What Are You Really Working For? How to Reconnect With Your ‘Why’ When Money Feels Heavy
- Davina Jackson
- May 23
- 9 min read
Welcome to The Woman CFO – a space crafted just for you, where we help you take control of your money, heal your financial past, and create a financial future you love.
When Money Feels Heavy, It’s Time to Pause
There’s a point where the grind stops feeling good.
You’re doing the budgeting. You’re meeting the goals. You’re “managing” just fine.
And yet… it still feels heavy.
Heavy like you’re always pushing but never resting.
Heavy like the peace you thought money would bring but keeps getting pushed further down the line.
This is the part we don’t talk about enough: what happens when money stops feeling like a tool and starts feeling heavy like a burden?
The answer isn’t that you’re doing it wrong. It’s that you might be disconnected.
Disconnected from the vision you started with.
Disconnected from the purpose behind your hustle.
Disconnected from your financial why.
If money has started to feel heavy - like pressure instead of peace - this post is for you.
Let it be your invitation to pause, reconnect with your financial why, and reset your money goals to support the life you actually want.
Not with more rules or pressure.
But with clarity and a plan that actually feels good.
Because real financial progress isn’t just about how much you earn, save, or invest.
It’s about how aligned it feels while you do it.
Key Points
When money feels like pressure instead of power, it’s time to pause and reflect.
Many women are managing money well but still feel burnt out, stressed, or disconnected.
Reconnecting with your “why” helps realign your goals with the life you actually want.
Money should support your peace, not constantly challenge it.
You’re allowed to reset. This post helps you do that with clarity and intention.
Psst... There’s a free, fillable Financial Reset Journal worksheet waiting for you at the end. I designed it to help you realign your money goals with what actually matters to you right now.
Instant Gratification Zone: Skip to the Good Stuff
The Weight Women Carry Around Money
Money doesn’t just live in your bank account.
It lives in your body. In your to-do list. In your group chat. In the middle of your thoughts when you’re trying to sleep.
For most of us, money is more than just numbers. It’s pressure, protection, and proof that we’re doing everything we’re “supposed to.”
And it’s often the thing we’re silently managing while holding up everything else.
We’re not just working to pay bills.
We’re working to close wage gaps.
To show up for aging parents.
To bounce back from financial curveballs no one sees coming.
To fund our freedom and everyone else’s safety net.
And that weight? It’s so very real.
Even when you’re good with money and you’ve got a plan.
The mental and emotional labor of managing it all can leave you feeling burnt out, disconnected, and quietly resentful.
You might be saving diligently but feeling restricted.
You might be hitting financial goals, but they don't mean anything to you anymore.
You might be budgeting like always (even though your life has changed).
But when your money starts to feel heavy, it's not just a financial issue.
It's a sign.
Something deeper is asking for attention, and more often than not, that something is your why.
Before you open another spreadsheet or recommit to a goal that no longer fits, take a breath. This is your moment to reconnect with your financial why.
To pause the performance and check in with what actually matters to you.
Because carrying the weight is one thing.
But carrying it without clarity? That’s the kind of burnout that doesn't fade easily.
You have to understand that financial heaviness is rarely about the dollars.
It's about disconnection: from your goals, your vision, and the 'why" you started with.
So before you keep pushing forward, pause.
And ask yourself: What am I really working toward?
Ask Yourself: What Am I Really Working Toward?
Sometimes we’re chasing goals we set five years ago.
Sometimes we’re chasing goals someone else told us we should want.
And sometimes, we’re just chasing without ever stopping to ask why.
That’s where the disconnect begins.
You’re doing all the things: saving, investing, budgeting - yet the joy, motivation, and clarity just aren’t there.
So what gives?
Signs you’ve drifted from your financial why:
You hit a money milestone… and still feel anxious.
You avoid looking at your accounts, even though nothing is technically “wrong.”
Your goals sound good on paper but feel heavy, rigid, or irrelevant in real life.
These are red flags that you're operating from habit, hustle, or pressure - not from purpose.
It's time to get honest with yourself.
Ask yourself: What do I want my money to make possible for me right now?
Not what you used to want.
Not what looks good on your vision board.
But what you actually need, value, and crave in this current season of life.
That’s how you start to reconnect with your financial why: by shifting the focus from external validation to internal alignment.
Because when your money goals are rooted in what’s real for you (not what’s expected of you) everything changes.
You stop managing your finances from a place of fear or guilt, and start building from a place of clarity and ownership.
And this isn’t about scrapping your whole plan.
It’s about making sure your plan still fits the woman you’re becoming.
Once you’ve reconnected with your why, the next step is just as powerful: reframing your relationship with money. Not as something to conquer, but as something that supports you.
Reframing Money as a Support System (Not a Stressor)
Once you’ve reconnected with your financial why, the next step is to reframe your relationship with money itself.
Because here’s the truth: money is not just something to manage. It’s something to design with.
