01/26/2026
On the Hardest Conversation
A Sunday CEO Journal
One of the hardest conversations I have as a coach doesn’t happen in the gym.
It happens on the couch.
It’s the moment before a woman begins a health and lifestyle transformation—when the conversation turns to money. Not because of the number itself, but because of what that number represents.
I remember the first time I made the decision to invest a significant lump sum into myself.
Not for my kids.
Not for a house.
Not for a car.
Just for me.
$20,000 for mindset coaching.
It was deeply uncomfortable. I remember feeling the weight of it in my chest. Every old belief about responsibility, guilt, and worth came flooding in at once.
But I also knew something else just as clearly:
If I didn’t make that decision, I would stay exactly where I was.
That choice wasn’t for the woman I was at the time.
It was for my future self.
And that’s why this conversation matters so much to me now.
Because this is often the moment where women stop themselves.
They believe that investing in themselves should feel comfortable before they decide.
But if it felt comfortable, it would mean it aligned with who they already are. And transformation doesn’t work that way. You’re not making a decision for the woman you’ve been—you’re making it for the woman you’re becoming.
Something powerful happens the first time a woman invests in herself without needing a justification tied to someone else.
She realizes:
I am worth caring for now.
I am worth saving for now.
I am worth real money now.
That realization cracks something open.
Beliefs shift.
Doors open.
Old patterns—especially the ones rooted in self-neglect—start to loosen.
What’s interesting is how easily we, as women, find ways to make things happen for everyone else. We don’t hesitate when it comes to our children. We rise to the occasion in emergencies. We responsibly plan for future healthcare and retirement.
Yet when it comes to investing in ourselves today, it suddenly feels excessive. Selfish. Hard to justify.
And here’s the part most women don’t expect:
Once you break the pattern of not investing in yourself—once you stop chasing the cheapest option and start choosing quality—the financial part becomes the easiest piece.
The money adjusts faster than the mind.
What takes time is the real work:
Changing habits.
Releasing old identities.
Learning consistency.
Letting go of who you’ve been comfortable being.
The money isn’t the hardest part.
What comes after the decision is.
That’s where accountability matters.
That’s where support matters.
That’s where having a team matters.
This has never been about money for me.
It’s always been about witnessing the moment a woman finally sees herself as worthy of investment—of time, energy, commitment, and care.
Because when women start living from that place of worth, everything changes.
And when more women rise into that truth—
we don’t rise alone.
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