Marshmallow reviews Fail, Fail Again, Fail Better: Wise Advice for Leaning into the Unknown by Pema Chödrön

The book bunnies are back! Today in her first review for the new 2025-2026 season, Marshmallow is writing about Pema Chödrön’s short but impactful book, Fail, Fail Again, Fail Better: Wise Advice for Leaning into the Unknown, published first in 2015.

Marshmallow’s Quick Take: If you like books about self-improvement, contemplation, and dealing with challenges, then this is the book for you!

Marshmallow’s Summary (with Spoilers): The book starts with a foreword by Seth Godin, in which he introduces an interesting phrase from the author: “getting all the frogs in the bowl.” This essentially means that, despite all efforts, if you’re trying to get frogs to stay in a bowl, there will always be some that hop right out–which I presume is a metaphor for the occasional, unavoidable failure. He describes his own past with failure, citing the plethora of publishing rejections he experienced. But Chödrön, he says, teaches one how to dance while the frogs continue to jump. This piqued my interest.

Godin also mentions the “infinite game” (one you play not to win, but simply to play). He ties this into the jumping frogs, claiming that perhaps the jumping frogs are the point, rather than the orthodox objective of just getting them to sit still in the bowl. I found this point a little more difficult to tie into the objective of the book. Rather than focusing on how to grow from failure, it suggests that the entire purpose of existence is failure. I felt that this is a separate thesis that is harder to defend. But the foreword made me excited to start. 

The central core of the book is derived from a speech Chödrön gave at her granddaughter’s college graduation. In it, she explains that she wasn’t sure her topic choice would be appropriate since preparation for failure (her topic choice) is superfluous–teachers and students hope–if one is taught to avoid mistakes in the first place. Yet, she says that the “fine art of failing” may be the most important lesson that these new graduates will learn in their entire lives.

Most of her speech centers on the topic of “welcoming the unwelcome.” Through this, Chödrön explains, one can turn towards their pain and their failures and learn from them by letting go.

Chödrön describes the two main responses we have towards failure: we often blame other people or other factors for it, and we almost always begin to experience some sort of self-identification with failure. The author describes how she hit rock bottom after leaving her second husband and found guidance with the founder of the college she is speaking at, Chögyam Trungpa Rinpoche. She also recounts an old story which I found fascinatingly eye-opening. The speech then ends, and rather abruptly, but she delivers her message effectively and really does not need to say much else. 

The third and final part of this book is an interview with the author conducted by Tami Simon. This section really goes way deeper on all the ideas introduced more briefly in the speech (which was shorter and interspersed with little calming illustrations). 

Marshmallow’s Review: I found this to be a very engaging book. I agree with many of the ideas, and actually found that some of my own ideas appeared in this book. The author certainly has many novel, wise suggestions and is clearly trying to make the world and the reader better. I liked how the solution presented is more about addressing the pain of failure rather than how to prevent it because there are many amazing books about that too (see for example all the books by Cal Newport that I have already reviewed for our blog). But overall, the speech itself is like a calm, easy-to-read intro to the ideas that are expanded more in the interview.

I thought this was a very intellectually and emotionally engaging book. Overall, Fail, Fail Again, Fail Better: Wise Advice for Leaning into the Unknown is short, but engenders deep contemplation that will last for a long time.

Marshmallow’s Rating: 98%.