If your current money plan feels like a weight you’re dragging behind you, it's probably time to shift how you see it.
Money isn’t just here to pay bills, check boxes, or keep you “responsible.” It’s here to support your life.
And not just the version of your life that looks productive and polished, but the version that gives you freedom, rest, space, and joy.
This is where a lot of us get stuck. We’re so used to associating money with stress or sacrifice that we forget: money can be a support system.
A resource for ease.
A structure for peace.
Ask yourself:
What would it look like if my money goals created breathing room, not pressure?
What would I change if I believed I didn’t have to earn ease but could build it in?
Because when your financial plan reflects your values (not just your obligations) it starts to feel lighter, more aligned, and actually worth sticking with.
You stop budgeting just to survive and start planning to thrive.
You stop chasing “enough” and start building from what matters.
Try This Quick Exercise
List 3 values you want your money to reflect
Examples:
Freedom: flexibility to make life decisions without fear
Safety: knowing you have a cushion if things go left
Joy: spending on things that bring genuine ease, not just status
Now ask yourself: Are my current financial goals set up to support these values?
If the answer is no, that’s your signal.
It's time to shift something - big or small.
Because when you reconnect with your financial why and give your money a purpose that’s rooted in your life (not someone else’s version of success) you don’t just regain control.
You get clarity. You gain momentum. And you gain a reason to keep going.
Your money shouldn’t constantly challenge you.
It should stand with you.
And that’s what we'll talk about next: how to reset your goals so they reflect who you are now and where you're actually headed.
Resetting Your Relationship with Your ‘Why’
Once your values are clear, the goal isn’t to go back to the old plan.
It’s to create a new one. One that actually supports the life you're living today, not the version of you that created your budget three years (or three burnout cycles) ago.
This is your invitation to reset.
Not from scratch but with more intention.
Because the real win isn’t just being consistent.
It’s being aligned.
And the most powerful way to reconnect with your financial why is to make sure your goals reflect the woman you are now - not the one you’ve been trying to keep up with.
Try This 3-Step Reset
Step 1: Write down 3 things you want more of in your life right now
Think:
Rest
Travel
Security
Time with your people
Peace of mind
Joy that doesn’t come with guilt
Step 2: Look at your top 3 money goals
Ask yourself: Are these actually helping me create more of what I want?
Or are they draining me while I chase someone else’s timeline?
Step 3: Choose one goal to reframe today
Example shifts:
From “Pay off all debt this year” → to “Build a sustainable debt plan that also honors my need for joy.”
From “Hit a six-figure income” → to “Grow my income while keeping my schedule sane.”
This is how your why evolves with you.
And when your goals feel personal again, motivation isn’t something you have to chase.
It flows because the plan finally makes sense again.
Your money goals should reflect your growth, not punish your pace.
Because it’s not just about what you’re working toward. It’s about how you feel while you’re working.
And that leads us to the most important part of all: giving yourself permission to reset and build a financial life that actually moves with you.
What's Next After Reconnecting with Your Financial 'Why'?
Clarity is a turning point but it doesn’t create change on its own.
What you do with that clarity is what shifts your direction.
This isn’t about scrapping your entire plan or chasing a new version of perfection.
It’s about choosing one intentional step that aligns with where you’re headed (not where you’ve been stuck).
That could mean:
Letting go of a goal that no longer fits
Adjusting your budget to reflect your current values
Setting boundaries that protect your time, income, or peace
Because alignment isn’t a one-time decision. It’s something you practice.
And that practice starts with reflection.
Before you rush into a new to-do list, take a moment to check in:
Journaling Prompt: What’s one small change I can make this week that would bring my money goals closer to how I want to feel in my life?
You Deserve Money That Moves With You
This isn’t about tossing your goals in the trash.
It’s about making sure they still fit you - not just the version of you that built them in survival mode.
Because money isn’t just about getting ahead.
It’s about feeling clear, supported, and aligned while you build the life you want.
You don’t need financial goals that look impressive but drain your energy.
You don’t have to keep grinding toward numbers that no longer feel connected to your values.
And you definitely don’t need to carry shame just because you want things to feel better not just bigger.
Because real wealth isn’t just what you build.
It’s how you feel while you’re building it.
So if money has started to feel heavy, take this as your permission to pause.
Reflect. Reset.
Reconnect with your financial why and start building a plan that actually moves with your life.
Remember, you’re not falling behind. You’re evolving.
And your money should, too.
Free Download: The Financial Reset Journal Page
Feeling disconnected from your money goals?
This fillable, guided worksheet will help you realign your financial priorities with your current season of life without guilt, overwhelm, or hustle.
Inside you’ll find:
Reflection prompts to uncover what’s actually feeling off
A reset space to rewrite your financial focus with clarity
A values-based goal check-in
Plus: A 5% off code to use on any journal or notebook from The Woman CFO's stationary shop, The Paper Suite
Start fresh. No pressure. Just clarity that feels like peace.
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