The Wrong Question

THE UNMAKING, PART 5. The question you've been answering without realizing it.

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What if the question you can’t answer is the only one worth asking?

He came in with a list.

Not a vague sense of things. An actual list. What he needed to do next, in order, with dates attached. He’d clearly spent time on it. He walked me through it the way you’d walk a board through a plan you already know they’ll approve. Competent. Sequenced. Airtight.

I let him finish. Then I asked him a different question. Not what he was going to do. Who he was becoming in the middle of all of it.

The list went quiet.

He started to answer twice and stopped both times. Then he did the thing almost everyone does. He translated.

He took the question I asked and quietly swapped it for one he could actually answer.

“Well, I think the next move is…” and he was back on the list. Back in the plan. Back on solid ground.

I stopped him. “That’s not what I asked.”

He laughed, a little uncomfortable. “I know. I don’t really know how to answer the one you asked.”

Neither do most of us. And it’s worth understanding why.

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Welcome to Leading in the Tension.

I’m Josh. I’ve spent two decades building things and leading people, and I now coach leaders through the part of growth that strategy can’t reach. This is Part 5 of The Unmaking, a six-week series on the truth that transformation isn’t addition. It’s subtraction. Something has to be released before the next version of you can arrive.

Last week I made a promise. I said that once you start believing forward, a harder question shows up. Not what you should do next. Who you’re becoming. This is that week. And I want to sit in why the question is so hard to hold, because the difficulty is not a personal failing. It’s built into how we’re made.

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The Translation

Watch what your mind does with the question. Who am I becoming?

Almost immediately, it converts it into something else. Who am I becoming turns into what should I do next. What kind of person am I forming into turns into what’s the plan. The being question keeps getting translated into a doing question, because the doing question has an answer and the being question doesn’t. Not a clean one. Not one you can put on a list.

This is not a discipline problem. It’s an escape hatch. The translation is how we get out of the discomfort of a question that won’t resolve on command.

And here’s the part that matters. The doing question feels productive. You can spend a whole life answering it. Better strategy, better system, better next move, and the whole time you never touch the question underneath. You stay busy in the top layer because the top layer answers back. The being question just sits there, unanswered, while you produce.

The leader with the list wasn’t avoiding work. He was drowning in work. What he was avoiding was the one question his work was designed to keep him from having to ask.

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Why You Can’t See It

There’s a reason this question is nearly impossible to answer alone, and it isn’t weakness. It’s structure.

The psychologist Robert Kegan spent his career on a single, quietly devastating idea. He said that at any stage of our development, there are things we have and things we are. The things we have, we can look at, hold, examine, decide about. The things we are, we can’t. We don’t see them, because we see through them. They’re not in our field of vision. They’re the eyes.

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Kegan called this the difference between what we hold as object and what we’re subject to.

Whatever you’re subject to runs you from underneath. The belief that your worth is your output. The story that rest has to be earned. The quiet certainty that if you stop producing, you’ll stop being loved. You don’t examine those. You can’t. They’re not thoughts you’re having. They’re the lens the thoughts are happening through.

This is why “just reflect on it” so often fails. You can journal for a decade about who you’re becoming and get nowhere, because the very thing forming you is the thing you can’t see from the inside. You’d need to get behind your own eyes. And you can’t get behind your own eyes.

Thomas Merton, the Trappist monk, named the same problem from the other direction. He said most of us spend our lives building what he called the false self. Not an evil self. A constructed one. A self we assemble out of achievement and reputation and role, and then defend, because it’s the only self we’ve ever known how to be. Merton’s claim, the one that unsettled me the first time I sat with it, is that the true self is not built at all. It’s received. You don’t perform your way into it. You get quiet enough, and honest enough, and accompanied enough to let it be uncovered.

Scripture said it first, and more bluntly. The prophet Jeremiah writes,

“The heart is more deceitful than anything else, and incurable — who can understand it?” (Jeremiah 17:9).

Not that the heart is wicked. That the heart is deceptive, and the first person it deceives is you. You are not a reliable narrator of your own interior. That isn’t cynicism. It’s the same thing Kegan and Merton keep circling from different rooms: the instrument you’d use to assess yourself is the very instrument that’s compromised. But Jeremiah doesn’t leave you there. The next line is God speaking: “I, the LORD, examine the mind, I test the heart” (Jeremiah 17:10). The seeing you cannot do for yourself, Someone outside of you can do. That is the whole hope of the passage. What the heart hides from itself, a witness can find.

Which means becoming is not primarily a construction project. It’s an excavation. And you cannot excavate a site you’re standing on top of.

