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Retire With Ryan

Retire With Ryan

Di: Ryan R Morrissey
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If you're 55 and older and thinking about retirement, then this is the only retirement podcast you need. From tax planning to managing your investment portfolio, we cover the issues you should be thinking about as you develop your financial plan for retirement. Your host, Ryan Morrissey, is a Fee-Only CERTIFIED FINANCIAL PLANNER TM who lives and breathes retirement planning. He'll be bringing you stories and real life examples of how to set yourself up for a successful retirement.2020 Retirewithryan.com. All Rights Reserved Economia Finanza personale
Episodi
  • Social Security 2027 COLA Update, #326

    Social Security 2027 COLA Update, #326
    Oct 6 2026
    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 [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 ReviewSubscribe to the Retire with Ryan YouTube ChannelDownload my entire book for FREE Social Security Administration Connect With Morrissey Wealth Management www.MorrisseyWealthManagement.com/contact Subscribe to Retire With Ryan
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    11 min
  • Year-End Tax Moves For Pre-Retirees To Consider in 2026, #327

    Year-End Tax Moves For Pre-Retirees To Consider in 2026, #327
    Oct 13 2026
    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 after-tax contributions to retirement plans[06:05] In-plan Roth conversion and in-service distribution[09:54] Bunching charitable contributions using a donor-advised fund[10:40] Contributing to 529 plans for state tax deductions[12:24] Setting up a flexible spending account[13:16] Maximizing health savings account contributions[14:50] Year-end deadlines for tax strategies 1. Max Out Pre-Tax Retirement Contributions One of the most effective ways to reduce your taxable income is to contribute the maximum allowable amount to pre-tax retirement accounts like 401(k), 457, 403(b), or SIMPLE IRA plans. Contribution limits are different based on age and plan type—for example, individuals over 50 can contribute up to $32,500 to certain plans in 2026, while those under 50 are capped at $24,500. If you're between 60 and 63, look for special catch-up provisions that allow even higher contributions, up to $35,750 in some cases. Keep in mind that if your income exceeds $150,000 in 2025, portions of your catch-up contributions may have to be made as Roth contributions, meaning they won't reduce your taxable income but instead provide tax-free growth. 2. Consider After-Tax Contributions for Even Greater Savings Many employer-sponsored plans now allow for after-tax contributions beyond the standard limits. The combined contribution ceiling (including employer matches and profit sharing) can reach as high as $80,000 for those over 50. These after-tax contributions aren't deductible in the year you make them, but they set the stage for powerful strategies like the "mega backdoor Roth IRA," which can let you move larger sums into a Roth account for tax-free compounding growth. 3. Use Roth Conversions—Both In-Plan and Beyond If your plan allows it, consider converting after-tax contributions to Roth dollars through an in-plan Roth conversion. This lets future growth happen in the Roth portion, making withdrawals tax-free later. Under certain conditions (like reaching age 59½), you might also have the option to roll out your after-tax funds for a more favorable tax outcome 08:11. Doing the math on current and future tax brackets can help determine if a broader Roth conversion is advantageous—particularly in a year where your income is temporarily lower. 4. Leverage Donor-Advised Funds for Charitable Giving If you make regular charitable contributions yet rarely itemize deductions, a donor-advised fund can be a game changer. By "bunching" multiple years of giving into a single tax year through one of these funds, you may cross the threshold to itemize and get a larger tax deduction. You retain the flexibility to distribute to charities at your own pace in subsequent years. 5. Tap the Power of 529 Savings Plans for Education Expenses For those with college-bound children, contributions to a 529 plan can lead to valuable state tax deductions or credits. While some states limit deductions to their own plans, nine states allow contributions to any 529 plan to qualify. For example, in Connecticut, individuals can deduct up to $5,000 and couples up to $10,000 from their state income taxes when contributing. This can add up to hundreds of dollars in annual savings, especially when those funds were already earmarked for tuition. 6. Take Advantage of Flexible Spending Accounts (FSAs) If you're not enrolled in a high-deductible health plan but still incur significant out-of-pocket health costs, check if your employer offers a Flexible Spending Account. With a $3,400 per-person limit, couples can shield up to $6,800 of medical expenses from taxes each year. Be mindful of the "use-or-lose" rule—funds must be spent within a short time frame or risk forfeiture. 7. Max Out Health Savings Accounts (HSAs) with High-Deductible Plans For those on high-deductible health plans, HSAs offer triple tax advantages: contributions are tax-deductible, growth is tax-free, and qualified withdrawals are untaxed. Unused balances roll over indefinitely and can eventually be used for non-medical expenses in retirement with standard tax treatment, effectively functioning as another retirement account. Get a Head Start for Year-End Deadlines Many of these strategies require action before the end of the calendar year. By incorporating the appropriate tax moves, you can take control of your retirement planning and optimize ...
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    16 min
  • What Happens To My HSA When I Enroll In Medicare? #324

