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Purposeful Money Helping women step into their Season of You™ with clear, tax-smart retirement guidance and peace of mind. Led by Erin O'Brien, CFP, EA

10/25/2026

Rolling your Publix stock into an IRA could cost you six figures 👀

Most people leaving Publix default to the IRA rollover, and on the surface it makes sense.

But here's what that choice quietly does: it erases the tax character of all the growth you've built up in your company stock. Every dollar you withdraw later gets taxed as ordinary income, potentially up to 37%.

There's a second path most people never hear about before they sign the rollover paperwork.

It's called Net Unrealized Appreciation, or NUA. Instead of rolling your shares into an IRA, you move them in kind to a taxable brokerage account. You pay ordinary income tax on just the original cost basis at distribution. The built-up growth? That gets taxed at long-term capital gains rates when you eventually sell, which in 2026 are 0%, 15%, or 20% depending on your income.

On a large Publix position with a low cost basis, the difference between these two paths can easily be six figures over your lifetime.

Not everyone qualifies, and the timing has to be deliberate. But if you're approaching retirement with significant Publix stock, it's worth knowing this option exists before you make a move you can't undo.

Privacy Policy and Disclosures/Terms of Use documents are linked in the website footer. Disclosures document URL: https://irp.cdn-website.com/0b5a1e75/files/uploaded/DISCLOSURES+-+TERMS+OF+USE+-+PURPOSEFUL+MONEY.pdf. Privacy Policy URL: https://irp.cdn-website.com/0b5a1e75/files/uploaded/Privacy-Policy-Updated.pdf. CFP® and Certified Financial Planner™ marks used with trademark symbols throughout.

Purposeful Money is a financial advisor serving women in their 50s and beyond approaching or already in retirement.

On October 14, 2026, the Social Security Administration (SSA) announced a 3.6% cost-of-living adjustment (COLA) for 2027...
10/20/2026

On October 14, 2026, the Social Security Administration (SSA) announced a 3.6% cost-of-living adjustment (COLA) for 2027, marking the largest increase in Social Security benefits since 2023.

With this adjustment affecting approximately 76 million Americans receiving Social Security or Supplemental Security Income (SSI) benefits, we wanted to share a breakdown of what's changing, how it may impact your finances, and a few important considerations for 2027. Swipe to learn more.

If you'd like to discuss how these changes may affect your retirement income, budgeting, or overall financial plan, we’d be happy to help. Feel free to give us a call to set up a time to connect.

Estate Planning Awareness Week is a valuable reminder that your estate plan should evolve alongside your life, wealth, a...
10/20/2026

Estate Planning Awareness Week is a valuable reminder that your estate plan should evolve alongside your life, wealth, and retirement goals.

For women approaching or living in retirement, legacy planning often involves more than having a will. It can mean coordinating beneficiary designations, preparing for incapacity, considering tax implications, and ensuring the people you love understand your wishes.

In the carousel, I am sharing several estate planning considerations that can help bring greater clarity to your plan.

Estate planning is not just about documents. It is about creating confidence that your financial life and your legacy reflect what matters most to you.

If you would like help coordinating estate planning with your retirement, investment, and tax strategy, I would be glad to talk.

10/20/2026

Still holding onto tax returns from the 90s? 🗂️

You might be keeping a lot more paperwork than you actually need.

The IRS has specific windows for how long you're required to hold onto returns, and once you know them, clearing out that old paperwork feels a lot less overwhelming.

Here's a quick breakdown:

3 years from your filing date covers most standard returns with no issues.

6 years applies if you accidentally left out more than 25% of your gross income, something that can happen more easily than you'd think with freelance or rental income.

If a return was never filed or fraud was involved, there's no statute of limitations. Those you keep indefinitely.

Property records, including your home and investment accounts, should be kept while you own them and for at least 3 years after you sell.

And if you ever took a bad debt deduction or wrote off a worthless investment, hold those records for 7 years.

Knowing your actual window is the first step to finally clearing out that old shoebox.

Which category do you think applies to your situation? Drop it in the comments!

Privacy Policy and Disclosures/Terms of Use documents are linked in the website footer. Disclosures document URL: https://irp.cdn-website.com/0b5a1e75/files/uploaded/DISCLOSURES+-+TERMS+OF+USE+-+PURPOSEFUL+MONEY.pdf. Privacy Policy URL: https://irp.cdn-website.com/0b5a1e75/files/uploaded/Privacy-Policy-Updated.pdf. CFP® and Certified Financial Planner™ marks used with trademark symbols throughout.

Purposeful Money is a financial advisor serving Women in their 50s and beyond approaching or already in retirement. Specific client markets include: Baby Boomers, Generation X, singles (widowed, divorced, never married). Clients generally have at least $1.5 million in investable assets or meet a $15,000 annual minimum fee. Married couples are also served, with both spouses included in the planning partnership.

Retirement is more than a financial milestone. It is an opportunity to shape what comes next around the life you want to...
10/19/2026

Retirement is more than a financial milestone. It is an opportunity to shape what comes next around the life you want to live.

