When The Math Doesn't Matter
Today I’m sharing a story from a recent coaching session — not just because it was powerful, but because it illustrates two truths worth sitting with:
Money isn’t everything.
It might be the medium of my coaching, but it’s rarely the point. What matters is how money can empower a richer, more meaningful life. The primary goal isn’t “more money” — it’s more meaning.
Big changes require bravery.
...the kind of bravery we don’t always recognize in the moment. This story is about what it looks like to reach a turning point — and why it’s worth rehearsing these moments before they arrive in your own life.
With that, let's dive in.
A few weeks ago, Samantha sat across from me on Zoom, eyes watery, voice shaking.
“I think I’m going to quit,” she said. “I just can’t keep going like this.”
She’s a financial forecaster for a large corporation — a thoughtful truth-teller in a system that, right now, doesn’t seem to value the truth she's sharing.
Leadership pushes inflated targets. Sales teams pad the numbers. Samantha presents the honest forecast… and gets labeled the problem.
The politics are exhausting. The pressure is relentless. And after nearly 20 years, she’s not just tired — she’s starting to unravel.
But here’s the key part:
Samantha has done the work.
She has:
A massive emergency fund
A paid-off car and no consumer debt
Robust retirement accounts
Ample cash in the bank
So when she said she was thinking about leaving, I paused. Then said this:
“Samantha, please don't let this decision be about the money.”
Despite knowing her own balances, hearing me say the words was the permission she needed to put herself first. To prioritize her happiness and wellbeing over making "the responsible decision".
Because for the first time, she saw it clearly:
She’s not trapped.
She’s not reckless.
She’s ready... if she can be brave enough to take the step.
And what comes next is not about optimizing.
It’s about healing, and designing a life to be excited to live.
I suggested writing a resignation letter and leaving it — sealed, for now — on her desk.
Just a symbol. A reminder of her agency.
Then I gave her a second assignment:
“Write down what a great day looks like. A great week. A great month.
Not what you’re running from...
What you’re running toward.”
She sat in pensive silence. She seemed disappointed and a little empty. After years of prioritizing others and putting one foot in front of the other, she didn’t know what to write.
So that’s the work now.
And she’s ready.
Quick Insight:
With a little luck, there comes a point in every financial journey where the numbers no longer hold you back — they hold you up...they support your best life.
If you’re at that junction: be brave.
If you’re not there yet: be inspired. Because every debt you pay down, every dollar you invest, every growth system you build — it’s all building to a moment like this.
The moment where money stops being the obstacle… And starts being the reason you get to choose.
Money Question:
If money didn’t have to be part of the decision…
What would you choose next?
Take this question wherever your mind wants to go.
If this newsletter strikes a chord, schedule your Clarity Session to explore what coaching might look like for you.
In your corner,
— Andrew
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