The Identity Tax
MONTHLY NEWSLETTER | June 2026
For years, I said yes to opportunities I knew weren’t right for me.
Not because I didn’t know better. I did. The signals were there — quiet at first, then increasingly insistent. Something was calling me toward a different way of leading, a different way of living. And I kept looking away.
Fear has a way of making the familiar feel safe, and sometimes even wise.
Maybe it shows up as a low-grade restlessness you can’t quite name. A sense that the work that once energized you has become a responsibility you manage rather than a calling you love. You’re genuinely successful. But a voice keeps asking: “Is this it?”
Most leaders don’t talk about this. Not openly. Instead, restlessness gets managed. Reframed as stress. Scheduled for after the next milestone. Rationalized into something smaller and more containable.
And for a while, that works. You convince yourself you’ve handled it.
Then it comes back. Not louder, exactly, but harder to dismiss. It doesn’t demand. It simply waits — showing up in the stillness between meetings, in the pause before you answer, “How are you?” Lingering in the moment you catch yourself wondering whether this is still the life you actually chose.
THE PATH THAT BUILT YOU
“More is better” isn’t a philosophy most leaders consciously adopt. It arrives gradually, reinforced by every promotion, every expanded mandate, every moment the organization signals that your value is measured in output, scope, and upward trajectory.
And for a long time, it works beautifully.
The identity that forms around it is not superficial. It is built from real capability, real sacrifice, real achievement. You earned it. The expertise, the decisiveness, the ability to walk into a room and know what needs to happen — these are genuine strengths, and they served you and the people around you well.
But somewhere along the way, the path that built you begins to define you. And that is a different thing entirely.
I know this territory — not only from the leaders I work with, but from my own years of staying on a path I had outgrown.
When your sense of worth becomes inseparable from your role, your title, your output — the question “Who am I if I step off this path?” stops being philosophical. It becomes threatening. The lifestyle, the identity, the quiet but ever-present awareness of what people will think — these are not shallow concerns. They are the architecture of a life carefully constructed over decades.
Leaving it doesn’t feel like growth. It feels like disappearing.
The greatest risk isn't losing the path that built you — it's mistaking it for the only path you'll ever have.
WHAT AI IS ACTUALLY EXPOSING
Lately, something else changed. Not because the restlessness is new — it has been there for years, waiting. But the world around you is no longer willing to wait with it.
AI is making that feeling harder to outrun.
Here is the connection: the restlessness you’ve been managing is not separate from the leadership challenge AI is placing in front of you. They are the same invitation, arriving from two directions.
For decades, the dominant leadership model has rewarded a particular set of qualities: the ability to know, to decide, to control, to deliver. Leaders were valued — and they valued themselves — in proportion to their expertise, their certainty, and their capacity to drive results through sheer force of will and positional authority.
It wasn’t the only way to lead. But it was the most rewarded.
AI is not simply automating tasks. It is exposing the limits of that old leadership model with a speed and permanence that organizational culture pressure alone never managed. The pandemic cracked the door open briefly — leaders led more humanly, more vulnerably, more honestly — and then the old system reasserted itself. The armor clamped back into place.
AI is not offering that retreat.
What it is revealing, just beyond the productivity conversation, is a leadership identity crisis that has been forming for years. If your value as a leader is anchored in being the smartest person in the room, the most decisive, the one with the answers — that anchor is dragging you down.
This is not a skills problem. You cannot train your way out of an identity that no longer fits.
What is being asked of leaders now — genuine curiosity, psychological safety, the ability to hold uncertainty without collapsing it prematurely — is not a set of competencies to be acquired. They are qualities that emerge when a leader stops performing and starts leading from the inside out.
That is the real disruption. And it has been waiting for you.
THE SIGNAL YOU MIGHT BE MISREADING
Here is what I have witnessed, again and again, in leaders who reach this moment.
You experience a shift. Small at first, barely noticeable beneath the noise of uncertainty and everything at stake. But unmistakable once you know what to look for.
Alongside the fear, there is excitement.
In her book Playing Big, Tara Mohr draws on a teaching from Rabbi Alan Lew that I find indispensable. The Hebrew Bible uses two distinct words for fear. Pachad is projected, imagined fear — the catastrophizing voice that conjures worst-case scenarios and whispers that everything could fall apart. It is the fear high achievers know intimately.
The second is yirah. It describes the feeling that arises when we find ourselves inhabiting a larger space than we are used to. When we are standing, as Lew puts it, on holy ground.
The two can feel remarkably similar in the body. Which is why so many leaders misread the signal entirely — filing the excitement under risk, under irresponsibility, under not yet.
Pachad contracts. Yirah expands, even when it frightens.
When that particular combination arrives — the unease and the aliveness together — it is not a warning to retreat. It is one of the most reliable signals that a truer path forward is becoming possible.
THE HOMECOMING
Some people frame what’s ahead as reinvention: a new leadership model to adopt, new competencies to build, a better version of yourself to construct.
I see it differently.
What I have witnessed in leaders who move through this threshold — and in my own life — is that what waits on the other side is not reinvention. It is a return to the self that existed before the armor, before the performance, before “more is better” became the only available path forward.
There is often a moment in coaching when a leader catches a glimpse of this. It arrives in a quiet moment, sometimes in the middle of an entirely different conversation. You remember who you were before the climb began. A quality you had set aside because it didn’t fit the model — curiosity, playfulness, the willingness to not know. Something that felt, for a moment, like being a child again.
Not naïve. Not unformed. But free in a way that the constructed identity never quite managed.
This is not regression. It is retrieval.
I know this feeling from my own experience of finding that box. Opening it didn’t just bring back memories. It brought a clarity I didn’t know I had been missing — a recognition so immediate and so certain that I found myself wondering how I had ever set any of it aside.
The restlessness and the retrieval, it turns out, were always the same thing. Pointing in the same direction. Waiting for me to be ready to look.
Which means this moment — uncomfortable and uncertain as it is — is not a crisis to survive. It is an invitation to come home to yourself. And to lead, finally, from that place.
That is what becomes possible on the other side of the identity tax.
What waits on the other side isn't a new version of you — it's the part of you that was there before the armor.
THE GOOD NEWS
I know that good may be the last thing this feels like right now.
The disruption is real. The uncertainty is real. The cost of carrying an identity that no longer fits — that is real too. I am not asking you to reframe difficulty as opportunity in the way that leadership content so often does, with a kind of relentless positivity that leaves you feeling more alone than before you started reading.
What I am saying is something different.
The fact that you feel the gap — between the success and the aliveness, between the path you are on and the one that keeps calling — is not a problem to solve. It is a signal to follow.
And the leaders I most admire, including so many I have had the privilege of working alongside, have found that following it leads somewhere worth going. Not to a perfect version of themselves. Not to a life without complexity or pressure or hard decisions. But to a way of leading that is sustainable, because it is sourced from the inside rather than performed for the outside.
This way of being doesn’t cost you yourself. You don’t have to have it figured out. You don’t have to be ready. You simply have to be willing to stay with the yirah long enough to let it show you what it’s pointing at.
That flickering sense of excitement beneath the fear? It knows the way.
And you don’t have to find it alone.
If this has landed close to home, I would be honored to explore it with you. This is the terrain coaching was made for — not because it offers a roadmap, but because having a steady thinking partner sit in the uncertainty with you changes what’s possible.
References:
Lew, A. (2005). Be still and get going: A Jewish meditation practice for real life. Little, Brown and Company.
Mohr, T. (2014). Playing big: Practical wisdom for women who want to speak up, create, and lead. Avery/Penguin.