For women over 50, a confident retirement strategy should bring together:
• Sustainable retirement income
• Investment management aligned with your goals
• Tax-smart withdrawal planning
• Social Security and Medicare decisions
• Legacy and estate planning coordination
• The freedom to explore your next season with purpose

During National Retirement Security Week, I am reminded that true retirement readiness is not just about reaching a number. It is about having a clear plan, understanding your choices, and feeling supported as life evolves.

At Purposeful Money, I use my Long Run Retirement Method to help clients create a plan that supports both their financial security and their Season of You™.

If you are approaching retirement or recently retired, let us talk about whether your current strategy reflects the future you envision.

10/15/2026

Shredding the wrong document could cost you 💸

Most people apply one blanket rule to every financial document they own, and it works fine until it suddenly doesn't.

Before anything goes in the shredder, run through these three questions:

1. Is this tied to a tax return? The IRS standard window is 3 years from filing. But if income may have been underreported, that window stretches to 6 years. Never filed for that year? Keep it indefinitely.

2. Is this tied to an asset you still own, or sold recently? Property improvement records, investment purchase confirmations, inherited asset valuations — these need to stay until 3 years after you sell. Your cost basis lives in those documents.

3. Is this related to a Roth contribution or conversion? Form 8606 filings and Roth records belong in a permanent file. Their shelf life can stretch decades.

If a document answers no to all three? Utility bills, old pay stubs, bank statements older than a year — those can go, no guilt.

Thirty seconds per document, and the "but what if I need this" anxiety disappears.

If you're in the middle of a paper purge and want to talk through what your records situation actually looks like, book a Learn More Call: https://m.levitate.ai/c3829e-3m1p5f/Learn-More-Call

Privacy Policy and Disclosures/Terms of Use documents are linked in the website footer. Disclosures document URL: https://irp.cdn-website.com/0b5a1e75/files/uploaded/DISCLOSURES+-+TERMS+OF+USE+-+PURPOSEFUL+MONEY.pdf. Privacy Policy URL: https://irp.cdn-website.com/0b5a1e75/files/uploaded/Privacy-Policy-Updated.pdf. CFP® and Certified Financial Planner™ marks used with trademark symbols throughout.

Purposeful Money is a financial advisor serving Women in their 50s and beyond approaching or already in retirement.

October is National Financial Planning Month—a timely reminder to look beyond the numbers and make sure your retirement ...
10/13/2026

October is National Financial Planning Month—a timely reminder to look beyond the numbers and make sure your retirement plan still supports the life you want to live.

For women approaching or enjoying retirement, a year-end review can bring clarity around:
• Retirement income and investment strategy
• Tax planning, including required minimum distributions
• Social Security and Medicare decisions
• Estate and legacy planning
• The goals and priorities shaping your Season of You™

At Purposeful Money, I take a holistic, plain-English approach to retirement planning so you can move forward with greater confidence.

Ready for a thoughtful review of where you are and what comes next? Reach out to schedule a Learn More Call.

10/13/2026

Most women don't realize their 2026 income sets their 2028 Medicare premiums 👀

And if you cross the wrong threshold, you could be paying nearly $1,000 more per year in Medicare surcharges, before you've even filled a single prescription.

This is called IRMAA, and it catches a lot of smart, well-prepared women completely off guard in retirement.

Here's the good news: when you have a mix of traditional IRA, Roth, and taxable accounts, you actually have a choice about which bucket your income comes from each year.

That flexibility is the key to keeping your Medicare costs predictable and under control.

Roth conversions, strategic withdrawals, Social Security timing, and cash flow don't each live in their own silo. When they're coordinated together, your Medicare bill isn't a surprise. It's a number you planned years in advance.

If you're a woman in your 50s or early 60s starting to think about this, now is exactly the right time to look at the full picture.

Privacy Policy and Disclosures/Terms of Use documents are linked in the website footer. Disclosures document URL: https://irp.cdn-website.com/0b5a1e75/files/uploaded/DISCLOSURES+-+TERMS+OF+USE+-+PURPOSEFUL+MONEY.pdf. Privacy Policy URL: https://irp.cdn-website.com/0b5a1e75/files/uploaded/Privacy-Policy-Updated.pdf. CFP® and Certified Financial Planner™ marks used with trademark symbols throughout.

Purposeful Money is a financial advisor serving Women in their 50s and beyond approaching or already in retirement. Specific client markets include: Baby Boomers, Generation X, singles (widowed, divorced, never married). Clients generally have at least $1.5 million in investable assets or meet a $15,000 annual minimum fee. Married couples are also served, with both spouses included in the planning partnership.

National Savings Day is a helpful reminder that meaningful progress does not always start with a major financial change....
10/12/2026

National Savings Day is a helpful reminder that meaningful progress does not always start with a major financial change. Often, it begins with a few intentional decisions that support the retirement and life you want to create.

For women over 50, saving with purpose may mean reviewing retirement contributions, building flexibility into a retirement income plan, preparing for future taxes, or clarifying how today’s choices fit your next Season of You™.

Swipe for practical ways to make your savings habits more intentional.

If you would like a judgment-free conversation about holistic retirement planning, I am here to help. Purposeful Money serves clients in Naples and virtually nationwide.

10/08/2026

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Naples, FL
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