While I don't think it's necessary to read a book 100 times in order to understand it (see [[Approach To Reading 1]]), I do think you'd be hard pressed to read a book 100 times and not understand it.
There are some important caveats to this approach that should be mentioned.
- This approach works best with difficult-to-digest philosophy books (such as The Tao Te Ching). The repetition will slowly make the material more intuitive and personal
- Rather than actually reading the book 100 times, I think it's better to listen to an audiobook.
- This approach works best for short works, where the audiobook isn't much more than an hour in length.
- After some number of listens, it's probably a good idea to do an actual reading of the book. This reading should be done slowly, with lots of notes taken and time spent contemplating and perhaps writing about the material. After that reading, go back to listening to the audiobook for the remainder of the 100 listens.
- It may be beneficial to continue your listens past 100, but that's up to your own judgement.
The reason for doing multiple listens before reading/analyzing the book is that it allows you to become more familiar with the text, and removes some ambiguity from otherwise difficult passages. This should make your analyzation more fruitful than if you had started out with a reading.
Additionally, doing a deep analyzation of the book after becoming somewhat familiar with it will open your eyes to its meaning even further. No amount of reading will give you the same understanding as deep contemplation, so this step is absolutely necessary.
Further audiobook listens after doing your analyzation will be more helpful, because your understanding of the text will be much greater than it was before.