Retire With Ryan
In this episode, I’m helping you kick off 2026 by reflecting on financial habits that pave the way for a successful retirement. As we set our goals for the year ahead, I share the four key traits I’ve observed in successful retirees, drawn from years of experience working with people from all walks of life. You’ll hear practical advice on how to work hard and invest consistently, the importance of living within your means, and ways to avoid common investment pitfalls that can derail your progress. Whether you’re just starting your retirement planning or fine-tuning your financial...
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As we turn the calendar to 2026, I reveal my forecasts for the stock market, interest rates, and top asset classes, and take a look back at how my 2025 predictions stacked up against reality. From the S&P 500’s rollercoaster performance to the ongoing rivalry between growth and value stocks, and even a showdown between bitcoin and gold, I break down what the numbers were, where I hit the mark, and where I missed. You’ll also hear my insights on international versus U.S. stocks, the outlook for small caps, and what the Federal Reserve might do with interest rates in the year ahead. Get...
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2025 has been a year of significant highs and lows, a bittersweet time marked by personal loss but also tremendous growth in our community of listeners and clients. As we wrap up the year, I wanted to take a moment to reflect and, more importantly, to give back by answering the most pressing questions on your minds. In this episode, I’m tackling the top 10 most asked financial questions I received in 2025 from both clients and listeners. From the future solvency of Social Security and the reality of rising inflation to the specifics of Bitcoin and long-term care, we are covering the topics...
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529 college savings plans are a favorite tool for families looking to fund education, but recent updates have made them even more compelling. With the passing of the One Big Beautiful Tax Act in 2025, there have been some exciting changes to what you can use 529 funds for, including expanded coverage for K-12 tuition, test fees, vocational programs, and support for learning differences. I also discuss the various tax advantages of contributing to a 529 plan, like state tax deductions, tax-deferred growth, and even the ability to roll leftover funds into a Roth IRA for your child. He offers...
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In the season of giving, we’re discussing making charitable contributions in 2025 and 2026. Americans are known for their generous donations to worthy causes, but understanding the best ways to give and maximize your tax benefits is key. This episode covers four effective strategies for making charitable contributions, from utilizing Qualified Charitable Distributions (QCDs) from your retirement accounts to cash donations, gifting highly appreciated stock or real estate, and using donor-advised funds. I also break down recent and upcoming tax law changes that impact your ability to itemize...
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Healthcare planning is a huge part of getting ready for your retirement. In this episode, I tackle one of the most pressing updates for retirees: the latest changes to Medicare premiums for 2026, including important surcharges, deductibles, and strategies to help you manage your healthcare expenses. I’m helping you understand the significant increases in Medicare Part B premiums and deductibles, the impact these changes will have on your Social Security benefits, and why waiting to claim Social Security might pay off. Listen in to get helpful strategies for appealing IRMAA surcharges...
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As 2025 comes to a close, we’re here to help you make the most of year-end tax planning. I’m explaining seven actionable strategies to help you minimize your tax liability and optimize your retirement savings before the New Year. From maximizing retirement plan contributions and exploring Roth conversion opportunities to using donor-advised funds for charitable giving and getting the most from your health savings accounts, this episode is packed with practical advice. The insights I’m sharing in this episode will guide you through the essential moves you need to consider before...
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There are important changes coming to 401 (k), 403 (b), and 457 retirement plans in 2026, so I’m focusing on how these updates may impact catch-up contributions for individuals over age 50. With the Secure Act 2.0 on the horizon, higher earners will soon have to make their catch-up contributions as Roth (post-tax) rather than pre-tax contributions, potentially affecting their take-home pay and tax strategies. Tune in as I walk you through what you need to know, how to prepare for these new rules, and actionable steps to make the most of your retirement savings. You will want to hear...
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If you’ve spent any time on social media or read personal finance blogs, you’ve likely encountered a buzz around Roth IRAs and, specifically, Roth conversions. This week I’m discussing the details of Roth conversions, what they are, how they work, and why they’re crucial for those looking to optimize their retirement finances. Roth IRAs hold a special appeal: the promise of tax-free income in retirement. And most people would agree that having tax free income in retirement is preferable over having taxable income. Yet, for many people, especially those in their 50s and older, most of...
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Retirement planning is an ever-evolving process, and staying informed about changes to Social Security, Medicare, and tax limits is crucial to making the most of your golden years. On this episode of Retire with Ryan, I’m sharing important updates on the 2026 Social Security cost of living adjustment (COLA), projected changes to Medicare Part B premiums, and strategies for managing income in retirement. The newly announced cost-of-living adjustment (COLA) for 2026 will see benefit checks rise by 2.8%. I break down how the yearly adjustments are calculated, why they matter for seniors,...
info_outlineThe power of Health Savings Accounts (HSAs) as a tool for both managing health expenses and building your retirement savings is often overlooked.
