Retire With Ryan
Medicare open enrollment is here, running from October 15th to December 7th, and it's especially important for those who rely on Medicare. Plans change each year—and so may your needs. Not reviewing your Medicare coverage could leave you exposed to unexpected costs or disrupt your access to preferred doctors and medications. On this week's show, I explore five key steps to help ensure you get the right coverage for 2027. You will want to hear this episode if you are interested in... [01:40] Reviewing Medicare coverage for 2027 [02:49] How to check provider status: annual notice of...
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For those actively planning for a secure retirement, smart tax planning is essential—especially as 2026 comes to a close. Tax laws and contribution limits keep evolving, and timely adjustments can help you keep more of your hard-earned money. On the show this week, I share seven critical tax strategies that can boost your retirement savings while minimizing your tax liability. Here’s a deeper look at each move and how to integrate it into your financial plan. You will want to hear this episode if you are interested in... [01:41] Maxing out pre-tax retirement plans [04:32] Making...
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I break down the upcoming Social Security cost-of-living adjustment (COLA) for 2027, share my predictions on the new numbers, and explain what you should do to prepare. With inflation still affecting retirees, I explain how the COLA is calculated, what it means for your benefits, and the factors that could affect your retirement income next year. This episode has essential tips to help you make the most of the upcoming increases and manage your retirement finances confidently. You will want to hear this episode if you are interested in... [01:10] projected 2027 COLA estimates ...
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What should you do if the stock market crashes right after you retire? In this episode, I discuss what happens if you experience a major market decline in your early retirement years, explain the concept of sequence of return risk, and share a few strategies to safeguard your hard-earned nest egg and maintain peace of mind. You will want to hear this episode if you are interested in... [01:20] What to do if the stock market crashes right after retiring [04:09] Sequence of return risk explained [07:14] Preparing for market declines in retirement [13:43] Tax strategies during market...
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How much have you thought about Health Savings Accounts (HSAs) and what happens to them once you enroll in Medicare? Whether you’re nearing age 65, wondering if you can keep contributing to your HSA, or curious about how you can use your HSA funds in retirement, this episode covers it all. I explain the rules around HSA contributions after enrolling in Medicare, the types of medical expenses you can pay for tax-free, and what happens to your HSA if there’s still money in it after you pass away. You will want to hear this episode if you are interested in... [01:51]...
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As you transition into retirement, tax planning might not be at the top of your to-do list—but overlooking it can lead to costly mistakes. This week, I break down the five biggest tax pitfalls new retirees face, from unexpected taxes on Social Security benefits to costly Medicare premium surcharges and missed Roth conversion opportunities. I’m also sharing a few of my favorite strategies to avoid unnecessary state taxes and manage your retirement distributions with confidence. You will want to hear this episode if you are interested in... [01:45] Without planning, your risk...
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Roth IRAs are a powerful retirement tool, much loved for their promise of tax-free growth and withdrawals. But embedded in the rules for Roth IRAs are two little-understood 5-year rules. Misunderstanding these can trip up even savvy savers, potentially exposing your hard-earned gains to taxes and early withdrawal penalties. This week I’m giving you an expert breakdown to clarify how the rule works and bust some common misconceptions. You will want to hear this episode if you are interested in... [01:13] Tax-deferred growth and conditions for tax-free distributions [05:39] Taxes...
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Long-term care coverage is an essential, yet often misunderstood, aspect of retirement planning in the United States. Although many people will require some form of long-term care as they age, most are unprepared for the high costs and limited coverage options available. On the show this week, I’m debunking common myths like the notion that Medicare will fully cover all long-term care costs and taking a deep dive into the four main ways retirees can pay for these expenses. You will want to hear this episode if you are interested in... 00:00 Understanding the options for...
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On the show this week, I’m helping you understand why bond prices have been dropping, what actions investors should take, and whether bonds still have a place in a retirement portfolio. I discuss the different types of bonds and how interest rates impact bond prices. I also dig into the importance of maintaining a diversified portfolio and the role bonds can play in reducing overall volatility during retirement. You will want to hear this episode if you are interested in... [02:03] Types of Bonds and issuers [03:21] Risks of investing in junk bonds [04:39] Why have bond prices...
