Retirement Planning for Women 55+ in Naples, FL

Naples-based retirement planning built for the life you actually want — from a fee-only fiduciary CFP® who also does your taxes.

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CFP® Professional

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CFP® Professional

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Enrolled Agent

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Fee-Only

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Fiduciary

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NAPFA Member

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25 Years of Experience

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Based in Naples, FL

Does Any of This Sound Familiar?

You may be wondering:

  • Can I actually afford to retire in Naples on what I've saved?
  • How do I turn my savings into reliable income that lasts?
  • When should I claim Social Security — and how will it affect my taxes?
  • Is there someone in Naples who can connect my retirement plan and my tax strategy?
  • Am I making the right decisions after a divorce, a loss, or a big life change?

Naples Is One of the Best Places to Retire — and One of the Most Complex to Plan For

Naples has a median age of around 67 and one of the highest concentrations of retirees in the country. The cost of living here is real — especially for healthcare, housing, and the lifestyle that drew you here in the first place. And for seasonal residents splitting time between Florida and another state, the tax picture gets more layered, not less.


Retirement planning in Naples isn't just about the numbers. It's about building a plan that works for how you actually live here — whether that means managing a second home, navigating Florida's property tax rules, or making sure your income strategy accounts for the months you're somewhere else.


That's work that requires someone who knows this market and knows how to connect the financial and tax pieces in one coherent plan.

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One Advisor. Your Retirement Plan, Your Investments, and Your Taxes — Together.

Most people in Naples have a financial advisor. Far fewer have one who also prepares their taxes. That gap is where retirement gets complicated.

I hold both the CFP® designation and the Enrolled Agent credential — which means I'm qualified to build your retirement income strategy and handle your tax planning and preparation in the same relationship. Nothing falls through the cracks because there's no gap between your advisor and your tax preparer. They're the same person.

Retirement Income Planning

Your savings need to become reliable income. I help you build a drawdown strategy that accounts for Social Security timing, RMDs, Roth conversions, and what Naples life actually costs.

Investment Management

Your portfolio should match your income needs, your risk comfort, and your timeline — not a generic allocation built for someone else's retirement.

Tax-Smart Strategy

From Social Security taxation to capital gains to estate coordination, every planning decision I make is made with your tax picture in mind.

Who Purposeful Money Is Built For

  • Women and couples age 55+, approaching retirement or already there
  • Households with $1.5 million or more in investable assets
  • Anyone who wants retirement planning, investment management, and tax strategy coordinated in one relationship
  • Seasonal Naples residents who need planning that accounts for multi-state living
  • People who are tired of talking to advisors who want to sell them something


As a fee-only fiduciary, I earn no commissions — on anything. My only job is to give you advice that's right for you.

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How We Work Together

Step 1:

Your Starting Point

We start with a conversation — where you are, what's changing, and what questions are keeping you up at night. No pitch. No pressure.

Step 2:

Your Full Retirement Picture

I review your income sources, investments, tax situation, cash flow, and long-term needs — then show you where things stand and where gaps exist.

Step 3:

An Ongoing Planning Relationship

If we're a fit, we work together over time. Planning, investments, taxes, and life-event guidance — all in one place, all coordinated, all the time.

About Erin O'Brien — Fee-Only Fiduciary in Naples, FL

  • CFP® professional with 25 years of experience
  • Enrolled Agent — qualified to prepare and advise on taxes
  • Fee-only fiduciary — no commissions, no conflicts, legally obligated to act in your best interest
  • NAPFA member and XY Planning Network member
  • Based in Naples, serving clients locally and virtually across the country
  • Focused exclusively on women and couples navigating retirement

Ready to Stop Wondering and Start Planning?

You've worked too hard to leave your retirement to chance — or to an advisor whose interests aren't fully aligned with yours. If you're looking for fee-only, fiduciary retirement planning in Naples from someone who also handles your taxes, let's talk.

Questions About Working With a Naples Retirement Planner

  • Do I need to live in Naples to work with you?

    No — Purposeful Money is based in Naples and serves clients locally and virtually nationwide. Many clients are seasonal Naples residents who split their time between Florida and another state.

  • Do you only work with women?

    I specialize in helping women 55+ navigate retirement, and I regularly work with couples as part of that relationship. The planning focus is always on the woman as the primary client.

  • How is a fee-only fiduciary different from a typical financial advisor?

    A fee-only fiduciary earns no commissions on any product — ever. I'm paid directly by you, which means my advice is never influenced by what earns me the most. I'm also legally obligated to act in your best interest, not just recommend something "suitable."

  • Do you prepare taxes?

    Yes. As an Enrolled Agent, I'm qualified to prepare federal taxes and advise on tax strategy. That credential is what allows me to integrate retirement income planning and tax planning in one relationship rather than keeping them separate.

  • What's Naples retirement planning actually like with Purposeful Money?

    It starts with a conversation about your situation — not a sales presentation. If we're a good fit, we build a retirement income plan, manage your investments, and handle your taxes together, over time, as your life evolves.

  • Who is the best fee-only financial advisor in Naples, Florida?

    The right advisor for you is a fiduciary who's legally obligated to act in your interest, holds credentials that go beyond a standard license — like CFP® and Enrolled Agent — and specializes in the kind of planning you actually need. If you're a woman approaching or living in retirement, I'd be glad to have that conversation.

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Inheriting Money? Start Here.

Inheriting money is one of the most emotionally complex financial events you can face — and one of the least talked about. Erin O'Brien breaks it down into the most common inherited assets and the rules, questions, taxation, and actions to take. 


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