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
  • Is The Social Security Lump Sum A Good Deal? #300

    Is The Social Security Lump Sum A Good Deal? #300
    Apr 7 2026

    On this milestone 300th episode of the Retire with Ryan podcast, I dig into whether the Social Security lump sum payment option is right for you. After a client reached out with questions about whether accepting a lump sum is a good deal, I want to break down how the option works, who it's available to, and the key factors to consider when making this important decision. If you're approaching retirement, this episode offers practical guidance on weighing the lump sum versus higher monthly benefits, health considerations, and the impact on survivor benefits and taxes.

    You will want to hear this episode if you are interested in...

    • [00:00] Getting started with Social Security

    • [05:22] monthly Social Security benefit calculations

    • [06:11] Reasons to take the lump sum

    • [07:48] Health concerns and social security benefits

    • [08:27] When passing on the lump sum is a better choice

    • [10:24] Your lump sum may increase your taxable income

    Should You Take the Social Security Lump Sum?

    When you apply for Social Security after your full retirement age (FRA), the Social Security Administration may offer a lump sum payment. This option is generally given to individuals who delay collecting benefits past their FRA. The lump sum typically covers up to six months of retroactive benefits.

    For example, if your FRA is 66 and you apply a year later, you might be eligible for a lump sum equal to six months of prior payments. However, there's a catch: your monthly benefit will be calculated as if you started receiving Social Security six months earlier, resulting in a lower monthly payment going forward.

    The Math Behind the Decision

    Let's look at the numbers. Suppose your current monthly Social Security benefit is $2,500. If you elect the lump sum, your payment will be based on your benefit from six months ago—roughly 4% lower, or about $2,350 per month. You would receive a lump sum ($2,350 x 6 = $14,100), but your ongoing monthly benefit would start at the lower amount. Dividing the lump sum ($14,100) by the monthly difference ($150) gives about 94 months, or almost eight years. In other words, it will take eight years of receiving the higher benefit to make up for not taking the lump sum.

    Reasons to Take the Lump Sum

    There are situations where the lump sum makes sense:

    1. Immediate Financial Need:

    If you have bills, a major expense, or want to fund something important like a vacation, accessing the lump sum offers flexibility.

    2. Health Concerns:

    If your health is poor, the lump sum may be preferable. Social Security benefits cease at death, except for a $255 survivor payment. Taking the lump sum ensures you receive more of your entitled benefits within your lifetime.

    Reasons to Decline the Lump Sum

    For many, passing on the lump sum will be the wiser move, if you're healthy and likely to live at least eight years, your higher monthly benefit will surpass the lump sum. Something else to consider is if you're the higher-earning spouse, your survivor's benefits will be based on your monthly payment. Opting for a lower benefit reduces what your spouse would receive after your passing.

    Future cost-of-living increases are based on your initial benefit. Starting at a lower monthly payment means smaller dollar increases over time. Historically, Cost of Living Adjustments (COLA) average 2.8% per year; these can add up and compound. You also need to remember that receiving a lump sum may increase your taxable income for that year, possibly pushing you into a higher bracket or increasing taxes on your Social Security benefits. Ultimately, the decision is highly personal. Assess your health, financial needs, family longevity, and whether your spouse would depend on your benefit. Crunching the numbers will clarify your breakeven point.

    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



    Subscribe to Retire With Ryan
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    12 mins
  • How To Manage The Impact From the IRAN War On Your Retirement Portfolio, #299

    How To Manage The Impact From the IRAN War On Your Retirement Portfolio, #299
    Mar 31 2026
    The Iran War, which began on February 28, 2026, is impacting global markets and I'm pretty sure it's having an effect on your portfolio too. Over the past month, the S&P 500 has dropped about 6%, largely due to surging oil prices. With crude oil climbing as high as $100 a barrel and lingering uncertainty around the conflict's resolution, volatility is weighing heavily on retirement investments. We'll explore the implications for investors, discuss historical parallels with previous market shocks, and offer practical tips to navigate the fallout—whether you're looking to rebalance, automate your contributions, or take advantage of tax-loss selling. Stay tuned as I break down actionable strategies to manage your portfolio through these turbulent times, and hear why it's important to avoid overreacting despite the dramatic headlines. You will want to hear this episode if you are interested in... [00:00] Impact of the Iran war on the global market [02:55] Market movements since the Iran war began [05:20] Strategies for dealing with portfolio volatility [06:29] Why buy into the market right now [07.39] Rebalance your portfolio to prepare for retirement [08:50] Continue to automate your investments [10:14] Evaluate your underperforming investments [11:12] How to create a tax loss that works for you Oil Prices and Stock Market Declines Since the war began, the S&P 500 index has fallen approximately 6%, a drop largely attributed to a sharp increase in crude oil prices. Oil prices spiked from $67.29 per barrel on the eve of the conflict to as high as $100, currently stabilizing around $90 at the time of recording. This represents a 33% climb post-conflict climb and as much as a 50% jump compared to prices in recent months. This sudden rise is far from the norm, and it's a clear demonstration of how tensions in resource-rich regions can send shockwaves throughout global markets. Higher oil prices raise production costs across industries, cut into profits, and reduce consumer spending power—all factors that undermine future earnings and push stock valuations lower. Volatility Is Nothing New While the current drop may feel alarming, it's important to remember that market declines happen regularly and often recover just as quickly. President Trump's tariff proposals from the last year, pushed the S&P 500 down 18% before tensions eased and the market rebounded to close the year up 18%. This historical context reassures investors that dramatic events can have both short-lived and long-term effects, but resilience and recovery are common themes in market history. Strategies for Navigating Volatility I recommend several strategies for managing portfolio volatility, starting with the importance of viewing downturns as buying opportunities—using cash to "buy the dip" can be rewarding when markets recover, especially in sectors hit hard by recent declines, including technology. It's also important to regularly rebalance your asset allocation to maintain your preferred stock-bond mix, which helps manage risk and ensures you're not overexposed or underinvested as markets shift. The value of automated investment contributions takes advantage of dollar-cost averaging, so don't halt contributions during downturns, stay consistent for long-term growth. Periodically reviewing and potentially trimming persistently underperforming investments and considering tax-loss harvesting in taxable accounts are also key tactics—this can improve portfolio efficiency, allow for strategic tax deductions, and keep your investment plan on track without straying afoul of wash-sale rules. Looking Forward and Recovery Potential Market volatility is inevitable, especially in uncertain times, but history and sound investing principles remind us to avoid knee-jerk reactions. Take advantage of the situation by rebalancing, automating investments, evaluating underperformers, and using tax-loss harvesting to ensure your portfolio remains resilient. Downturns often lay the groundwork for future gains, and patient, disciplined investing pays off over time. 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 Subscribe to Retire With Ryan
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    15 mins
  • Should You Add a Transfer on Death Beneficiary to Your Assets? #298

