Money & Confidence: What Actually Helped Me

Hi Friend,

I was genuinely touched by the response Part 1 of this month's newsletter.

So many of you reached out to tell me you saw yourselves in that story. Some shared that you've always left the finances to your partner. Others said you've been quietly trying to learn but still feel overwhelmed. And many of you simply thanked me for talking openly about something we don't discuss nearly enough.

It reminded me that this conversation isn't really about money.

It's about confidence.

It's about having choices.

It's about trusting yourself to step into parts of life that once felt intimidating.

None of us are expected to know everything. We just have to be willing to stay curious and take the next step.

That got me thinking...

If I could go back seven years and sit down with the version of me who was staring at spreadsheets wondering where to begin, what would I tell her?

Here's what comes to mind.

Why This Matters

Money is rarely just about money.

It's about understanding your options.

Feeling confident enough to ask questions.

Making decisions from a place of clarity instead of avoidance.

Whether you're married, divorced, single or somewhere in between, taking ownership of your finances isn't about becoming an expert.

It's about becoming more engaged in your own life.

Because every decision you make strengthens something much bigger than your bank account.

It strengthens your trust in yourself.

What Actually Helped Me
Build That Confidence

1. Ask the questions.

I stopped worrying about looking uninformed and started asking the questions I needed answered. Every conversation taught me something new and helped me make better decisions.

2. Know your numbers.

I put everything in one place so I could see my full financial picture. Clarity replaced the stories my mind was making up. (I use the Monarch finance app.)

3. Make it a monthly habit.

I review my finances every month. Not because I enjoy spreadsheets, but because staying engaged helps me feel informed, intentional and in control. It also helps keep those pesky critical stories at bay - I lean on the facts.

4. Learn from people you trust.

I surrounded myself with advisors and people who were willing to explain things without judgment. You don't have to figure everything out on your own.

5. Remember: confidence follows action.

I didn't wake up one day feeling financially confident. Confidence grew every time I asked a question, made a decision or learned something new. It was built one step at a time.

Thank you for being part of this community.

Every reply to these newsletters reminds me that when one woman is willing to speak honestly about what she's learning, it gives someone else permission to begin too.

I hope this conversation encourages you to keep taking ownership of the parts of your life that matter most to you.

One decision at a time.

Lucy

P.S. If this landed, you’re not alone.
So many women are sitting in this exact space right now.

And sometimes one honest step is all it takes.
Please share. They can subscribe here.

P.S.S. How I Can Support You in 2026

If you’re a woman who knows something has to change, but you’re still stuck in the “thinking about it” phase and want to experience clarity, confidence, and real momentum instead, I invite you to…

→ Start with a 30min Fit Call

We’ll name exactly where you are, what’s keeping you stuck, what needs to shift and if I am the right support for you.

→ Next Chapter Roadmap (90min 1:1 intensive)

Deep dive to cut through the noise and map your next step

→ 1:1 Coaching (Next Chapter Catalyst)

Where we build real, lasting change - with support and accountability

Lucy Regan

18 Bayview Avenue
Mill Valley, CA 94941, United States