The Shadow Nobody Wants to Lead With

The Shadow Nobody Wants to Lead With

I was dragging for years and calling it leadership.

We spent eight months preparing before Varment Guard opened its doors. Permits, trucks, equipment, the thousand small decisions nobody tells you about. And at some point in there I had four words put above the door where every person who worked for us would walk under them.

Failure is not an option.

I believed it. I still believe some of it. That sentence built a company that eventually employed hundreds of people, and I am not going to stand here at seventy-four and pretend it was a mistake. It worked.

But I have been thinking lately about what a sentence like that cannot admit, and about who pays for the part it leaves out.

What the shadow actually is

Richard Rohr has a line that has been following me around for a couple of years now: what we do not transform, we will transmit. He is talking about pain, mostly. But I have come to think it is just as true of the parts of ourselves we have never looked at directly — and that a leader transmits those at a volume nobody else in the building can match.

That is what the shadow is. Not the evil in us. The denied part. The material we have decided is not us, which goes on operating anyway, from underneath, with all the force of something that has never been questioned.

And here is the thing about shadow in leadership specifically. It does not usually show up as the obvious vice. It shows up disguised as your greatest strength, running past the point where the strength was useful.

Drive becomes a refusal to let anyone move at their own pace.

Decisiveness becomes an allergy to being slowed down by someone else’s thinking.

Protectiveness — and this one is mine — becomes the conviction that you are the only one who can carry it, which is not actually protection. It is a failure to trust the people you hired.

The ceiling I painted

Failure is not an option is a fine thing to say when you are eight months from opening and everything is uncertain. It is a different thing entirely when it becomes the air a hundred people breathe. Because what the people underneath that sentence hear is not courage. What they hear is: there is no room here to be struggling. No room to say the route is wrong, the schedule is impossible, I am in over my head, my marriage is coming apart and I cannot give you another sixty-hour week.

I thought I had painted a standard above that door. I had also painted a ceiling.

There are relationships from those years that are painful for me to think about now.

My drive was not fair to the people in the room. I harmed them. I am not going to dress that up or soften it into a lesson. I was not a monster — I was something more ordinary and more common, which is a man who mistook his own urgency for the right thing, and who ran people over while believing he was carrying them.

Most of them have gone on to successful lives in spite of me. That is the phrase that costs me. Not because of the hard training I thought I was giving them. In spite of me.

A few are still bitter. I understand why.

You cannot drag people

What I learned, far later than I should have, is the thing Jim Collins spent a book establishing: you cannot drag people along by sheer force of will. Collins went looking for what turned good companies into great ones and found that the leaders who did it were not the force-of-will personalities. They paired ferocious professional resolve with genuine personal humility — Level 5, he called it — and the magnetic, driving celebrity CEO turned up mostly in the comparison companies, the ones that did not make the leap. He put the sequence plainly too: first who, then what. The right people do not need to be dragged.

And if you are dragging, that is information about you. Not about them.

I was dragging for years and calling it leadership.

Why I keep teaching the Enneagram

This is where the Enneagram earns its keep for me, and why I keep teaching it to people who come in thinking it is a personality quiz.

The Enneagram is not fundamentally a description of how you behave. It is a description of what you are defending against, and the strategy you built so young that it stopped feeling like a strategy. Each type has a passion — the old tradition called them deadly sins, which overstates it — and the passion is precisely the engine that runs in the dark. For the Eight it is intensity, excess, too-muchness: the conviction that more force is always the answer, because force is what kept me safe once.

Nobody wakes up and decides to lead from their passion. That is the point. It is operating before you are awake.

And the instincts underneath — whether you are organized around self-preservation, around the social field, around the intensity of one-to-one connection — determine where that passion shows up first and most destructively. A self-preservation Eight hoards control over resources. A social Eight makes everything a question of loyalty to the group. These are not abstractions. They are Tuesday afternoon, in a meeting, in the thing you said that landed harder than you intended.

What the Enneagram gives a leader is not insight. Insight is cheap and most of us have plenty. It gives you a place to look before the damage, and a vocabulary for the thing you are about to do again.

Management with a title on it

Which brings me to what I actually want to say.

There is a kind of leadership that is competent, organized, well-reviewed, and entirely unexamined. The budgets balance. The people stay, mostly. The metrics are fine. And underneath it the leader is transmitting something they have never looked at — a fear, a hunger, an old wound in a good suit — and everyone in the organization is arranging themselves around it without ever being able to name what they are arranging themselves around.

That is not leadership. That is management with a title on it.

The difference is not charisma or vision or any of the words we put on the job posting. The difference is whether a person has done the work of meeting the part of themselves they would rather not meet, and keeps doing it, because it does not stay done.

Rohr’s point about transmission is the whole case for shadow work in a practical, unsentimental, bottom-line sense. You are going to transmit something. That is not optional. The only question on the table is whether you have looked at what you are sending.

The Strength That Went To Far Reflection Sheet

The door

I think about that door a lot now.

If I were painting it today, I would not take the words down. They were true about the work. We were building something that genuinely could not afford to fail, and saying so out loud was honest.

But I would want the people walking under it to know the rest of the sentence — the part I was not able to say then, because I had not met it yet. That failure was not an option for the company, and that this was never the same thing as there being no room to be human underneath it. That I was more afraid than I let anyone see. That the force I was leading with came from somewhere, and I had not yet asked where.

I would want to have known, standing there with the paint still wet, that what would cost us most was never going to be a bad quarter.

It was going to be the part of me I had decided was not worth examining, operating at full strength, for twenty years, over the heads of everyone walking through that door.

Peace and every good.

About Jim & Lynette Vaive

Jim and Lynette Vaive are the co-founders of spirit of EQ and co-authors of The Mystical Seeker. They are Master Certified Coaches, certified Narrative Enneagram teachers, and Certified Spiritual Directors. Together they hold credentials in Spiritual Emotional Intelligence (SEQ) — a framework rooted in Lynette’s Doctor of Ministry research — and serve individuals, small groups, and organizations across faith traditions. Learn more at spiritofeq.com.

Sources

Richard Rohr on the shadow and on transformation — a recurring theme across his work, developed at length in Immortal Diamond (2013) and Falling Upward (2011).

Jim Collins, Good to Great (2001) — Level 5 Leadership and “first who, then what.”