A More Thoughtful Approach to Retirement
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Olga Livesey Photography
Helping Women Navigate their Season of You™
Retirement isn’t just about money; it’s about peace of mind. It’s about knowing you’re going to be okay, that you won’t outlive your savings, and that your future is aligned with the life you actually want to live.
Over the years, I've seen too many women step into retirement carrying more worry than freedom. The numbers might be there on paper, but the deeper concerns still linger:
Will I have enough?
What am I missing?
Who can help me make these decisions with clarity and care?
That's why my work is centered on helping women move through their Season of You™ with both confidence and calm.
With 25 years of experience in wealth management, I combine retirement planning, investment guidance, and integrated tax strategy and preparation with a deeply personal approach centered on the individual behind the portfolio.
And as a fee-only fiduciary planner, you can be sure that your best interests are at the heart of all I do.
Life-Centered Guidance for Your Next Chapter
Working with us means:
Partnership First.
You’re never just a number on a spreadsheet. We're here to listen, explain, and help you feel supported and informed through every stage.

For married clients, that partnership includes both spouses; creating space for open conversations, shared decision making, and a retirement plan that supports your goals together.
Purpose-Driven Planning.
Money isn’t the end goal — it’s a tool to support the life you want to live.
Together we'll explore questions like:
- What do you want your days to look like?
- What brings you joy, meaning, and connection?
- How do you want to use your time, talents, and resources in this next season of life?
Peace of Mind.
Whether it's an everyday question or a major life decision, you'll have a trusted partner for clear, practical guidance.
My approach to retirement planning and wealth management is holistic– blending financial expertise with life planning to ensure your retirement is both secure and fulfilling.
Why This Work Matters to Me:
Shaped by Experience, Driven by Purpose
When I first entered this field, I quickly learned how broken the traditional financial model was. Advisors were pressured to “sell products,” not truly help people. That never sat right with me.
When my own family went through a personal crisis after a devastating loss, I saw firsthand how overwhelming it can feel to make big financial decisions in a vulnerable moment. What my family needed wasn’t jargon or sales pitches — we needed someone to listen, to meet us where we were, and to walk with us step by step.

That experience shaped everything about how I serve my clients today: with empathy, clarity, and a focus on the whole person behind the portfolio.
Erin O’Brien, CFP®
President and Certified Financial Planner™
For more than 25 years, Erin has helped clients through one of life’s most meaningful transitions: retirement. As a fiduciary Certified Financial Planner™, Accredited Wealth Management Advisor, and Enrolled Agent admitted to practice before the IRS, she combines investment guidance with integrated tax planning designed to support long term financial confidence.
But what truly defines Erin's approach is her belief that retirement planning should support the life you truly want to live, not simply numbers on a spreadsheet.
Working primarily with women in their 50's and beyond, Erin calls this stage of life the Season of You™; a season centered on clarity, purpose, freedom, and thoughtful planning for the years ahead.
“I find great satisfaction serving as a woman’s financial partner and go-to, building relationship and supporting her through all the ups and downs life and finances bring — whether it’s practical things like explaining a mortgage disclosure in plain English or filling out paperwork together; or the more soulful questions like where would she love to live at this stage of her life or how to balance helping her kids while keeping her future secure. That’s the stuff that keeps me saying I have the best job in the world.”
Memberships & Designations
- Certified Financial Planner™ (CFP®)
- Enrolled Agent (EA), admitted to practice before the IRS
- Accredited Wealth Management Advisor (AWMAâ„ )
- NAPFA Registered Member
- Member of the XY Planning Network
Seamless Operational Support
Purposeful Money partners with the Sapphire Team to handle the operational details, from paperwork to processing. Their work ensures every account is managed with care, precision, and responsiveness.
Beyond the Numbers
Erin lives in Naples, Florida, with her husband and their beloved pups, in the home they affectionately call Holiday House. Family and faith are at the heart of her life.
Outside of work, she enjoys running, baseball, golf, the beach and time spent with her children and grandchildren.
One of the greatest joys of Erin's career has been the long term relationships she's built with clients over the years. Whether it’s swapping stories about kids, celebrating a trip, or hearing about the next big dream, those personal connections are what make this work so meaningful.
At the end of the day, financial planning isn't just about money. It's about creating a life that feels intentional, secure, and deeply fulfilling through every season ahead.
You deserve more than a financial plan. You deserve a partner who listens, understands, and helps you step into retirement with confidence.
