Phenomenal Books Revisited: FALLING UPWARD by Richard Rohr

Spotlighting books I return to repeatedly as they contain abundant, applicable, evergreen wisdom.

For this inaugural Phenomenal Books Revisited (PBR), I could have helped myself by choosing a title that is not my all-time-number-1/desert island/if-I-could-only-have-one-book-for-the-rest-of-my-life book. But I’m going for it. While there are many incredible books I will joyfully highlight in this PBR series, the one book I’ve read, re-read, reviewed, consulted, listened to and recommended more than all others combined is Falling Upward, by Richard Rohr. It’s only a modest exaggeration to say that when I revisit my highlighted passages, I revisit ~90% of the book. I’ve never before or since read something that felt more like it was written to and for me individually. Falling Upward entered my awareness at the time it was most needed.

The Premise

Richard Rohr defines and explores deeply what he terms the two halves of life. These two halves, or phases, of life are not chronological or age-based, but rather based on one’s approach and attitude towards life — one’s way of seeing and being in the world. In the first half of life, one is busy learning how to be an individual, a successful person. Defining your identity, determining strenuously and leaning heavily on what you feel you are and are not, making yourself significant and superior to others are the dominating objectives of the first half of life. “Building your container,” as Richard describes it, is the main goal.

By contrast, the second half of life is all about “the contents of that container.” The second half is encouragingly described as “the further and fantastic journey,” the phase of life in which all of those rigorous definitions, separations, and hard-boiled opinions about everything can give way to a profound, enduring joy that simultaneously includes and transcends all that came before. Though Richard suggests that it’s not unusual for some to make the transition between the two halves of life between their mid-30s to mid-50s, he freely shares how he’s met many young children, especially those afflicted with serious life situations, who’ve progressed to the second half or phase of life. Similarly, he’s met many senior citizens who sadly remain stuck in the first half of life, hardened and clinging to their biases and well-worn opinions, likes/dislikes, and hatreds. As Richard at times laments, “We live in a society with elderly people, but very few elders.”

A point Richard makes so skillfully, the point that fuels the title of the book, is that it’s practically impossible to plan, attain, or achieve your way into the second half of life. Most people, if they get to the second half at all, somehow must FALL their way upward. Something significant — what Richard suggests is most often either great love or great suffering — must occur in order to break the ego of its imagined winning streak of feeling separate and superior. “We come to God not by doing it right but by doing it wrong!” Richard often encourages. This, perhaps more than any other message of this book, inspires me the most. This book is not about what you need to do or learn, but rather about how to let go; how to unlearn what is no longer helpful or necessary. The guidance is relinquish the habits, opinions, and (false, illusory) sense of control limiting you from entering the best, the second, part of life.

Richard teaches that the the first half of life is not bad or wrong. It is a necessary, functional. It also just happens to be supremely limiting for those remaining in it their entire lives. In “Falling Upward,” Rohr beautifully describes and maps the journey from the first to the second half of life, painting pictures of the destination in ways that make it aspirational and attainable.

Three Inspiring Takeaways

Out of the dozens+ instructive, motivating insights in this book, here are three I’ve found to be most impactful:

The second half of life is not a pleasant epilogue. Not a nice-to-have coda. Not an after party. It is the main purpose of life. The main event. “The first half of life is discovering the script, and the second half is actually writing it and owning it.” Such quotes underpin what I’ve found to be a highly motivating premise of this book: for those stumbling, encountering, falling disarmed into the second half of life, the most profound and purposeful part of life is still to come. Your best days are ahead of you!

So much of our modern, predominantly western culture projects the message that once one’s intensely productive, earning and/or child-rearing years are over, the main thrust or purpose of life is over as well. Even with the millions of images and ads featuring people in mid-life+ doing all sorts of fun, active, interesting things, there’s a subtle subtext to those images that suggests these people reached their finish line — they peaked — and are now free to chill, spend, and relive.

There’s nothing wrong with enjoying the fruits of one’s life, but how much more inspiring it is to know that there’s more and better fruit to cultivate! “So get ready for a great adventure, the one you were really born for,” Richard says in the introduction. With this quote he plants an early seed as to how the second half of life can be — and is, for those who embrace it wholeheartedly — a venue for the most fulfilling, purpose-driven parts of life.

You have a “loyal soldier.” And it’s time for that soldier to be thanked and discharged. Just after World War II, in response to Japanese soldiers returning to their communities and families emotionally ill-equipped to fulfill their civilian roles, village elders created a formal ceremony to thank each soldier and express how it was now time for them to put away their war-honed instincts and become calm, trusted, needed members of their community. This story and Richard’s concept of “discharging the loyal soldier,” is a central metaphor and powerful concept of this book. Our “loyal soldier” represents our collective habits, assumptions, defense mechanisms, biases, absolutes, personality strengths and quirks that helped us build our container in the first half of life, attributes forged in the cauldron of our earliest needs and experiences. Our inner loyal soldier was necessary to get us to where we are now, yet is also emblematic of the very things holding us back from transitioning into the second half of life, a time in which softness is far more useful than hardness, openness far more necessary than close-mindedness, finding common ground infinitely more satisfying than standing apart.

“When you first discharge your loyal soldier, it will feel like a loss of faith or loss of self. But it is only the death of the false self, and is often the very birth of the soul.” Richard devotes a good chunk of the book to teachings such as this. On a highly personal level, the loyal soldier metaphor helped me to frame, understand, and begin to transform a handful of strong, persistent attributes that, until this book, had just sorta “stopped working” for me, seemingly for inexplicable reasons.

Ways to know you’re entering the second half of life. When you no longer feel it necessary to stand out or stand apart. When you love what you have and not crave the next new thing. When you no longer feel you have to prove your worthiness to yourself or others. When shared qualities are more nourishing than differences. When you feel at ease in situations that used to enthrall or enrage. When you can move forward without feeling the need to disparage or discard all that came before (ie, “include & transcend”). When you no longer compare yourself to others.

These are just a handful of the guideposts Richard offers on the journey. The book is filled with them, all delivered in Richard’s inimitable style of avoiding absolutes, if/then statements and black/white thinking. His teachings serve as both aspiration and yardstick.

Favorite Quotes

“We grow spiritually much more by doing it wrong than by doing it right.”

“[In the second half of life] your concern is not so much to have what you love, but to love what you have.”

“The best criticism of the bad is the practice of the better.”

“Soulful people temper our tantrums by their calm, lesson our urgency by their peace, exhibit a world of options and alternatives when all conversation turns into dualistic bickering.”

“Most people do not see things as they are; rather they see things as they are.”

“We may spend our whole life climbing the ladder of success, only to find when we get to the top that our ladder is leaning against the wrong wall.” (ref. Thomas Merton)

“God comes to you disguised as your life.” (ref. Paula D’Arcy)

“We have only to follow the thread of the hero path. Where we had thought to find an abomination, we shall find a god; where we had thought to slay another, we shall slay ourselves; where we had thought to travel outwards, we shall come to the center of our own existence; where we had thought to be alone, we shall be with all the world.” (ref. Joseph Campbell)