Here's an Unusual Way to Strengthen Your Self-Trust - With Money
You may have heard me say this before — and it’s not hyperbolic, either: When someone buys from me (regardless of the dollar amount), I want them to feel like it is the best damn money they’ve ever spent!
Seriously.
I never want them to question their decision.
Because if they do, it doesn’t just affect our relationship — it impacts the one they have with themselves, too. Especially when it comes to trusting their own decisions.
How can I say this so assuredly? First-hand experience.
I don’t know about you, but the trigger for me questioning if I spent my money on the “right” thing is often centered around the answer to this question:
Did I get what I was expecting — based on what I was promised?
If the answer is a resounding: Yes! My experience affirms my choice.
If the answer is a resounding: No! Ooof…it’s down the rabbit hole I go — along with my sense of self-trust.
I start to wonder:
What did I miss?
Where and how did my research and vetting process fail me?
And, I become extremely cautious.
I start taking longer than usual — sometimes spending more time than necessary second-guessing subsequent decisions.
That’s because when your self-trust takes a hit, it doesn’t just affect that one decision — it lingers.
You become more hesitant.
You might second-guess future investments.
You might even shrink your vision or delay important moves — all in the name of “being cautious,” when really, you’re just trying to protect yourself from the disappointment of making a choice that didn’t pan out as you hoped or expected or had been promised.
That’s certainly been true for me, and it might be exactly what’s behind the silence from someone you’re waiting on to say, “yes.”
In my work, I never guarantee a specific outcome. Not only does doing so veer into legal territory, it’s pretty obnoxious to assume that level of control.
However…I strongly believe in having a process for making decisions.
This way, whether you get the outcome you want or not, you have a process you can reference and tweak, as required.
A Little Behind-the-scenes
As you may know from first-hand experience with doing the Financial Flywheel™ — it's a simple, yet profound tool designed to help you (re)discover what it is you want money to do for you.
For some people, even the idea of asking, “what do I want money to do for me?” is foreign. It’s like wow…I have permission to do that?!
Yet, it’s how I’m able to grab their attention to help them shift to engaging with their money by design — rather than by default.
I originally created the Financial Flywheel™ (previously called Financial Wheel) over twenty-years ago. I’ve had people tell me they’ve found doing the exercise hard because it asks them to suspend their current reality for a moment. (Truth is: even their resistance is filled with insight!) But I’ve yet to have someone tell me that they didn’t find some aspect of it eye-opening.
Here’s why I love guiding people through the exercise — whether one-on-one or through the lead magnet: That simple circle with four quadrants? It reveals a lot of information and insight, including:
Your strategy - Is it solid or on shaky ground?
What’s causing your financial stress - Is it acute or ongoing? And is the culprit what you thought it was?
The choices you’re making…or avoiding…or not even seeing as possible — and how those choices shape your self-trust.
The strength of your systems - Are they supporting your strategy, or is your approach haphazard?
None of what I’ve just noted is separate from your mindset or your outcomes. In fact, they are interwoven.
That’s why I believe strategy, self-trust, and systems must work together.
Strategy gives you direction.
Systems give you support.
But self-trust? That’s the glue, baby — it holds everything together!
Without it, even the best-laid plans or beautifully color-coded spreadsheets can feel shaky.
And that’s where mindset shows up — not in vague affirmations, but in your willingness to make decisions, take risks, and course-correct without spiraling.
The Unexpected Power of Mid-Year Reviews
In doing my mid-year review, I found myself questioning a choice I made earlier this year. One of the things I’ve learned to do when this happens is to ask myself whether I’d question the choice if the outcome was what I wanted. (Because how often do we second-guess ourselves when things work the way we wanted them to? 🤨)
This is just one of the many reasons mid-year reviews are a powerful tool for experiencing the success you want with money and in life and business.
If I haven’t made a clear case for it previously, I hope today’s missive proves why mid-year reviews are about more than just tracking numbers.
They’re a chance to track your relationship with those numbers — and with the choices that created them.
So, when you reflect on the past six months, ask yourself:
Where did I hesitate to make a move and why?
Where did I not trust myself — and what did that cost me?
What decision am I still judging myself for, even if that outcome wasn’t that bad?
Because making money make sense isn’t just about income or expenses - assets or liabilities.
It’s also about making peace with your choices — and recognizing that every smart move you make starts with trusting yourself to make it.
Regularly doing reviews is an underrated tool for looking forward and making choices with more clarity, rather than too much caution.
If you’d like support doing a mid-year review that looks at both the numbers and the narrative behind them, I still have space for new coaching clients this month. Because this is exactly the kind of clarity work we do inside our 6-month 1:1 coaching program Successful, Profitable…and Not Broke or a Half-Day VIP Coaching Session.
About Jacquette
I love to ask questions and spark aha moments. I love to talk about why success with money is about more than just the numbers, and how the cultural impact on the intersection of money, business, and life matters–A LOT! And, I really hope I help people feel seen, heard, and not judged—especially since money is emotional and personal.
