Erin O'Brien, CFP® and Enrolled Agent
Fee-Only Fiduciary Financial Advisor in Naples, FL
A retirement planning partner whose only job is to help you.
Credit
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, I combine
retirement planning, investment management, and
integrated tax strategy and preparation with a deeply personal approach — built around the individual behind the portfolio, not just the numbers in front of her.
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.”
The Credentials That Change What Retirement Planning Can Do For You
Most financial advisors manage investments. Some build retirement income plans. Almost none also prepare your taxes. Erin O'Brien does all three — and the credentials behind that are specific, meaningful, and rare in the Naples and Southwest Florida market.
Fee-Only Fiduciary
"Fee-only" means Erin earns no commissions, accepts no referral fees, and receives no compensation from any financial product — ever. Her only source of revenue is the fee paid directly by her clients.
"Fiduciary" means she is legally obligated to act in your best interest at all times — not just to recommend something that qualifies as suitable. Combined, these two standards mean there is no version of this relationship where Erin's financial interest conflicts with yours.
Purposeful Money is a NAPFA Registered Member firm. NAPFA — the National Association of Personal Financial Advisors — is the leading professional association for fee-only financial advisors, and membership requires adherence to a fiduciary oath and ongoing fee-only standards.
CFP® — Certified Financial Planner™
The CFP® designation is one of the most rigorous credentials in financial planning — requiring thousands of hours of education and experience, a comprehensive examination, and ongoing ethics and continuing education requirements. It covers retirement income planning, investment strategy, tax planning, estate coordination, Social Security analysis, and Medicare guidance as an integrated discipline.
Enrolled Agent — Admitted to Practice Before the IRS
An Enrolled Agent is a federally licensed tax professional who has passed a comprehensive IRS examination covering all aspects of federal tax law. Enrolled Agents are authorized to represent clients before the IRS in audits, appeals, and collections — the highest tax credential the IRS grants to non-attorney practitioners.
For Erin's clients, the practical meaning is this: the advisor building your retirement income strategy is also qualified to prepare your federal tax returns, advise on Roth conversions and RMD strategy, and represent you if the IRS ever raises a question. There is no handoff to a separate accountant because there is no gap between your retirement plan and your tax plan.
AWMA℠ — Accredited Wealth Management Advisor
The AWMA℠ designation reflects advanced training in wealth management strategies for high-net-worth clients — including complex asset structures, estate planning considerations, and investment strategies for the distribution phase of retirement.
XY Planning Network Member
The XY Planning Network is a fee-only advisory network with a fiduciary membership standard. Membership requires fee-only compensation practices and ongoing adherence to client-first planning principles.
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.
Ready to Work With a Fee-Only Fiduciary Who Actually Does It All?
You deserve an advisor whose only job is to help you — one who earns nothing from what she recommends, is legally obligated to act in your interest, and brings CFP® and Enrolled Agent credentials to every retirement and tax decision you face.
If you're a woman 55+ in Naples or Southwest Florida looking for that kind of relationship, let's start with a conversation.
