Money & Mindset ·
Most financial behavior makes more sense when you stop asking, "What's wrong with me?" and start asking, "Where did I learn this?"
What if the reason you keep making the same financial decisions has very little to do with how much you know about money?
Think about it.
You can know exactly what to do. You can have a financial plan, understand the plan, and even agree that it's the right plan. And then turn around and make decisions that take you in the opposite direction.
I've seen this happen countless times in my work.
Someone knows they need to save, but they spend. Someone earns more money than they ever imagined and still feels financially insecure. Someone promises themselves they'll never live the way their parents did and then spends their entire adult life making decisions from that same fear.
We tend to look at those behaviors and assume something is wrong.
Maybe we're irresponsible. Undisciplined. Bad with money.
But what if your financial behavior actually makes sense when you understand where it came from?
That's the conversation I'm interested in.
Listen to the conversation
In this episode of Real Money with Lisa Chastain, I explain how childhood experiences, modeling, beliefs, values, and identity influence our financial decisions. I also share what happens inside a 10 Hour Breakthrough and why understanding your personal history can be an important part of changing your financial behavior.
Most financial advice starts with behavior.
Make a budget. Spend less. Save more. Invest consistently. Pay off debt.
All important things.
But financial behavior doesn't happen in isolation.
Long before you earned your first paycheck or opened your first bank account, you were learning what money meant.
You watched the adults around you.
Who earned the money? Who controlled it? Who worried about it? Who got to spend it?
Did your parents fight about money? Was money something everyone talked about, or was it a subject nobody wanted to discuss?
Was there always enough? Was wanting more considered ambitious or selfish? Were wealthy people admired or criticized?
You were learning.
Not through financial education, but through observation.
And those experiences helped shape the beliefs you eventually carried into adulthood.
In my work, I talk a lot about modeling and reverse modeling.
Modeling happens when we learn behaviors from the people and environments around us.
Reverse modeling happens when we decide we want the opposite of what we experienced.
Sometimes we do both.
I did.
For part of my life, I followed a path that made sense based on what I'd learned about being successful and responsible.
Get a good job. Get married. Have children. Do the right thing.
There was nothing inherently wrong with that life.
But eventually I had to ask myself whether I had chosen it or simply followed the expectations I'd inherited.
We do the same thing financially.
Someone grows up watching their family struggle and makes a decision: I will never be poor.
That decision might drive them to build a successful career, start a business, or accumulate significant wealth.
From the outside, everything looks wonderful.
But internally, they may still live with the same fear that shaped their childhood.
They've changed their financial circumstances without necessarily changing their relationship with money.
Making more money doesn't automatically change what you believe money means.
And that's why someone can have millions of dollars and still feel as though they don't have enough.
One of the principles I work with in my transformational framework is the idea that unresolved experiences and the meanings we attach to them can continue influencing our decisions.
Sometimes we repeat what feels familiar, even when the circumstances are no longer the same.
The people change. The income changes. The relationships change.
And somehow we find ourselves in the same situation.
Someone who learned that love requires financial sacrifice may find themselves repeatedly supporting other people financially, even when they cannot afford to.
Someone who associates success with rejection may find themselves pulling back whenever a new opportunity appears.
Someone who experienced financial instability as a child might spend decades building wealth while still feeling terrified of losing it.
From the outside, these decisions can appear irrational.
But when we understand the beliefs underneath them, the behavior begins to make sense.
That doesn't mean every difficult experience happens for a reason or that we consciously choose painful circumstances.
It means the interpretations we develop from our experiences can continue influencing us long after those experiences have ended.
And if we never examine those interpretations, we may keep making decisions based on them.
I had an experience with a 20-year-old client that illustrates this beautifully.
He was trying to decide what direction to take his career.
Rather than immediately helping him create a plan, I asked him to describe the life he wanted.
Where would he live? What would he do for work? What would success look like? How would he spend his time?
As he answered, I wrote everything down on a yellow sheet of paper.
When we finished, I turned the paper around and asked him one question.
"Whose life is this?"
He looked at the page.
Then he looked at me.
And then he realized.
It was his dad's life.
He had described a future that wasn't actually what he wanted. It was simply the version of success he had learned to recognize.
That's what awareness can do.
It gives us an opportunity to see the difference between what we've been conditioned to want and what we actually want.
And once we recognize the difference, we have a choice.
Podcast episode
Whose Life Is This? | The 10-Hour Breakthrough
Another example comes from my work with Makayla during her 10 Hour Breakthrough.
When she was 15, she started working. Difficult circumstances in her family meant that money from her job was used to help support the household.
Imagine the meaning a teenager might make from that experience.
Years later, she was married, building a business, and struggling financially.
As we explored her personal and financial history, she began recognizing a connection between having money and the possibility of becoming disconnected from the people she loved.
Having money had become associated with responsibility for others.
Protecting herself financially could mean setting boundaries.
And boundaries could feel like losing connection.
Underneath her financial decisions was a belief that sounded something like this:
I can have money, or I can have love.
