His first three books form a kind of trilogy, although they can be read independently: the first is Hearing God: Developing a Conversational Relationship with God (previously titled In Search of Guidance). The second is The Spirit of the Disciplines: Understanding How God Changes Lives. And the third is The Divine Conspiracy: Rediscovering Our Hidden Life in God. He has also written a stand-alone book entitled Renovation of the Heart: Putting on the Character of Christ. These are obviously not books defending Christianity, they are books written for people who already accept Christianity. If you are a Christian, I cannot recommend them strongly enough. Here are some of his shorter writings on Christianity, and here are some of his shorter philosophical writings. There's some overlap between these two sections.
My introduction to Dallas Willard's writings was Hearing God. Part of the idea here (although he doesn't say it in so many words) is that your "inner monologue" isn't really a monologue; not all of those thoughts originate with you. The goal is to learn to identify when it's God speaking, when it's just your own subconscious, when it might be other spiritual voices that may not have your best interests in mind, etc. For me, this was revolutionary. I was very suspicious of this claim, so the fact that it came from someone who's clearly a critical thinker and an expert logician assuaged much of my concern. In fact, it brings to mind C. S. Lewis's statement in The Problem of Pain,
If your thoughts and passions were directly present to me, like my own, without any mark of externality or otherness, how should I distinguish them from mine? ... You may reply, as a Christian, that God (and Satan) do, in fact, affect my consciousness in this direct way without signs of "externality." Yes: and the result is that most people remain ignorant of the existence of both.
Dallas Willard's most recent book is a collection of essays entitled The Great Omission: Rediscovering Jesus' Essential Teachings on Discipleship. The title is a take-off of the Great Commission, the command of Jesus to go into all the world and make disciples. What is sometimes omitted in this is the next verse, "teaching them to obey everything I have commanded you", which is, after all, the goal of discipleship. I haven't bought this book yet, although I plan to. I just realized, however, that most of the chapters are actually available as articles on his website. So as a sort of advertisement, I thought I would present the table of contents of The Great Omission with links to those chapters that can be read online. This isn't meant to dissuade you from going out and actually buying the book -- on the contrary, as I've said before, I can't recommend reading his books strongly enough.
The first chapter is also the second appendix to Spirit of the Disciplines. The last section is (apparently) excerpts from a few of the great writings on discipleship from Christian history. I've provided links if they are available on the Internet.
Section I: Apprenticed to Jesus
1. Discipleship: For Super Christians Only?
2. Why Bother With Discipleship?
3. Who Is Your Teacher?
4. Looking Like Jesus
5. The Key to the Keys of the Kingdom
Section II: Spiritual Formation and Development of Character
6. Spiritual Formation in Christ Is for the Whole Life and the Whole Person
7. Spiritual Formation in Christ: A Perspective on What It Is And How It Might Be Done
8. The Spirit Is Willing, But… The Body as a Tool for Spiritual Growth
9. Living in the Vision of God
10. Idaho Springs Inquiries Concerning Spiritual Formation
11. Personal Soul Care: For Ministers…And Others
Section III: Discipleship of the Soul and the Mind
12. Spiritual Disciplines, Spiritual Formation, And The Restoration Of The Soul
13. Christ-Centered Piety
14. Why?
15. Jesus the Logician
Section IV: Books on Spiritual Living -- Visions and Practices
16. Letters by a Modern Mystic by Frank C. Laubach
17. The Interior Castle by Teresa of Avila
18. Invitation to Solitude and Silence by Ruth Haley Barton
19. When God Moves In: My Experience with Deeper Experiences of Famous Christians
20. A Room of Marvels by James B. Smith
A Parting Word: "As You Go…"
Update (April 8): I fear I was misleading about the content of Hearing God. The point above, about how our inner monologue may actually be a way that God communicates to us, is correct and important. But one of Willard's main points in that book is that hearing God is just one part of an overall life with God. One can't live as if she were her own person, but then try to "listen" to God when she wants some advice. If someone ignored you except when they wanted something from you, would you accommodate them? Why would we expect that God would?
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