Retirement Tax Planning for Women 55+ in Southwest Florida
Your advisor and your tax strategist are the same person. Finally.
CFP® Professional
CFP® Professional
Enrolled Agent
Fee-Only
Fiduciary
NAPFA Member
Tax Planning + Preparation Integrated
The Gap Between Your Financial Advisor and Your Accountant Is Costing You
Most women approaching retirement have the pieces — a 401(k), a brokerage account, Social Security decisions looming, a tax situation nobody has fully explained. What they rarely have is someone who has looked at all of it at once and built a strategy that makes those pieces work together.
That's what comprehensive retirement planning actually means. Not a one-time document. Not a portfolio review with a side conversation about taxes. A coordinated, ongoing relationship built around every dimension of your retirement — income, investments, taxes, healthcare, estate, and the life decisions that don't fit neatly into a spreadsheet.
At Purposeful Money, that relationship is structured around the Long Run Retirement Method.
What Makes Erin O'Brien Different: CFP® and Enrolled Agent
Most financial advisors are not qualified to prepare your taxes. Most accountants are not qualified to build your retirement income strategy. Erin
O'Brien holds both credentials — and that combination is genuinely rare in Southwest Florida.
What Is an Enrolled Agent?
An Enrolled Agent is a federally licensed tax practitioner admitted to practice before the IRS — the highest credential the IRS grants to tax professionals. Unlike a standard preparer, an Enrolled Agent has demonstrated advanced knowledge of federal tax law through a rigorous examination process and is authorized to represent clients in audits, appeals, and collections.
For a retiree, what this means in practice: your financial advisor isn't just aware of the tax implications of your retirement decisions — she's qualified to handle them directly, prepare your returns, and represent you if a question ever arises with the IRS.
What Is a CFP®?
A CFP® — Certified Financial Planner — has met rigorous education, examination, experience, and ethics requirements to provide comprehensive financial planning. The CFP® designation covers retirement income planning, investment strategy, Social Security analysis, estate coordination, and tax planning as an integrated discipline.
When the same advisor holds both the CFP® and the Enrolled Agent credential, retirement planning and tax planning stop being two separate conversations.
The Hidden Tax Traps of Retirement — and How to Plan Around Them
Retirement income is taxed in ways most people don't fully understand until they're already in it. These are the situations that catch women off guard most often — and where proactive planning makes the biggest difference.
Required Minimum Distributions (RMDs)
Once you reach the required beginning date, the IRS mandates annual withdrawals from your traditional retirement accounts — whether you need the income or not. Those withdrawals are taxed as ordinary income. Taken without a strategy, RMDs can push you into a higher bracket, trigger IRMAA surcharges on Medicare premiums, and increase the portion of your Social Security that's taxed. The planning window for managing RMD impact begins years before distributions are required.
Roth Conversion Strategy
Converting traditional IRA funds to a Roth IRA generates taxable income in the year of conversion — but it reduces future RMDs, creates tax-free income later, and can protect your heirs from inheriting a large tax burden. The question is never whether to convert. It's how much, in which years, at what rate, and how it interacts with everything else on your tax return. That's a calculation that requires seeing both the financial plan and the tax picture at once.
Social Security Taxation
Up to 85% of Social Security benefits can be subject to federal income tax, depending on your combined income. Most people don't learn this until after they've claimed. Understanding how your other income sources interact with your Social Security benefit — and planning your withdrawal sequence accordingly — is one of the highest-value decisions in retirement tax planning.
IRMAA Surcharges on Medicare Premiums
If your modified adjusted gross income exceeds certain thresholds, Medicare adds income-related surcharges to your Part B and Part D premiums. These thresholds can be crossed unexpectedly in years with large Roth conversions, RMDs, or asset sales. Planning your income in advance — and knowing which thresholds to stay under — is part of integrated retirement tax planning.
Florida Residency and Federal Tax Reality
Florida has no state income tax, which is a genuine advantage. But federal taxes on retirement income don't disappear at the state line. RMDs, Social Security, dividends, capital gains, and investment income are all still subject to federal tax — and for women who've recently relocated from a high-tax state, the first year of retirement withdrawals can be a surprise. A coordinated withdrawal strategy minimizes your federal burden year by year, so Florida's tax advantages actually show up in your pocket.
Inherited IRA Rules
The SECURE Act significantly changed how inherited IRAs are taxed for most non-spouse beneficiaries, requiring full distribution within 10 years. If you've inherited a retirement account or expect to, understanding the distribution options and their tax implications is time-sensitive planning — not a question to defer.
What Tax Planning Looks Like Inside a Purposeful Money Relationship
Filing a tax return is not tax planning. Tax planning is the work that happens before the return — the decisions made during the year that shape what's on it.
