Leading through grief

What I learned from letting it all fall apart

The relentless momentum has stilled.

For many of us, the exciting and wealth-building years of productivity that defined our leadership through the ZIRP era—expansive growth, endless optimization, quarterly targets, and strategic plans that promised control over chaos—has ground to a halt. We find ourselves in an uncomfortable space of liminality, suspended between the growth and certainty we had become accustomed to and the uncertainty of what comes next.

As I reflected on this moment, I came to realize that it contains the same echoes of death, divorce, or any other life-upending context change. While that might sound dramatic, I stand by it. We have lost something that we have become accustomed to, depended on, made decisions around, and allowed to shape the contours of our lives.

And like any difficult moment, the pain of loss can jolt us awake, finding ourselves with one foot in the past and one foot in the future, straddling the inflection point of our becoming. Who did we become in the last decade? Who will we become in the next?

The difference between problems and passages

There are leadership problems, and there are leadership passages.

Problems can be solved. They have clear causes and solutions. They respond to strategy, effort, and optimization.

Passages must be lived through. They ask us to become someone we've never been. They strip away what we thought made us effective and invite us to discover what will make us effective in the future. There is, by definition, loss. Of our identity. Of comfort. Of certainty.

I watched this in my own leadership when I made the decision to leave management consulting for executive coaching. I mourned the security and familiarity of my old life as I faced the daunting task of building a company in an entirely new context.

The leader who emerges from a passage is fundamentally changed—if they're lucky, someone who has learned to live and lead from a different place.

When grief becomes teacher

Earlier this year, my world turned upside down unexpectedly. Grief arrived uninvited, unscheduled, demanding time and space I didn't have and didn’t want to give away. I fought it at first, trying to regain control of my calendar, my productivity, my carefully constructed presence as a leader.

As Francis Weller says, "When our grief cannot be spoken, it falls into the shadow and re-arises as symptoms. So many of us are depressed, anxious, and lonely... moving at a breathless pace, trying to keep up with the machinery of culture."

Eventually, grief had its way. Instead of fighting it, I decided to do something different: I let it wash over me.

Beyond disrupting my schedule, grief interrupted deeply ingrained habits and long-held beliefs. For me, this meant stepping back from the relentless velocity and revenue benchmarks I'd set for myself. In that space, I began asking different questions: not just "what" I was doing, but "why" I had started this company to begin with.

When I returned to that original intention, I realized I was building a company that had drifted from its purpose. I had let unconscious patterns in my operating system (Grow! Control! Optimize!) drive decisions about investments that had nothing to do with my plan. I wasn't in the driver's seat of my own company.

Sociologist Hartmut Rosa writes about our modern compulsion to control and engineer every aspect of our world, noting that "we lose touch with the world when we seek to increasingly control it. The world becomes something hostile — something fixed, something heretofore untamed, and, most importantly, something we need to dominate."

This captures my lifelong struggle: remembering that my role in this world is not to fix, tame, or dominate (particularly challenging as an Enneagram 8). Life periodically offers profound lessons in this reminder. This season of grief was another such lesson.

Grief, too, cannot be dominated. It arrives with its own timing, its own intensity, its own agenda. It refuses our strategic frameworks and laughs at our productivity systems. In Rosa's terms, grief is fundamentally "uncontrollable" and paradoxically, this uncontrollability contains its own wisdom.

What remained beneath all my constructed leadership was something I'd forgotten: a person who could be present with what is, rather than constantly pushing toward what should be. Someone who could find her footing not in strategies that try to containerize everything into neat boxes, but in something deeper—what Rosa calls "resonance," a way of relating to the world through deep presence with what is actually unfolding.

This required a fundamental shift: from attention scattered across endless projects and future bets to simply staying aware of what was happening inside me and around me. The hollow feeling when I opened yet another PowerPoint to conceptualize a way to scale. What I was really hearing when clients discussed with near exhaustion the next step in their career growth: If I'm not constantly achieving, do I have any worth?

In simply watching the world unfold instead of trying to predict what should happen, I received the actual information I needed to move forward. By shifting from performative to receptive presence, I could quiet the "should voices" and listen to what this moment was asking of me.

The lesson ultimately for me wasn't to become a better leader through grief, but to let grief show me what leadership looks like when stripped of everything you think is essential but is actually a distraction. When you can't rely on your usual strategies, you discover what's still there. When your normal patterns stop working, you find different parts of you that are more equipped to navigate new circumstances.

You return to your values. Your purpose. Your soul. You stop listening to the stories that promise control and start listening to what wants to emerge.

What I discovered in my own passage is what I often see reflected in the leaders I work with. Breakdown isn't the opposite of breakthrough. It's the prerequisite.

The invitation hiding in the breakdown

"Silence is a practice of emptying, of letting go," Weller continues. "It is a process of hollowing ourselves out so we can open to what is emerging. Our work is to make ourselves receptive."

This is what I want to offer you: what if your next crisis isn't a problem to solve but an invitation to slow down and receive?

What if the parts of you stuck underneath the current version of you maniacally focused on endless optimization of what already exists have been waiting for this moment of breakdown to finally be heard. And what if it is from those parts that we create what’s next?

But accessing these parts requires us to slow down long enough to hear them. This means shifting from doing to being, from solving to sensing.

A contemplative practice: The inventory of what's no longer working

This kind of work is not about fixing or optimizing. This is about recognition and release.

Sit quietly and ask yourself:

• What leadership patterns that once served me now feel hollow or exhausting?

• What am I trying to control that might be more powerful if I let it go?

• What parts of my leadership identity am I outgrowing?

• What wants to emerge in my leadership that I haven't given permission to yet?

Don't rush to solutions. Let these questions live in you. Let them hollow out space for what wants to come.

The living question

What is trying to die in my leadership so something else can be born?

This isn't metaphorical. In every moment of breakdown, something is asking to be released so something else can emerge. The question is whether we have the courage to let it go, and the patience to discover what wants to take its place.

The invitation is always present. The only question is whether we're willing to receive it.

Keep going,

Stephanie