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Retire With Ryan

Retire With Ryan

By: Ryan R Morrissey
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Summary

 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 Economics Personal Finance
Episodes
  • The Unforeseen Costs of Aging In Place, #303

    The Unforeseen Costs of Aging In Place, #303
    Apr 28 2026
    For many Americans, the idea of aging in place, or remaining in your own home as you grow older, represents comfort, independence, and familiarity. Most people understand the emotional benefits of remaining in a familiar environment, but often overlook the financial challenges, from home modifications and repairs to healthcare and in-home support, that could threaten their retirement savings. On the show this week, I break down the five key areas where your budget could take a hit and offer strategies to help you plan ahead, evaluate your options, and secure your ideal retirement lifestyle. If you're thinking about your future living situation or helping a loved one prepare, you won't want to miss this episode. You will want to hear this episode if you are interested in... [00:00] The preference for aging in place [05:08] Home modifications for accessibility [08:28] Considering home maintenance and healthcare costs [13:32] Planning housing costs for retirement [14:55] Planning for future housing needs Understanding Aging in Place The reasons people want to age in place are clear: minimal upheaval, a sense of control, independence, and the emotional security of familiar surroundings. But it's common to underestimate what it actually costs to make this dream a reality. Many retirees fail to plan for the inevitable expenses, which can erode savings and force uncomfortable, last-minute decisions down the road. Five Major Financial Considerations for Aging in Place 1. Home Modifications A key prerequisite for staying at home safely is making your living space accessible. While some modifications—like installing grab bars or lever handles—may be relatively inexpensive, needs can escalate quickly. More significant updates, such as walk-in tubs, stairlifts, or ramp additions, can run into the tens of thousands of dollars. Even a basic stairlift installation can cost over $5,000, and major renovations like adding a first-floor bedroom or bathroom can easily be prohibitive, especially if done reactively in a crisis. 2. Maintenance and Repairs Beyond mortgage payments, insurance, and property taxes, ongoing home maintenance is a substantial, often underestimated expense. Homes age just as their residents do, meaning roofs (with a typical 25-30-year lifespan), HVAC systems (lasting 10-15 years), and even electrical or plumbing systems may require expensive repairs. Consider getting a thorough evaluation of your home's current state and expected major repairs over the coming decades. Add these projected costs into your retirement budget so they don't catch you off guard. 3. Upkeep and Outsourcing Chores When you first retire, you may be able to mow the lawn, shovel snow, or clean gutters. But as you age, these tasks may become physically challenging, if not unsafe, necessitating the hiring of help. The annual cost of landscaping, snow removal, and routine upkeep can add up, sometimes exceeding the maintenance fees of a condominium or senior community. Evaluate the true costs of outsourcing these chores over the long haul. In some cases, a housing alternative with built-in maintenance can be both safer and more cost-effective. 4. Medical and Healthcare Needs Aging at home often means additional out-of-pocket expenses for home healthcare aides, nurses, and various medical equipment. Many necessities, such as medical alert systems or even prescription medication management solutions, are not fully covered by Medicare or standard insurance. It's essential to factor in potential costs for in-home care, equipment, and transportation to appointments should you lose the ability to drive. 5. Long-Term Care and Support A frequent misconception is that Medicare will cover most long-term or in-home care needs. In reality, this type of care—particularly ongoing daily care—typically isn't covered, aside from certain short-term situations. Long-term care insurance is an option, but only a small percentage of Americans over 50 have it, often due to high premium costs. Given that full-time nursing care can cost as much as $180,000 annually in some regions, having a clear strategy for funding care, whether through insurance, earmarked savings, or asset liquidation, is critical. Developing a Proactive Aging in Place Plan To successfully age in place, start planning early. Assess your home's lifespan and the modifications needed, estimate maintenance and care costs, and integrate these projections into your retirement strategy. If the total costs seem unmanageable, now is the time to explore alternatives like downsizing, moving to a condominium, or relocating to a community with built-in support, especially in today's favorable seller's market. Making these plans before a crisis ensures you'll have more options, less stress, and a better chance at maintaining both your independence and your financial security throughout retirement. Resources Mentioned Retirement Readiness Review ...
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    16 mins
  • How Collecting Social Security Early Can Impact Your Affordable Care Act Subsidy #302

