Retire With Ryan
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,...
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With the term “financial advisor” being used so broadly these days, it’s harder than ever for retirees and investors to make sense of who’s actually guaranteed to act in their best interest. So let’s talk about the key responsibilities of fiduciaries, explore the differences between fee-only advisors and those who earn commissions, and go through why full disclosure and ongoing advice matter so much in your financial planning relationship. I share practical tips on how to vet potential advisors, whether you’re unhappy with your current one or searching for the right fit for the...
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Every year, Medicare Open Enrollment presents an important opportunity for retirees and individuals enrolled in Medicare to review, update, and make changes to their health and prescription drug coverage. If you’re on Medicare or approaching retirement, understanding the enrollment period and your options is crucial to ensuring comprehensive and cost-effective health care. I’m sharing the seven essential things you need to know to make the most of this important window. Whether you’re already enrolled in Medicare or want to stay ahead of your retirement planning, I explain key dates,...
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This episode is essential listening for anyone who’s inherited an IRA, especially in light of the game-changing SECURE Act. If you’ve inherited a retirement account from a non-spouse since 2020, this episode is packed with details you need to know to avoid unexpected tax bills and penalties. I explain the new rules for inherited IRAs, explaining the requirements and options for non-designated, non-eligible, and eligible designated beneficiaries. Whether you’re figuring out minimum distributions or seeking smart tax-planning strategies, you’ll get clear guidance on how these updates...
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You might have seen those viral articles promising a mysterious multi-thousand-dollar Social Security “bonus,” but are they actually legit? On the show this week, I separate fact from fiction, debunking the myths and sharing seven actionable strategies to help you get the most out of your Social Security over your lifetime. Whether you’re curious about how working longer, delaying your benefits, checking your earnings record, or understanding tax implications can impact your retirement paycheck, this episode is packed with valuable tips to help you make sure you’re not leaving...
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The Social Security Fairness Act, which was signed into law at the start of 2025, has been in effect for about nine months since this game-changing legislation repealed both the Windfall Elimination Provision and the Government Pension Offset, restoring and increasing Social Security benefits for millions of retirees, especially teachers and public employees who worked in jobs exempt from Social Security. In this episode, I discuss exactly who qualifies for these newly restored benefits, explain how the Social Security Administration is handling the rollout, and give you a step-by-step guide...
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It’s one of the most frequently asked questions by my clients as they prepare for retirement. And while a million dollars may sound like a lot, the reality is a bit more complex. There are several key factors to consider when planning your retirement, including factoring in taxes, evaluating withdrawal strategies, and understanding the cost of living where you plan to retire. Let’s break down how you can determine whether your nest egg will support your ideal retirement. You will want to hear this episode if you are interested in... [01:57] Evaluating if a million dollars is enough to...
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Are you turning 65 soon or starting to think seriously about healthcare in retirement? This week, I discuss the complicated world of Medicare—with a focus on the seven most costly mistakes people make when enrolling. From missing crucial deadlines and underestimating penalties, to overlooking the true costs Medicare doesn’t cover and getting tripped up by income-related surcharges, I give practical advice to help you avoid expensive pitfalls and make confident choices for your health and your wallet. Whether you’re working past 65, exploring Medicare Advantage and Medigap, or just...
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