, and this can lead to all sorts of new ideas, and changes to old ones.

These are all problems of substance, but there are also problems of communication - of language. That is another layer of problems - creating sharp sentences, paragraphs, pages, and chapters. Putting things in perspective - emphasizing what is most important, and sequencing things so they are easy to understand, and one is exposed to one idea only after prerequisite ideas have been introduced.

In other words, a books’ worth of ideas is not a book. Making it into a book (or essay, or whatever) will introduce many new problems (in the good sense of the word, not necessarily distressing ones). Problems of substance and of communication. If you cannot break these problems down to a manageable size, you cannot write the book. You’ll get stuck.

So, how do you break these problems into a manageable size? What are the problems?

The curse of knowledge - providing the relevant background knowledge and context for others to understand not only what you are saying, but why it is important and interesting.

Basic clarity and concision - creating clear sentences, using the right words.

Coherence and continuity - making things flow from one sentence to the next.

Making things tractable for the reader - chapter titles and section breaks allow the reader to skip around, and to find and refer to sections they care about, to recall what they’re read.

The problems of structure and modularity - understanding the ideas at various levels of abstraction. The high-level patterns and relationships. Some ideas are more important than others, more high level, more fundamental, whatever. Some ideas belong in a certain sequence, or in a certain group. Maybe they are part of the same topic or argument. Just like pages allow you to make small, self-contained chunks, you need to create chapters and outlines and other things to create small (relative to the size of the whole book), self-contained chunks. Just like with notes, that is nontrivial and creative.

What about Chunk ideas into manageable groups using outlines?