    How Collecting Social Security Early Can Impact Your Affordable Care Act Subsidy #302
    Apr 21 2026
    For many Americans approaching retirement, financial planning means more than just maximizing savings and deciding when to claim Social Security. If you're not yet eligible for Medicare and rely on health coverage through the Affordable Care Act (ACA), your Social Security claiming decision at age 62 could have a dramatic effect on your insurance costs. On the show this week, I explore the nuances of how your income, and especially the timing of your Social Security benefits, can impact your eligibility for ACA premium tax credits—and what you can do to avoid costly surprises. You will want to hear this episode if you are interested in... [00:00] Retirement income and tax planning [03:35] Understanding ACA tax credits [07:44] Managing income for ACA tax credits [10:38] Social Security and tax calculations [14:57] Strategies for tax-free income access Are ACA Premium Tax Credits, and Why Do They Matter? Premium tax credits, often referred to as ACA subsidies, are financial incentives designed to make health insurance more affordable for individuals and families who purchase coverage through healthcare.gov or a state exchange. These credits are contingent on your income, specifically your household's Modified Adjusted Gross Income (MAGI). For 2026, a single person can qualify for ACA subsidies if their MAGI is between 100% and 400% of the federal poverty level (FPL)—$62,600 in 2026 for an individual, and $84,600 for a couple. If you earn even $1 above this ceiling, you lose your entire premium subsidy—a phenomenon known as the "subsidy cliff". With millions of Americans currently receiving subsidies, understanding how your retirement income decisions could threaten this benefit is essential for sound financial planning. How Income Is Calculated for ACA Subsidies Not all income is created equal when it comes to ACA subsidies. The government uses your MAGI, which is your Adjusted Gross Income (AGI)—the number found on your tax return—plus certain items like tax-exempt bond interest and non-taxable Social Security benefits. This includes: Wages and self-employment income Social Security benefits (both taxable and non-taxable portions) Retirement account distributions (except Roth IRAs or Roth 401ks) Rental, interest, and dividend income Capital gains Additionally, some deductions, like contributions to IRAs, HSAs, and student loan interest, can reduce your AGI, and thereby your MAGI, giving you potential tools for staying below the subsidy cliff. The Social Security Timing Dilemma Collecting Social Security early at age 62 may sound appealing, but it comes with strings attached for ACA recipients. A critical point is that not all of your Social Security benefits are necessarily taxable. However, when calculating MAGI for ACA purposes, you must add back even the non-taxable portion, which can push your income above the subsidy threshold. For example, if you take a modest IRA distribution and also begin Social Security, the cumulative MAGI could surprise you. Strategies to Preserve Your ACA Subsidy Given the high stakes, careful income planning is essential for anyone under 65 not covered by Medicare and receiving an ACA subsidy. You could delay Social Security, as waiting to claim benefits may help keep your income lower. You could also draw from Roth accounts or savings, withdrawals from Roth IRAs or 401(k)s—provided they're qualified—don't count as income. Likewise, using savings or HSA reimbursements has no impact on MAGI. IRA, HSA, and 401(k) contributions can reduce your MAGI, especially if you miscalculated and need to lower your income late in the year. The most important thing to do is plan withdrawals: Time your IRA or 401(k) distributions and capital gains so they don't coincide with years when you're dependent on ACA subsidies. Avoiding the "Subsidy Cliff" Surprise Perhaps the most important lesson is to monitor your income projections carefully throughout the year and to report your expected MAGI precisely when applying for coverage. Exceeding the threshold by even a small amount can cause you to lose your subsidy, resulting in thousands of dollars in unexpected premium costs come tax time. Retirement planning requires a big-picture approach that balances income sources, tax implications, and healthcare costs. If you're considering Social Security at 62 and not yet on Medicare, pay close attention to how your income choices will affect your ACA subsidy—because when it comes to the "subsidy cliff," every dollar counts. Resources Mentioned Retirement Readiness Review Subscribe to the Retire with Ryan YouTube Channel Download my entire book for FREE Episode 267: Surviving the ACA Subsidy Cliff Connect With Morrissey Wealth Management www.MorrisseyWealthManagement.com/contact Subscribe to Retire With Ryan
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    17 mins
  • How To Avoid The Pain of Estimated Tax Payments in Retirement #301