On this episode, I’m sharing the basics of HSAs, highlighting their triple tax-free advantage, and explaining why they might be one of the best ways to maximize your retirement savings, even compared to more familiar accounts like IRAs and 401(k)s.
I also unpack some important upcoming changes to HSAs thanks to the One Big Beautiful Bill Act, set to take effect in 2026. These changes expand HSA eligibility, especially for those on healthcare exchange plans and direct primary care memberships.
Whether you’re new to HSAs or looking to fine-tune your retirement strategy, my practical tips—like how to track reimbursements, invest your HSA funds wisely, and ensure you’re making the most of every retirement planning opportunity.
You will want to hear this episode if you are interested in...
- [00:00] HSA contributions and eligible expenses.
- [03:33] HSA eligibility and individual plans.
- [07:27] HSA vs. 401(k) savings benefits.
- [12:10] HSAs and tax-free retirement reimbursements.
- [14:57] HSA contributions and Medicare Timing.
- [16:44] Top HSA provider tips.
What is an HSA and Who Qualifies?
Health Savings Accounts (HSAs) are often overlooked as powerful retirement planning vehicles. They are tax-advantaged accounts that allow individuals with high deductible health plans (HDHPs) to save and pay for qualified medical expenses.
To be eligible, you must be enrolled in a qualifying HDHP; not all plans make the cut, so check with your insurer or employer to confirm eligibility. For 2025, annual contribution limits are $4,300 for individuals and $8,550 for families, with an additional $1,000 catch-up allowed for those age 55 and over.
Both you and your employer can contribute, but the total combined contribution cannot exceed these limits.
Triple Tax Advantage: The Unique HSA Benefit
HSAs are the only accounts that offer a triple tax advantage:
- Pre-tax contributions: Contributions reduce your taxable income for the year, helping you save on federal and (in most cases) state income taxes.
- Tax-free growth: Money in your HSA can be invested, and all interest, dividends, and capital gains are tax-free while in the account.
- Tax-free withdrawals: Withdrawals used for qualified medical expenses remain tax-free, even in retirement.
This makes HSAs one of the most tax-efficient savings vehicles available.
HSAs as a Retirement Strategy
While the primary purpose of an HSA is to cover medical expenses, its value extends far beyond that, especially for forward-thinking retirement planners. Many people cover their current medical out-of-pocket expenses with regular cash flow, allowing their HSA investments to grow tax-free for years, even decades.
Upon reaching age 65, you are allowed to withdraw funds for non-medical expenses without penalty (although you will owe income tax, much like a traditional IRA). For medical expenses—including Medicare Part B, D, and Medicare Advantage premiums—withdrawals remain tax-free.
However, Medigap policy premiums are not eligible for tax-free reimbursement from your HSA. A strategic approach can involve tracking your unreimbursed eligible medical expenses over the years.
You can reimburse yourself in retirement with HSA funds for past qualified expenses, effectively turning your HSA into a tax-free retirement “bonus.”
New HSA Legislation on the Horizon
Looking ahead to 2026, recent legislative changes will further expand HSA eligibility and flexibility.
Expanded Access for Health Care Exchange Plans:
Before 2026, only certain HDHPs on the healthcare exchange allowed HSA contributions. The One Big Beautiful Bill Act will enable individuals enrolled in any Bronze-tier plan through the health care exchange to qualify for HSA contributions, potentially making over 7 million more people eligible.
Direct Primary Care Compatibility:
Membership in direct primary care plans—where patients pay a monthly fee for enhanced access to primary care services—will now be compatible with HSA eligibility, subject to fee limits ($150/month for individuals, $300/month for families, indexed to inflation). Previously, participating in such plans disqualified individuals from contributing to HSAs.
Common HSA Mistakes and Best Practices
Investing your HSA balance (beyond a buffer for immediate health costs) can help you harness the benefits of compound growth over time. Compare fees and investment options among HSA providers to maximize long-term gains.
Be mindful when approaching Medicare eligibility. HSA contributions must stop six months before you enroll in Medicare Part A, due to retroactive coverage.
Resources Mentioned
- Retirement Readiness Review
- Subscribe to the Retire with Ryan YouTube Channel
- Download my entire book for FREE
- IRS List of Covered HSA Expenses
Connect With Morrissey Wealth Management
www.MorrisseyWealthManagement.com/contact