Falling Upward for Leaders
For the past ten years, I’ve been using Falling Upward as a textbook for executive coaching with leaders. I had been wondering how to bridge the gap between Fr. Richard’s teachings and the fast-paced, pressurized pragmatism of organizational leadership. But when I first read Falling Upward, my favorite of Fr. Richard’s books, I realized that this was a key text in helping ‘translate’ Richard’s profound insights to a wider audience.
Employing Carl Jung’s ‘morning and afternoon of life,’ and renaming it the ‘two halves of life,’ is the first genius of Fr. Richard’s book. This sublime metanarrative for life gives permission to experienced, senior leaders to take the foot off the gas and consider the youthful push and drive, the cut and thrust, that has so often played a formative role in who they are as a leader.
From college to sports, volunteering, military service, and the arts, the early adult years of so many leaders I’ve worked with was focused on performance, activity, and pushing to achieve the next goal. Their dopamine systems have been reinforced to relentlessly pursue ‘the next outcome’; be it an MBA, early-career exposure to significant responsibility and reward, or a coveted corner office. Seeing that all of this ‘great pursuit’ was a fundamental and important part of the first half of life can come as a relief, most especially to leaders who are burning out, disillusioned, or wondering why they committed so much time and energy to climbing each rung of their career ladder. Many are in mid-life, only beginning to count the cost of the familial and health trade-offs their first half of life has entailed. They realize that ‘Our institutions and our expectations, including our churches, are almost entirely configured to encourage, support, reward, and validate the tasks of the first half of life.’[1] Tasks in which they have excelled. But now there is something in their life experience, or their leadership context, that no longer fits this mold. They realize, with the benefit of hindsight, that, ‘When you are in the first half of life, you cannot see any kind of failing or dying as even possible, much less as necessary or good.’[2]
So what’s next? Is there an alternative narrative to that espoused by much of organizational life, of ‘growth for growth’s sake’? When leaders begin to accept that ‘The supposed achievements of the first half of life have to fall apart and show themselves to be wanting in some way, or we will not move further’,[3] some significant “soul” work can begin. As Fr. Richard dangles the possibility of a second half of life before them, many leaders find an alternative nearly impossible to envision. They are approaching this ‘afternoon of life’ with a dualistic mind, and thus they lack the lenses to see what it might entail. A deconstruction, a purposeful ‘disordering’ must first take place. And this is where Fr. Richard’s inclusion of the Hero and Heroine’s Journey comes in as the second stroke of genius in Falling Upward.
So much research has gone into the stories that leaders tell themselves. Their “mythology”, how they frame and reframe the narratives of their leadership is what fundamentally shapes the trajectory of the leader they become. Fr. Richard’s summary of the Hero and Heroine’s journey is a clear framework for understanding the cyclical nature of change and growth through loss and rebirth. He makes much of the psychological shifts that everyone encounters in this descent towards death, where the ego must die. For this to happen, the personas that leaders have cultivated must be exposed and befriended so that they can be transformed into the second half of life. The ‘persona…your stage mask is not bad, evil, or necessarily egocentric; it is just not “true.” It is manufactured and sustained unconsciously by your mind; but it can and will die, as all fictions must die.[4]’ For leaders, these personas might include their qualifications, their experience, their successful projects, and campaigns, what they’ve written about, what they are known for on the speaking circuit or simply just the tagline of their LinkedIn bio. All of this must be seen for what it is, a mask, a projection of a certain role or idealized self for others to see and believe. These are helpful masks, necessary masks, while making one’s way in the world. But now is the time to acknowledge them and, in the spirit of the Japanese ritual of Discharging Your Loyal Soldier[5], leaders must lay down these masks that were necessary to wear for a time so that they can move into the next season of their lives. And just as the collection of their personas, which forms their celebrated False Self, has carried them into positions of leadership and influence, these same personas now prevent them from embracing their True Self. A recurring manifestation of the False Self regularly shows up for leaders in the days and weeks after receiving a promotion.
