4 Things All Successful Retirees Do, #287
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...
info_outline
6 Stock Market Predictions For 2026, #286
Retire With Ryan
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...
info_outline
Most Asked Financial Questions of 2025, #285
Retire With Ryan
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...
info_outline
Top 5 Tax Benefits of 529 Plans, #284
Retire With Ryan
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...
info_outline
4 Ways To Receive A Tax Deduction For Charitable Contributions in 2025 and 2026, #283
Retire With Ryan
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...
info_outline
2026 Medicare Part B Premium Surprises, #282
Retire With Ryan
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...
info_outline
7 Year End Tax Moves For Pre-Retirees in 2025, #281
Retire With Ryan
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...
info_outline
Major Changes Coming To 401K, 403B, and 457 Retirement Plans in 2026, #280
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...
info_outline
Mapping Out A Plan For Roth Conversions, #279
Retire With Ryan
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...
info_outline
Social Security 2026 Cost Of Living Update, #278
Retire With Ryan
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_outlineRetirement 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, and the impact of inflation on Social Security. I also discuss the expected jump in Medicare Part B premiums, what IRMAA means for higher-income retirees, and important changes to the Social Security wage base and retirement earnings limits.
Whether you're thinking about when to start your benefits or you want to strategize your retirement income, this episode will give you practical tips and resources to help you make the most of your retirement planning.
You will want to hear this episode if you are interested in...
- [00:00] Social Security cost-of-living adjustment (COLA).
- [02:54] COLA trends and historical adjustments.
- [04:48] Social Security benefit updates.
- [10:56] Social Security earnings limit explained.
- [11:56] Social Security and Medicare updates.
What to Expect from Social Security COLA for 2026
After a brief delay caused by a government shutdown, the Social Security Administration (SSA) announced that benefit checks will rise by 2.8% beginning January 2026. This increase is slightly higher than last year’s 2.5% and a bit less than the 2024 bump of 3.2%. While not the largest adjustment in history, any increase helps seniors keep pace with the rising costs of essentials like groceries, taxes, and insurance.
How is COLA Calculated?
SSA bases COLA changes on the Consumer Price Index for Urban Wage Earners and Clerical Workers (CPI-W), specifically by comparing the average index for each month in the third quarter of one year to the same period in the previous year. Since 1972, this approach has pegged benefit adjustments to actual inflation, providing a more predictable and timely increase for beneficiaries. Beneficiaries will receive details about their new benefit amounts in early December.
Medicare Part B Premiums
The base premium for Medicare Part B is predicted to rise from $185 to approximately $206.50 per month in 2026, a significant increase of roughly 11.6%. Final figures will be released later, but even preliminary estimates suggest a noticeable impact, especially for fixed-income retirees.
Income Related Monthly Adjustment Amount (IRMAA) may add further costs to your Medicare premiums if your income exceeds certain thresholds. For 2026, your IRMAA status will be determined by your 2024 tax return, due to a two-year lag in income reporting. Higher earners could see premiums up to $443.90 per month, so it’s critical to strategize IRA distributions and capital gains to avoid unnecessary surcharges.
If your financial situation changes, such as a recent retirement, you may appeal IRMAA charges using Form SSA-44. Ryan Morrissey recommends reviewing prior episodes and his blog for more on appealing IRMAA.
Social Security Taxes and Retirement Income Limits
The maximum wage base for Social Security taxes will jump to $184,500 in 2026 (up from $176,100), meaning any income above this threshold won’t be subject to Social Security tax.
Retirees collecting Social Security before full retirement age must monitor their earned income. For 2026, the limit rises to $24,480. Earnings above this cut-off will reduce your Social Security benefit by $1 for every $2 earned. Once you reach your full retirement year, the earnings limit increases sharply to $65,160, and after your birthday, there’s no limit.
The latest updates to Social Security and Medicare reflect ongoing efforts to help retirees keep pace with inflation and evolving economic conditions. Successful retirement isn’t just about knowing the numbers, it’s about strategizing your income to minimize taxes, avoid excess premiums, and maximize your benefits.
Resources Mentioned
- Retirement Readiness Review
- Subscribe to the Retire with Ryan YouTube Channel
- Download my entire book for FREE
Connect With Morrissey Wealth Management
www.MorrisseyWealthManagement.com/contact