Inside a Purposeful Money advisory relationship, tax strategy is not a separate engagement or an annual add-on. It's part of every planning conversation throughout the year. That includes:
- Monitoring your income picture across all sources to avoid bracket creep and IRMAA thresholds
- Identifying Roth conversion opportunities in lower-income years before RMDs begin
- Coordinating the timing of asset sales, withdrawals, and distributions to minimize annual tax liability
- Preparing your federal tax return with full knowledge of the retirement income plan — because the advisor and the tax preparer are the same person
- Reviewing tax law changes and adjusting your strategy before they affect your return
Who This Relationship Is Built For
- Women age 55+, approaching retirement or already there
- Households with $1.5 million or more in investable assets
- Women whose financial advisor and accountant have never been in the same room — or conversation
- Anyone who has been surprised by their tax bill in retirement and wants that to stop
- Recent Florida relocators who expected a tax break and are still getting hit harder than anticipated
- Women managing RMDs, a Roth conversion strategy, or an inherited IRA without a coordinated plan
As a
fee-only fiduciary, I earn no commissions on any product. Every recommendation — including every tax decision — is made because it's right for your retirement.
How We Work Together
Step 1:
Your Starting Point
We begin with a conversation about your full income picture — where your money is, what you're drawing from, and what your tax situation looks like today.
Step 2:
Tax and Retirement Income Review
I review your retirement accounts, taxable accounts, Social Security situation, and recent returns to identify where the gaps are and where the planning opportunities exist.
Step 3:
Integrated Tax and Retirement Strategy
I build a coordinated plan that sequences your income, manages your tax exposure year by year, and positions you for the decades ahead — not just the current filing season.
Step 4:
Ongoing Planning and Tax Preparation
As part of the ongoing advisory relationship, I prepare your federal taxes each year with full knowledge of your retirement plan — and adjust your strategy in real time as your life and the tax landscape evolve.
About Erin O'Brien — CFP® and Enrolled Agent in Southwest Florida
- CFP® professional with 25 years of experience in retirement planning
- Enrolled Agent — admitted to practice before the IRS, qualified to prepare and advise on federal 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 women 55+ across Southwest Florida and virtually nationwide
Ready to Stop Being Surprised by Your Tax Bill?
Tax-smart retirement planning starts before the bill arrives — and it works best when the person building your retirement income strategy is also the one doing your taxes. If you're a woman 55+ in Southwest Florida looking for that kind of integrated relationship, let's talk.
Questions About Retirement Tax Planning in Southwest Florida
How do I reduce taxes in retirement in Florida?
Florida's lack of state income tax helps — but federal taxes on RMDs, Social Security, dividends, and capital gains still apply. Reducing your federal tax burden requires a coordinated withdrawal strategy: sequencing income across accounts, identifying Roth conversion windows, timing asset sales, and staying under IRMAA thresholds. That planning works best when your financial advisor and your tax preparer are the same person.
What is an Enrolled Agent and why does it matter for retirement planning?
An Enrolled Agent is a federally licensed tax professional admitted to practice before the IRS — the highest credential the IRS grants. For retirees, it means your financial advisor is also qualified to prepare your taxes and handle any IRS matters directly. That combination — CFP® and Enrolled Agent — is what makes integrated retirement tax planning possible in a single advisory relationship.
When should I take RMDs to minimize taxes?
RMD timing strategy depends on your full income picture — other withdrawal sources, Social Security income, filing status, and whether you're approaching an IRMAA threshold or bracket boundary. The planning for RMD impact typically begins several years before distributions are required, when Roth conversion opportunities are still available.
What is a Roth conversion and should I do one?
A Roth conversion moves money from a traditional IRA — where withdrawals are taxed — into a Roth IRA, where qualified withdrawals are tax-free. The conversion itself generates taxable income, so the question is always how much to convert, in which years, and how it interacts with your other income. Done strategically, conversions can reduce future RMDs, lower your long-term tax burden, and create tax-free income later in retirement.
Can my financial advisor also do my taxes?
Most cannot. Erin O'Brien holds the Enrolled Agent credential in addition to the CFP® designation, which is what makes it possible to prepare your federal taxes and build your retirement income strategy in the same relationship — with full visibility into both sides of your financial picture.
Is there an enrolled agent and CFP doing retirement planning in Southwest Florida?
Yes. Purposeful Money is based in Naples and serves women 55+ across Southwest Florida. The combination of CFP® and Enrolled Agent credentials is rare in this market — and it's what makes integrated retirement tax planning possible without splitting your financial life between two separate advisors.