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Retirement is often imagined as the reward after decades of hard work—a time for travel, relaxation, and quality time with loved ones. But for many Americans, the anxiety of running out of money casts a long shadow over these golden years. Studies reveal that concerns about outliving savings are more prevalent than fears of dying prematurely. This week we’re discussing the five key reasons retirees run out of money and sharing practical steps you can take to secure your financial future. You will want to hear this episode if you are interested in... [02:16] Even high-income...
info_outlineI break down the upcoming Social Security cost-of-living adjustment (COLA) for 2027, share my predictions on the new numbers, and explain what you should do to prepare. With inflation still affecting retirees, I explain how the COLA is calculated, what it means for your benefits, and the factors that could affect your retirement income next year. This episode has essential tips to help you make the most of the upcoming increases and manage your retirement finances confidently.
You will want to hear this episode if you are interested in...
- [01:10] projected 2027 COLA estimates
- [03:15] Average COLA increases over recent periods
- [04:20] How COLA is applied to current and future beneficiaries’ benefits
- [06:24] Expected increase in IRMAA (Income-Related Medicare Monthly Adjustment Amount), its brackets, and projected changes to income thresholds
- [08:30] Impact for high earners once the wage base is exceeded
- [09:29] Changes to the earnings test amounts for those reaching full retirement age
What is the Projected 2027 Social Security Cost of Living Adjustment?
Next week, the Social Security Administration will release the official 2027 COLA. Early estimates put this increase between 3.5% and 3.7%. If the actual figure lands at 3.3% or higher, it will mark the largest single-year raise since 2003. For perspective, the COLA was 2.8% in 2026 and 2.5% in 2025. Over the past five years, retirees have seen a cumulative benefit increase of about 23%, largely spurred by post-pandemic inflation.
Why is this important? Because rising prices on essentials, groceries, gas, heating oil, property taxes, and homeowners insurance continue to challenge retirees’ budgets. The COLA helps Social Security benefits keep pace with these increases, though it’s not always a perfect match.
How Social Security Calculates COLA
Since 1972, Social Security COLAs have been determined using the Consumer Price Index for Urban Wage Earners and Clerical Workers (CPI-W), focusing on the average CPI-W during July, August, and September, compared from one year to the next. Before this system, Congress had to approve benefit increases—a process fraught with political uncertainty.
Inflation’s ebb and flow have shaped COLA history. While the “3% rule” from the 1970s required at least a 3% CPI-W increase, Congress removed that threshold in 1986. Now, even a 0.1% change will trigger a benefit adjustment. Standout years include 1980 and 1981, with double-digit increases amid soaring inflation.
What Retirees (and Future Retirees) Should Do
The good news for most is that no action is needed to receive the new COLA. Social Security beneficiaries will be notified by mail in early December with their exact increase or can check their Social Security account online for quicker updates. The adjustment applies to gross benefit amounts—before tax withholding and Medicare premium reductions.
For those not yet claiming Social Security (age 62 and under), the COLA is still factored into your eventual benefit. When you do start collecting, your “primary insurance amount” will reflect these cumulative annual increases, thanks to Social Security’s method of indexing past wages into current dollars.
Medicare Premiums and IRMAA
A higher COLA is generally good news but is often offset by rising Medicare Part B premiums. For 2026, the base premium is $202.90 per month, with estimates suggesting a climb to $209.50 in 2027—a 3.4% increase. If your Social Security grows more than your Medicare premium rises, you’ll see a net gain, but not always by much.
Those with higher incomes may also face the Income-Related Monthly Adjustment Amount (IRMAA), which can tack on an additional $81.10 to $487 per month, depending on your reported income. These surcharges are based on tax returns from two years prior, making proactive tax planning essential.
Wage Base and Earnings Limits
The Social Security wage base—the maximum income subject to payroll tax—will likely rise to about $190,200 in 2027. Once you surpass this amount in earnings, you no longer pay Social Security tax for the year, which could be a small silver lining for high earners.
For those considering early Social Security, remember the earnings test limit: if you collect benefits before full retirement age and your work income exceeds $24,280 (projected to rise by around 3%), your benefits will be reduced. However, after reaching full retirement age (typically 67), these limits disappear.
Resources Mentioned
- Retirement Readiness Review
- Subscribe to the Retire with Ryan YouTube Channel
- Download my entire book for FREE
- Social Security Administration
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