The challenge in organizations is that, when high performers are promoted to management, they can struggle to let go of the old work they used to do. And, in an even more pronounced way, when managers move into roles of leadership, they often want to stay ‘connected’ to as many details as possible of the day-to-day running of their section of the organization. The challenge of delegating roles, responsibilities, and daily work to others – and the inability to let go of control and to trust others - is at the root of so much of my work with leaders, teams, and their organizations. Leaders need to learn to examine their personas, to acknowledge the gifts that brought them through their early career, to appreciate the benefits that their ‘being the go-to person for IT’ or being a ‘safe pair of hands in engineering/finance/HR’ has had in bringing them to this point in their careers. And then to begin to ‘discharge’ these personas, to hold them more loosely; to no longer rely on their capabilities as the main elements that define them as leaders. They can always call on the skills, abilities, and experiences that they have learned as they move forward. But they do not have to be defined by them alone. As they ‘transcend and include’ these capabilities, leaders are freed up to dig deeper within their own human experience. They have permission to tap into the deepest aspects of their soul, to be vulnerable yet not weak; to share elements of their lives, their struggles, their questions, and their uncertainties with others. Instead of losing control of their realm of influence, this honesty and self-revelation empowers and inspires others. As, in the words of the Persian poet, Rumi, when they ‘tear off the mask’ of their personas, it gives permission to others to do the same. And it often deepens their influence and connection with others. This ‘death of the ego’, this descent of the Hero and Heroine’s Journey into the frightening depths of deconstruction of who they are, is part of the transition towards the second half of life. But before the work is done, the shadowboxing that Fr. Richard writes about in chapter eleven, must begin.
“Shadow work is humiliating work” he writes. “As you do your inner work, you will begin to know that your self-image is nothing more than just that, and not worth protecting, promoting, or denying.”[6] To do this shadowboxing, requires us to engage in a process of listening to what others see about us that we cannot see in ourselves. And it involves naming the parts of ourselves that we deny – even the great parts, the gifts we have to offer – the parts we are frightened to bring into the open for others to see. This is where a coach comes in, where 360º reviews and certain psychometrics can be helpful to shine a light on areas of our shadow. Having a guide, a mentor, and a mirror that both accepts us and also challenges us with the appropriate level of pressure, at the right time, is a crucial aid for leaders to grow in the midst of their high-pressure working environments.
“We never get to the second half of life without major shadowboxing” writes Fr. Richard. “And I’m to report that it continues until the end of life, the only difference being that you are no longer surprised by your surprises or so totally humiliated by your humiliations!” The first baby steps into the second half of life have taken place. Leaders find that the pain of early-stage shadowboxing is often followed by a new sense of easefulness, born of not needing to always win; not needing to be quite as much ‘in control’ as before. They become increasingly present to themselves and connected to the people and systems around them.
This experience of letting go, dying, and being reborn within the Hero and Heroine’s Journey mimics the pattern of the Paschal Mystery: Jesus Christ departed his ‘ordinary world’ on Good Friday, descended into death, and new life was “done unto” him, as Fr. Richard says of the second half of life, so that he was resurrected[7]. There is a pattern here, the Wisdom Pattern that Fr. Richard refers to elsewhere. But to fully experience this cycle, this Paschal Mystery, this Wisdom Pattern of Departure-Descent-Return, requires leaders to embrace paradox. They must move from “dualistic thinking” to holding the tension of the imperfect.[8] Fr. Richard says that this embracing of paradox has allowed him to become “simultaneously very traditional and very progressive.[9]” His experience of learning this was “sequential, natural, and organic as the circles widened” in his life[10]. Thus, this pattern is not a once-off event but something that is replicated over and over as leaders chart their first few steps into the unknown territory of the second half of life. The dualistic perspectives of the first half of life evolve into non-dualistic perspectives:
· “I can be friendly with my colleagues and have clear boundaries with them around work.
· I can stand behind my actions and know that the board members may not be happy with the decisions I have made.
· I can recommend that we proceed with this merger and accept that I cannot totally control how things will pan out in five years’ time.[11]”
As leaders relinquish control and embrace paradox, they inhabit the ‘widening circles’ of the second half of life. They create the space, the culture, and the conditions for others to grow, and they learn to ‘get out of the way’ just enough to stop being a bottleneck, or a ‘guardian’ of their silo, within their organization. They become, as Fr. Richard writes, elders who “fight things only when you are directly called and equipped to do so.[12]” We can all spot these elders, these truly generative leaders, “sitting in a circle of conversation; they are often defining the center, depth, and circumference of the dialogue just by being there![13]”
When any of us ‘fall upward’ and are led into the second half of life – whether we are a formal leader or not, a public influencer or private influencer in our home or community – we can feel it and others can see it. “Life is much more spacious now, the boundaries of the container having been enlarged by the constant addition of new experiences and relationships…Now you are just here, and here holds more than enough.[14]”
[1] Chapter 1, I don’t have the US book to reference pages
[2] Chapter 1, I don’t have the US book to reference pages
[3] Chapter 1
[4] Chapter 11
[5] Chapter 3
[6] Chapter 11
[7] Introduction, Falling Upward.
8 Chapter 12
[9] Chapter 11
[10] Chapter 11
[11] Boland, Patrick. 2024. The Contemplative Leader. BenBella Books. Introduction.
[12] Chapter 10, Falling Upward.
[13] Chapter 10
[14] Chapter 10
