Unlocking the Zen Koan: A New Translation of the Zen Classic Wumenguam has been helpful. Also, reading Red Pine's translations and commentary on the The Platform Sutra: The Zen Teaching of Hui-neng, Heart Sutra and Diamond Sutra. Although many people speak of the influence of the Lankavatara on Zen, I find it very difficult to read, even Red Pine's fairly approachable translation. But, the idea of "no views" and "no perceptions" was helpful, and "to speak of [this] to to speak of not [this]". Those themes come up often in koans. And studying Lao Tsu helps. Despite what the "not zen" crowd says, a background in Mahayana Buddhism and Taoism, and some historical background really does help a lot. Currently reading Ordinary Mind as the Way: The Hongzhou School and the Growth of Chan Buddhism and The Hongzhou School of Chan Buddhism in Eighth- through Tenth-Century China to get some background on Mazu's lineage. Like many westerners, I used to think koans were just about derailing rational thought. While that is useful, now I also see some patterns, a certain amount of "sense", and more experiences of "of course". Easier koans like, it is your mind that moves help with the more difficult ones. Another helpful one is What are you doing? What are you saying?.

u/ludwigvonmises · 1 point r/zen

I always recommend engaging with primary source works (translated, naturally...), but some people are not ready to grapple with Yuanwu's collection of koans or with Linji yet.

Some initial works to start out:

The Way of Zen, by Alan Watts
Buddhism is Not What You Think, by Steve Hagen
The Taoteching (the Taoist classic - Taoism is the mother of Zen)
What the Buddha Taught (a primer on classic Buddhism - Buddhism is the father of Zen)
Headless experiments inspired by Douglas Harding

If you've worked through (one or more of) those and want more, some primary works I recommend:
The Zen Teaching of Bodhidharma
The Platform Sutra, by Huineng the 6th Patriarch of Zen
The Zen Teaching of Huang-Po

That will get you to a good level.

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