Leading through rebirth

The skills the coming era demands aren’t taught. They’re earned.

How are we going to build a brave new world? Who is going to lead us there?

There are many names for the era we are living through — from systemic terms like Joanna Macy’s The Great Unraveling to mythological terms like Francis Weller’s The Long Dark.

Call it what you like, we are living through a rebirth. I find this equal parts thrilling and terrifying. When I come home to myself, I have the conviction that each of us is on earth at this time for a reason. Not just those with titles or platforms — all of us.

Whether you identify as a leader or not, you are responsible for leading your life. And leading your life is where leading through rebirth begins.

It is where you have gained the most critical leadership skills. Not in a corporate training room, with a fancy coach, or in a business book.

Yet, no one acknowledges these hard-won skills, much less cultivates them.

We draw a false line between leadership development as a professional activity and the rest of life — where we experience the real lessons of navigating loss, showing up through difficulty, and emerging on the other side.

The good news is that you likely have many of the necessary skills — you just may not recognize them in yourself. I know I didn’t.

When I started to listen to Stories of Transformation, I wasn’t connecting the dots between threshold crossings and The Long Dark. But the relationship is too obvious not to call out, especially at this moment.

We are at the beginning of an era defined by loss, grief, uncertainty, and disruption — and therefore by beginner’s mind, possibility, and the urgent need to build something new. The leaders this era demands are not those who can execute against a clear plan. They are those who can move through the unknown — and bring others with them.

If formal leadership development was the preparation for the optimization era, Threshold Work is the preparation for the era we are entering now.

I am 57 Stories of Transformation into my listening project, and what I am witnessing grows clearer with every story: the most important leadership skills cannot be trained. You earn them through crossing a threshold into the unknown.

These skills follow the arc of the Universal Map for Transformation — The Skills of Departure, The Skills of The Unknown, and The Skills of Emergence. The people living these skills are the leaders we need now. And if you have crossed a threshold, you may already be more prepared than you know.

The first threshold crossing is always the one you didn’t choose. And the first skill it demands is the one we’re least prepared for: knowing how to leave.

The Skills of Departure
Even something as common as a colleague leaving can be experienced like a death. And yet in most organizations, there is no model for honoring the loss. There are no rituals, no permission to grieve, no acknowledgment that something real has ended.

More significant professional and organizational losses are even less likely to be honored: the target you didn’t hit, the scandal that was exposed, the funding that was taken away, or the humans replaced by machines.

Every loss has its cost. The more the loss is minimized, the higher the cost.

Threshold crossers have an instinctual ability to honor the loss and let it move through them, and others.

B reflected on their experience leaving a leadership role and decade-long tenure at their firm: “It felt like we were never going to see each other again. And if it’s the last time we’re going to talk, we need to say something of importance.”

A colleague’s departure shakes people because it brings their own choices into focus. They can leave, or they can turn the work into something that brings them alive. Like facing your own mortality, both options are scary. Both are enlivening. A leader who can name the ending, rather than letting it pass unacknowledged, creates the conditions for something true to emerge in its place.

What makes this skill possible in a professional context is almost always cultivated somewhere more personal first. Emilie shared an exchange she had after losing her mom to Lewy Body dementia: “I’ve been thinking lately, what can be the gift of my death? A goal would be for me to live and die in such a way that my death becomes a source of growth for others.”

The person leaving is often the one most equipped to create meaning through the ending. B did this by methodically documenting their work — not just as a handoff, but as a way of seeing whether what they had built could stand on its own. Priscilla turned her last trip to headquarters into what she called a living funeral — a deliberate farewell that brought to the forefront “what life should really be about.”

Each loss carries the same invitation — to honor what was before moving into what could be. A leader’s ability to hold the ending, and all of its beauty, is what makes the next beginning possible.

Then comes the part with no map.

Waves of Grief is a beautiful community practice for honoring loss, and letting it move through you. Thank you, Candice, for sharing this resource.

The Skills of The Unknown
If The Departure feels like a death, The Unknown feels like a freefall. Paul described his sudden heart attack and the resulting loss of his high-status persona as being “dragged screaming into a new reality without any sense of what was going to happen.” Consciously or not, most leaders are doing everything they can to avoid this — showing up, as Natalia described, “measuring up to what an executive is, trying to be what I thought everyone needed from me.” This understanding of leadership leaves little room for The Skills of The Unknown.

I didn’t realize I was avoiding anything, I was so wrapped up in being all things to all people: from office mom to occasional therapist, P&L owner to creative fuel. That felt like who I was. Until I was forced into the territory of the unknown.