Think about what happens when someone carries that belief into adulthood.
Making more money may not feel entirely safe.
Saying no may feel selfish.
Creating financial independence may feel like a threat to belonging.
That's not a problem you solve simply by handing someone another spreadsheet.
The work is helping them recognize the belief and decide whether it still deserves a place in their life.
This is where Financial Emotional Intelligence becomes so important.
Financial Emotional Intelligence isn't about eliminating emotions from financial decisions.
It's about understanding how emotions, beliefs, identity, experiences, and personal values influence those decisions.
In the framework I've developed for my work, awareness and personal responsibility are central.
You have to be willing to recognize the patterns influencing your choices.
You also have to be willing to take responsibility for the decisions you're making today.
And those are two different things.
Taking responsibility doesn't mean blaming yourself for everything that's happened to you.
It doesn't mean pretending your circumstances didn't matter.
It means recognizing that regardless of where a belief originated, you now have an opportunity to examine it.
You can decide whether it still serves you.
You can make a different choice.
Personal responsibility is not the same thing as self-blame.
That distinction matters.
There are different levels at which we can create change.
We can change our environment.
We can change our behavior.
We can develop new skills and capabilities.
But we also have to look at our values, beliefs, and identity.
Think about the person who believes they're irresponsible with money.
They might download a budgeting app, hire a financial advisor, or take a financial education class.
Those tools can be helpful.
But if their underlying identity remains, "I'm terrible with money," that belief may continue affecting how they interpret their choices and setbacks.
The same is true for someone who believes they'll never have enough.
They might double their income.
They might build substantial savings.
They might reach every financial goal they originally set.
And still feel financially insecure.
Because the numbers have changed, but the internal conversation hasn't.
This is why I believe financial education and behavioral transformation belong together.
We need practical money skills.
We also need to understand the person using those skills.
I think we've become very good at identifying everything that's wrong with us.
We give ourselves labels.
I'm a spender. I'm financially irresponsible. I'm an avoider. I'm bad with money.
And then we wonder why changing our behavior is so difficult.
What if you became curious instead?
What if you stopped treating every financial mistake as evidence of a character flaw?
What if you began asking questions about the experiences and beliefs influencing your decisions?
Where did I learn this?
Whose expectations am I trying to meet?
What do I believe money will give me?
What am I afraid might happen if I become financially successful?
What have I made money mean about who I am?
Those questions won't replace financial planning.
But they can help you understand why certain financial decisions have been so difficult to change.
And that understanding gives you somewhere new to begin.
We often think of personal transformation as something dramatic.
A big emotional release. A powerful experience. A moment when everything suddenly changes.
Sometimes it is.
But sometimes a breakthrough is much quieter.
It's realizing you've spent 20 years trying to prove something to someone.
It's recognizing that you built a career based on somebody else's definition of success.
It's understanding why having enough money still doesn't feel like enough.
It's seeing that you've been repeating a pattern because you never recognized it as a pattern.
And suddenly, what once felt automatic becomes something you can examine.
You may still need to do practical work. You may need new financial habits, better boundaries, professional guidance, or a different strategy.
But now you're making those decisions with greater awareness.
That's a very different starting point.
If you're tired of repeating the same financial behaviors, I would encourage you to start with curiosity rather than judgment.
Look at the places where you keep experiencing frustration.
Maybe you continually reach the same income ceiling.
Maybe you earn more but still don't feel financially secure.
Maybe you're successful in your career but have a difficult time making financial decisions for yourself.
Maybe you're constantly helping other people financially and have very little left for your own goals.
Or maybe you simply know what to do with your money but struggle to follow through.
Instead of immediately reaching for another solution, ask yourself what you've been believing about money.
What feels familiar about this situation?
Where did you first learn that belief?
And does it still reflect what you actually want for your life?
You don't have to resolve everything in one conversation.
The point is to begin recognizing the difference between the financial circumstances you're experiencing and the beliefs through which you're interpreting them.
Money has a way of revealing what's happening underneath the surface.
Our fears. Our expectations. Our need for security. Our relationships. Our values. The things we believe about ourselves.
That's why I keep returning to money as a doorway to deeper work.
Not because everything is a money problem.
Because money often helps us see the conversation underneath the conversation.
If you've spent years feeling as though you should be further along financially, or wondering why you keep making decisions you know aren't serving you, consider another possibility.
Maybe you aren't bad with money.
Maybe you've been repeating something you learned a long time ago.
And maybe you're finally ready to look at it differently.
Because sometimes the next step in your financial life isn't another strategy.
It's recognizing the one you've been following all along.
— Lisa
Adapted from my original essay published September 17, 2026, on Substack.
Weekly Letters
Money patterns, the beliefs underneath them, and the conversations most people avoid. Written the way it sounds here — no noise, no urgency.
If you know what to do with your money but find yourself repeating the same decisions, there may be more to explore than the numbers.
Understanding the beliefs and behaviors shaping your financial life can help you begin making different choices.
