Advisory Notes: Money Lacks Logic

What's actually driving your team's financial behavior.

Here is something I’ve never heard a creative firm leader say out loud, even though most of them know it’s true:

The way your team behaves around money has almost nothing to do with money.

Not the reluctance to ask for what the work is worth. Not the freeze before a difficult conversation about a budget. Not the resentment that builds quietly when someone feels undervalued and can’t say so directly. None of that is rational. None of it was formed by logic. It was formed long before logic was available — in childhood, in households where money meant something beyond its face value. Where it meant safety, or power, or love, or the threat of its withdrawal.

You inherited your relationship with money before you could read.

So did every person on your team.

* * *

This isn’t a metaphor. It’s developmental fact.

We absorb the emotional meaning of money — and of authority — before language arrives to help us categorize what we’re learning. A child doesn’t decide that asking for things is dangerous, or that needing too much will cost them something. They feel it. They read the room. They adjust. And those adjustments become the operating system that runs beneath every adult financial decision they will ever make.

The child who learned that money was scarce and that asking created tension becomes the designer who undercharges and resents it. The child who learned that approval was conditional becomes the creative director who can’t hold firm on a fee without feeling like the relationship is at risk. The child who was never allowed to want too much becomes the writer who doesn’t negotiate, doesn’t push back, and privately wonders why they’re always a little underpaid.

They are not being irrational. They are being exactly as rational as their earliest education taught them to be. The problem is that education was designed for a different environment — one where the stakes were belonging, safety, love — not a client negotiation in 2026.

* * *

I know this from the inside.

My own relationship with money was shaped before I was placed with the family that adopted me. There was a contract — a literal one, with Children’s Home Society — that established the terms of my belonging. My father kept ledgers. Every penny tracked. My expenses, itemized. I learned early that I had a cost, and that costs have thresholds. I spent decades not asking for what I was worth, not because I didn’t know my value, but because asking felt like the thing that might end everything.

That’s not a money problem. That’s an attachment problem wearing a money problem’s clothes.

And when I finally understood that — really understood it, not just as an insight but as a felt truth — my relationship with money began to change. Not instantly. Not completely. But the behavior stopped running me from underneath.

* * *

As a leader, this is your problem too.

Not because you caused your team’s childhood. You didn’t. But because you are now the authority in the room. And authority, like money, is never neutral. It lands on people according to what they learned authority meant before they were old enough to question it.

The person who goes quiet in your presence isn’t being passive. They may be doing exactly what kept them safe at eight years old. The person who bristles at any direction isn’t being difficult. They may have learned that compliance cost them something they couldn’t afford to lose. The person who never asks for a raise isn’t lacking confidence. They may be carrying a ledger that was never theirs to carry.

You cannot fix any of this for them. That’s not your role and it’s not your right.

But you can stop misreading it. You can stop labeling the freeze as laziness, the bristle as ego, the silence as indifference. You can create enough safety in the room that the old operating system has less reason to fire.

That’s not therapy. That’s leadership.

* * *

Lana, my therapist, once told me I was extremely resilient.

I said: “So trauma is a good thing? I learned how to cope.”

She said: “You were lucky the damage wasn’t worse. It could have killed you. Lots of people are not so lucky.”

I’ve thought about that for years. The people on your team who didn’t get lucky — who are still running the old system at full volume, in every meeting, every negotiation, every performance review — they are not broken. They are doing what they learned.

Understanding that changes how you lead.

Not with pity. With accuracy.

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Ted Leonhardt is a creative advisor based in Bellingham, Washington. He works one-on-one with founders and leaders of independent creative firms. Advisory Notes is one of two series on his Substack — the other is Becoming, a memoir in essays.