Whether force is necessary is the tricky part. As Emilie astutely questioned: “Would one ever willingly put themselves in enough of an unknown situation to trigger the truly transformative experience?” What I have learned from my experience, and from my storytellers, is that once you’ve lived through the unknown, you learn not only that you can survive, but also that you likely underestimated how many skills you have for navigating it.

The skills the unknown demands fall into three practices: coming home to yourself, stepping outside your story, and staying in the dark long enough to emerge changed.

Natalia described the time before her descent as “ruminating 24 hours a day, all I could do was stay vigilant.” While her partner had tried to break her out of this reality, it was her daughter’s tears and an innocent question — Why are you like this? — that cracked it open. After an initial period of doubt and self-questioning, she arrived at the essential question: “Where is the person I have known all these years, and is she going to come back?” Coming home to yourself begins with knowing you’ve left.

Ashley experienced her own shift after a move from New York to London, thrust into full-time parenting while she found childcare and learned a new market. From that unknown place, she was able to see the “stark difference between what I thought was a good balance and what was actually frenzied and unhappy.” She joked that it “shouldn’t take moving across an ocean to design your life” — but it does often take a pattern disruptor to step outside the story you’ve been living inside.

Stepping outside your story can happen relatively quickly. Staying there is harder. Priscilla, an experienced threshold crosser, named her biggest fear as “converging too soon, trading corporate life for corporate life” — and it is exactly that fear, held honestly, that becomes the skill. Trained as an engineer, she developed a practice: ask What if...? and collect data until a possible future begins to take shape. The question moves, eventually, from whether something will happen to when and how.

A leader’s ability to move through the unknown with a steady presence is what will separate chaos from emergence.

And then, sometimes without noticing, the ground begins to return.

Victoria Song distills The Skills of The Unknown so beautifully, and lands them in the body. Thank you, Exposure Therapy, for this resource.

The Skills of Emergence
Emergence is what we most want from our leaders — it’s the stage we want to skip to, as if it arrived out of thin air. Sometimes it feels like it does. This was my experience, returning to a leadership role after maternity leave. My departure and journey through the unknown were invisible to everyone around me; after six months, they received a neatly transformed package. One they didn’t fully recognize, but were happy to benefit from. Who doesn’t love a transformed leader, fully in their power?

That power emerges as the spark of the creative self — the self who has been there all along, underneath all the layers of a borrowed life. Monicka put a fine point on this, after discovering the thread that connects her work: “Your most authentic identity is your most creative identity.”

The creative self knows it is not enough to move away from something. We need something to move toward — for ourselves, and those around us. I have yet to hear a story, my own included, where the storyteller didn’t have an inkling of what they wanted to create in the world.

The Skills of Emergence are the skills of allowing that inkling to come forward and take shape: dreaming your way to what’s next, and experimenting your way there, often in parallel.

Pre-threshold, possibility is hard to access. People are depleted, “moving through honey” as Nili put it, unaware of what might exist on the other side. After crossing, the possibilities can feel almost overwhelming — once the creative, dreaming self is nurtured. This nurturing can be smaller than you think.

Nili recognized this in her current experience of transformation: “I’ve been building this realization that I need to dream. My commitment to myself this week was to look for inspiration, to use my watercolors to start drawing a future: Is it a house? Is it a social life?” This dreaming practice sets the financial and professional considerations aside, and allows the heart to lead.

After leaving her executive role, Natalia asked herself: What next? She had no idea. “So I decided: I’m going to experiment with the things that I find interesting and I will connect the dots later.” This led her to art classes, a coaching certification, and writing a play. Each practice provided distance from her former reality — and more importantly, the perspective to “get out of the bottle and read the label,” to see how much more expansive her reality had become.

A leader’s ability to dream their way to what’s next — and experiment their way there — is not what we train for. It is what we do to remember we’re alive. And in the era ahead, it is what we owe each other.

Natalia is building, “a psychotechnology for leaders navigating with an outdated GPS. A system of artifacts, spaces, and questions designed to make the map visible before it’s too late to update it.” She uses collage to make her own map visible.

---

I have learned a great deal about leadership on the job, and through formal development. That learning has merit. But in the coming era, the necessary competencies look different. The skills of leading through rebirth are earned in the most personal corners of a life — and we can no longer afford to leave them unnamed.

Mimo gave me a model for where to begin. As she approaches her 40th birthday, she is writing 40 Lessons that honor the various forms of Mimo: the immigrant, the student, the founder, the parent.

What are your leadership lessons? Where did they come from? And which ones will serve you and us as we lead into a brave new world?

I’d love to hear them.

---

Thank you to all of the people who have shared their stories (and their tears) with me. You can sign up to share your story here.