All business is personal

I’m not a big believer in writer’s block.

Primarily because I’ve never had a time when I sat down to write and drew a complete blank. Or at least a total blank. That’s due in part to the fact that I normally have a few different writing projects going on at the same time. So if one of them isn’t sparking a good writing session, I can just move to another one. Then at some point, usually when I’m least expecting it, that flow will ignite again, and I can come back to those pages.

That’s the usual process. But for some reason, this past week wasn’t yielding that result. I never had a shortage of things to write, but I definitely had a shortage of words to scribe for Cooper North’s story.

That can be frustrating when you know the story is there. It’s almost like you can smell it, but you can’t quite name the scent.

So when I sat down to write this next article for The Possibility Factor here on Substack, I had a bit of a dilemma.

I want to be transparent about that because this publication exists to give you a behind-the-scenes look at the book as it’s being written — and this week, it wasn’t.

I’m not sure if life got in the way or the story itself was just having a moment of rebellion. And that’s created a strange little test of the very thing I write about here: what happens when the work that usually keeps you anchored stalls, and you feel the pull to drift someplace easier instead.

I’m not going to drift. But I am going to be honest about where I actually am, because I think that’s more useful to you than pretending I’m somewhere else.

Where I am is this: I know the next scene I have to write. I haven’t written it yet. But I already know what it says, and it won’t leave me alone — so this week, that’s what we’re going to sit with together.

In our last time together here, I told you how characters have a way of showing up uninvited and rearranging the whole story.

Michael Harper, founder of Kestrel Point Capital, was one of those characters — an angel investor who reached out just as Cooper’s business was feeling the pinch of diminishing revenue and rising costs.

The scene I’d originally planned had Cooper walking into Kestrel Point’s conference room, pitching their senior team, and walking back out again.

That’s not what’s happening anymore.

Here’s what I know about the new scene before I’ve fully written it: Harper doesn’t have Cooper meet with his team. Instead, he meets with Cooper himself. Not something he would ordinarily do, but he senses something about Cooper and wants to get his own read on him.

He’s read Cooper’s numbers, his history, his trajectory — and he’s not ready to make an offer so much as to make an observation. He believes in Cooper. He also believes Cooper isn’t ready for what real growth capital would demand of him. Not because Cooper isn’t good enough. Because he hasn’t yet done the internal work that would let him survive being handed more.

So instead of a rejection, Cooper gets a redirection. And the first thing Harper hands him isn’t a term sheet. It’s a lesson.

I’ll let you sit in the room with them the way I have been.

Imagine Cooper talking about margins, clients, market shifts, and competitive pressures.

Harper listens politely.

Then quietly says, “Cooper... all business is personal.”

Cooper almost laughs. “With respect, Michael, it really isn’t.”

Harper smiles. “No?”

“...”

“Then why are you taking this meeting so personally?”

“You built this company.”

“You shaped its culture.”

“You hired every one of those people.”

“You’ve attached your identity to its future.”

“So tell me again... how is this not personal?”

Cooper doesn’t have an answer.

Neither do I yet, fully — not one I could write down in a way that would satisfy you today.

And neither, probably, do you, if you’re honest about your own business the way Harper is asking Cooper to be about his.

We talk about business in the language of strategy because strategy feels like something we can control. Margins can be improved. Markets can be studied. Competitors can be outmaneuvered. It’s all very manageable, on paper.

But underneath almost every business decision I’ve ever watched someone agonize over — including my own — is something that has nothing to do with strategy at all. It’s about identity. It’s who I am if this doesn’t work, or if I have to change it. We dress that question up in spreadsheets because the spreadsheet version feels survivable and the identity version doesn’t.

Harper isn’t offering Cooper money. He’s offering him a mirror. And the uncomfortable gift in it is that Cooper can’t take the capital without first being willing to look.

I still don’t know exactly how Cooper answers Harper in that room — that’s the scene I still have to write. But I know what it makes possible for the rest of the book: a mentor who doesn’t rescue Cooper and doesn’t reject him either. One who sends him out to do the harder thing first.

That’s rarer, in fiction and in life, than a clean yes or a clean no.

I’ll be back soon — hopefully with the scene itself, not just the notes for it. Until then, here are some questions to sit with.

• Where in your business are you speaking the language of strategy about something that’s actually about identity?

• If someone who believed in you told you “you’re not ready for this yet” — not as a rejection, but as an honest read — what do you suspect they’d say you weren’t ready for?

• Looking back, is there a decision you once treated as purely financial that you’d now admit was never really about the money at all?

If you’re new to The Possibility Factor, this publication offers a behind-the-scenes look each week at the book I’m currently writing under the same title. Our central character is Cooper North, a business owner learning that much of what he thought he knew isn’t giving him the answers he needs.

Why does this matter to us beyond the pages of this book? Because most of us are, in our own way, sitting across from our own Michael Harper — even if he hasn’t shown up yet.

Note: You can find the earlier chapters and reflections collected here: The Possibility Factor.