    What Happens To My HSA When I Enroll In Medicare? #324
    Sep 22 2026
    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] Ineligibility to contribute to HSAs after enrolling in any part of Medicare [03:02] When to stop HSA contributions[05:46] Automatic Medicare enrollment when collecting Social Security or some retirement benefits [08:00] Contrast between using IRA vs HSA to pay medical expenses [09:39] Using HSA for family expenses[14:27] Using the HSA post-65 for medical or other expenses What Changes With Medicare? One of the most important things to keep in mind is that once you enroll in any part of Medicare, you are no longer eligible to make HSA contributions. Continuing to contribute after enrolling in Medicare results in excess contributions, which are subject to a 6% excise tax each year the excess remains in the account. This penalty also applies to any income generated by those excess contributions, so immediate corrective action is necessary if you find yourself in this situation. Importantly, Medicare Part A coverage can be retroactive for up to six months if you delay enrollment. Because of this, it's recommended to stop contributing to your HSA at least six months before signing up for Medicare to avoid accidental over-contributions. Letting your employer know and possibly switching away from a high-deductible health plan before enrolling in Medicare can help prevent mistakes. Can You Still Contribute If You're Working Past 65? Some individuals continue working beyond age 65 and may wonder if they can keep adding to their HSA. The answer depends on two main factors: your (or your spouse's) participation in a qualified employer-sponsored health plan, and whether you are receiving Social Security or railroad retirement benefits. If you're still working and covered by a group plan with at least 20 employees, you can delay Medicare enrollment and keep contributing to your HSA. However, as soon as you start receiving Social Security or railroad benefits, you're automatically enrolled in Medicare Part A, meaning you must halt HSA contributions—even if you're still working. Carefully timing your Social Security enrollment can help maximize your HSA benefits. Making Tax-Free Withdrawals: Qualified Expenses After 65 Once you turn 65, your HSA is yours for life, even though contributions must stop. Withdrawals for qualified medical expenses remain tax-free—these include doctor's visits, prescription drugs, dental and vision care, hospital stays, Medicare Part B, Part D, and Medicare Advantage premiums, but not Medigap premiums. For example, if you and your spouse spend $500 monthly on Medicare premiums, you could take $6,000 out of your HSA tax-free each year. Long-term care costs, including insurance premiums and care expenses, can also be paid with HSA funds within certain annual limits based on your age. These limits increase with age, reaching $6,200 per year for those 71 and older as of 2026. What Happens to Your HSA After You Die? Upon death, if your spouse is the named beneficiary of your HSA, the account simply becomes theirs—with all tax advantages preserved. For any other named beneficiary, the HSA must be cashed in and its balance treated as ordinary income, losing its tax-preferred status. If no beneficiary is named, the HSA passes to your estate, triggering potentially higher taxes and delays in distribution. Resources Mentioned Retirement Readiness ReviewSubscribe to the Retire with Ryan YouTube ChannelDownload my entire book for FREE Connect With Morrissey Wealth Management www.MorrisseyWealthManagement.com/contact Subscribe to Retire With Ryan
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    16 min
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