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The Half-Truth That Traps High Performers

Now, if you’ve been reading this and thinking fine, so I’ll go inward, I’ll do the deep introspective work… I want to complicate that, because there’s a trap on that side too.

Herminia Ibarra, who studies how leaders actually change, argues something that cuts against the grain of most personal development. She says we’ve been sold a lie that self-reflection comes first and action follows. Think your way clear, then act. Ibarra’s research says it runs the other way. She calls it outsight. You don’t think your way into a new identity. You act your way into it. You try on the provisional version, you take the role before you feel like the person, and the acting generates the raw material that reflection then works on. Reflection alone, she found, mostly just deepens the groove of who you already are.

Hold both of these next to each other, because the tension between them is the whole thing.

You can’t introspect your way to a new self. And you can’t see the self that’s forming from inside your own head. So becoming isn’t sequence. It isn’t first figure out who you are, then go do. It’s a loop. You claim the identity before it’s true. You act from it before it’s earned. And then you need something you cannot provide for yourself — you need a way to see what the acting is revealing. Someone outside the lens.

BE then DO then HAVE has never meant sit still until you’re finished becoming. It means stop waiting for the doing to hand you an identity it was never able to give. Claim it, move from it, and get honest help reading who’s actually emerging.

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This is the exact place coaching lives. Not better strategy. Not accountability. The being question, asked out loud by someone who can see the lens you can’t. If something in this is stirring, that’s the conversation I’d welcome. A single powerful conversation: https://lp.novus.global/joshorwick

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What a Witness Actually Does

Here’s what a good coach does, in Kegan’s terms, and it’s more precise than “holds up a mirror.”

A coach takes something you are subject to and makes it an object. Takes the belief running you from underneath and sets it on the table in front of you, where for the first time you can look at it instead of through it. The moment that happens, something shifts that no amount of solo effort could produce. What was invisible becomes a thing you can hold. And what you can hold, you can finally choose to put down.

That’s it. That’s the mechanism. Not advice. Not a framework. A second set of eyes positioned exactly where yours can’t reach.

There’s even a physical version of this. Neuroscientists have mapped two brain networks that work like a seesaw. One fires when you’re locked onto a task, executing, getting things done. The other fires when you rest, reflect, imagine who you might become. They suppress each other. You literally cannot run both at once. Which means the more relentlessly you do, the more you starve the exact capacity you’d need to answer who am I becoming. The busyness isn’t just crowding out the question. It’s shutting down the machinery that could answer it.

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Up Until Now

There’s a default running underneath all of this, and it’s worth saying plainly.

What was will keep being, until you do something different.

A system reproduces itself. The self you’re subject to will keep producing the same life, not because you’re failing, but because that’s what unexamined systems do. They hold their shape. Donella Meadows spent a career naming it: a system’s behavior comes from its structure, and it will keep behaving that way until the structure changes. Left alone, tomorrow is just today wearing a different date.

Which is why the most ordinary phrase I know is also one of the most powerful.

Up until now.

Three words. Watch what they do to a fixed story. “I’m someone who has to control everything” is a life sentence. “Up until now, I’ve been someone who felt he had to control everything” is a pattern with an end date. The first is an identity. The second is a season. The first traps you inside the lens. The second sets the lens on the table where you can finally look at it.

“Up until now” takes what you’re subject to and makes it object. It timestamps the thing you mistook for permanent. It says: that was true, and it does not have to keep being true. Everything I’ve written about becoming lives in the space those three words pry open. Who you’re becoming starts the moment you stop saying “this is just who I am” and start saying “up until now, this is who I’ve been.”

That’s the spark. Not a new plan. A new sentence.

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The Question

So here’s what I’ll leave you holding. Two questions, really, and they belong together.

Who have you been… up until now?

And who are you becoming, the moment you stop mistaking that pattern for a permanent self?

When you feel yourself reaching for the plan, the next move, the list, notice it. That reach is the signal. It’s the exact moment the real question gets swapped for the manageable one. Stay in the real one a little longer than is comfortable. That discomfort isn’t the problem. It’s the first thing that’s moved in a long time.

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Next week closes The Unmaking. The new self doesn’t arrive fully formed. It shows up fumbling, uncertain, learning to walk. And most leaders abandon the becoming right at the threshold, because they mistake the awkwardness of the new for evidence they’ve failed. We’ll sit in the grace of being a beginner again.

This is Part 5 of The Unmaking. If it named something for you, forward it to one leader who’s been answering the wrong question about their own life. If someone forwarded this to you, subscribe here — I write every week for leaders who suspect there’s more available than the version they’ve been performing.