[driggs]

The obvious second book to read after Laozi is Zhuangzi (Chuang-Tzu). His book is a joy to read, full of humor and anecdotes, where Laozi's reads like cryptic poetry. Both books describe a common worldview of harmonious living with the natural world, from complementary perspectives.

I personally recommend Burton Watson's translation of Zhuangzi.

[franksvalli]

Trying Not To Try by Slingerland is a great accessible introduction to the different modes of Chinese philosophy, and the two approaches to Daoism by Laozi and Zhuangzi are discussed.

For more depth I highly recommend Van Norden's Introduction to Classical Chinese Philosophy. I took a course that used this book as its text and it was really life changing and made me hopeful that there are some more practical philosophies out there for us.

[mcguire]

I personally like Angus Graham's translation, Chuang-tzu: The Seven Inner Chapters and Other Writings from the Book Chuang-tzu, as well as his essays on it, A Companion to Angus C. Graham’s Chuang Tzu.

For one thing, it gave me some significant sympathy for analytic philosophy for the first time.

[juris]

Seconding this-- and I can recommend the Merton translation. Great for late night reading, or if you are feeling especially unsettled.