    How To Avoid The Pain of Estimated Tax Payments in Retirement #301
    Apr 14 2026
    As April 15 approaches, marking the end of the 2025 tax filing season, many filers are facing an unpleasant surprise: tax penalties are rising, especially for those who miss timely payments or underestimate their quarterly taxes. In this episode, I'm taking you through the reasons behind the recent surge in tax penalties and highlighting how retirees, the self-employed, and investors are increasingly affected. I'll also break down the key rules, safe harbor provisions, and practical steps you can take to avoid underpayment penalties. You will want to hear this episode if you are interested in... [00:00] Quarterly taxes and penalties explained [01:38] Why has there been an increase in tax penalties? [03:10] Retirees are at risk of underpayment penalties [04:28] Penalty rate increase details [06:15] Safe harbor for quarterly taxes [07:38] Key deadlines for estimated tax payments [08:33] Smart strategies to avoid penalties The Surge in Tax Penalties: What's Happening? Recent data shows a dramatic increase in tax penalties, particularly for those earning between $200,000 and $500,000. In fact, filers in this bracket were hit with about $1.3 billion in penalties in 2024—triple the amount compared to 2021, with the number of affected individuals increasing by 30% to almost 3 million. This uptick is fueled by both higher penalty rates and a widespread lack of awareness of changes in tax law. The penalty rates themselves have more than doubled: while underpayment penalties hovered at 3% in 2021, they peaked at 7% before moderating to 6% as of April 2026. Unfortunately, many taxpayers simply aren't aware these penalties exist until it's too late. Why Are Retirees at Risk? Traditionally, underpayment penalties were most common among the self-employed. Retirees are now increasingly affected due to the nature of their income sources. Most employees have income taxes withheld automatically from each paycheck, satisfying IRS requirements to pay taxes "on time". But retirees, relying on retirement account withdrawals, Social Security, and investments, often experience income without automatic withholding, leaving them vulnerable to quarterly underpayment rules. For example, someone who sells investments or performs Roth conversions in retirement may realize sizable gains in a single quarter. If taxes aren't paid promptly on those gains, penalties can accrue for each quarter the IRS deems underpaid. Understanding Quarterly Estimated Taxes and Safe Harbors The IRS requires all filers who expect to owe $1,000 or more in taxes to pay at least 90% of their total tax bill by the filing deadline. This can be accomplished through either withholding, estimated payments, or a combination of both. There are four key deadlines for estimated tax payments: April 15, June 15, September 15, and January 15 (05:45). Those with irregular or lumpy income—common among retirees taking periodic distributions—must still divide payments evenly across these dates, unless they opt to track payments and income month-by-month using IRS Schedule AI. Another way to avoid penalties is by meeting the "safe harbor" thresholds. For those with income under $150,000, paying 100% of the prior year's tax usually suffices; for incomes above $150,000, 110% of the previous year's liability is required. Importantly, these amounts must also be paid in equal quarterly installments, not just as a lump sum at year's end. Practical Strategies to Avoid Penalties These are the strategies I recommend for retirees and investors: Review Income: Sit down with your accountant or financial advisor to project total income from retirement accounts, Social Security, pensions, and investments. Adjust Withholding: If possible, increase tax withholding on retirement distributions to mimic regular paycheck withholding and satisfy quarterly obligations. Make Timely Payments: If you do need to make estimated payments, ensure they're made electronically or by check before each deadline. The IRS requires extra steps for online payments, so plan ahead. Use Schedule AI or Form 2210: If your income is highly variable—such as a large Roth conversion late in the year—use Schedule AI to clarify when the income was received. This can prevent penalties from being calculated as if you earned evenly throughout the year. Penalty Waivers: If you recently retired or became disabled, IRS waivers may apply. File Form 2210 to request relief. Tax penalties are increasingly common, especially among retirees with diverse income sources. By planning and using the IRS's safe harbor rules and payment deadlines, you can avoid these costly surprises. Resources Mentioned Retirement Readiness Review Subscribe to the Retire with Ryan YouTube Channel Download my entire book for FREE Form 2210 Connect With Morrissey Wealth Management www.MorrisseyWealthManagement.com/contact Subscribe to Retire With Ryan
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    11 mins
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