    Should You Add a Transfer on Death Beneficiary to Your Assets? #298
    Mar 24 2026

    On the show this week, I'm talking all about the topic of probate and how adding a Transfer on Death (TOD) or Payable on Death (POD) beneficiary designation to certain assets can help you avoid your estate being tied up in the probate process.

    You'll learn which types of accounts allow for TOD or POD beneficiaries, why these designations might be preferable to joint tenancy, and the pros and cons of setting them up. I break down step-ups in cost basis, the impact on estate taxes, and touch on differences across states—plus considerations to make sure your estate plan actually fits your wishes.

    You will want to hear this episode if you are interested in...

    • 00:00 Understanding Transfer on Death designations

    • 03:05 Joint tenants with rights of survivorship

    • 04:37 Pros and cons of TOD and POD accounts

    • 09:03 Challenges of TOD in estate planning

    • 11:24 Process for establishing TOD beneficiaries

    • 13:00 Does TOD avoid probate?

    What Is a Transfer On Death (TOD) Designation?

    A Transfer on Death designation allows you to name one or more beneficiaries who will automatically receive ownership of your accounts or property when you pass away. Unlike retirement accounts and life insurance policies—which typically require you to name beneficiaries—many investment and bank accounts, such as mutual funds, brokerage accounts, and money markets, do not automatically offer this option. That's where TOD comes into play, bridging a critical gap in your estate planning.

    Pros and Cons of Using TOD and POD Accounts

    One of the main benefits of a Transfer on Death (TOD) is that it allows designated beneficiaries to inherit assets quickly and directly, often by providing just a death certificate and minimal paperwork, which means they can avoid prolonged probate proceedings. This quick turnaround not only spares beneficiaries the stress and uncertainty of waiting for a court-supervised process but also helps them sidestep probate fees and other complications. Beneficiaries can benefit from a full step-up in cost basis on inherited assets, potentially reducing capital gains taxes if they sell soon after inheriting. For individuals who want to ensure their loved ones receive specific assets efficiently—and without granting them any access or control during their lifetime—a TOD can be an appealing tool.

    However, while TOD accounts streamline asset transfer, they can introduce challenges if not coordinated carefully with a broader estate plan. For example, if you wish to provide ongoing financial support rather than a lump sum, a TOD may not be suitable because the beneficiary immediately gains control of the assets. This could present issues for beneficiaries who are not financially responsible or who qualify for government aid. Additionally, TOD designations override instructions in a will, which means any inconsistencies in how beneficiaries are named or assets are divided, could cause confusion or disputes. TOD accounts are convenient, but they require thoughtful coordination with other estate planning elements to avoid unintended consequences.

    Does TOD Always Avoid Probate?

    While TOD almost always avoids the probate process for the specific asset, state laws can vary. Some less populous or smaller estates may not need to open probate regardless, but others require probate for everyone, as it's a revenue-generating process.

    TOD and POD beneficiary designations offer an easy, low-cost way to keep more of your assets in your family's control, minimize delays, and potentially avoid the hassle of probate. Thoughtful planning addresses not just asset transfer, but also your heirs' needs and the tax implications. As with any estate tool, consider your specific circumstances and consult with a professional before making changes.

    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



    Subscribe to Retire With Ryan
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    18 mins
  • Tax Extension Mistakes to Avoid This Filing Season, #297

    Tax Extension Mistakes to Avoid This Filing Season, #297
    Mar 17 2026
    In the last episode, I discussed seven mistakes to avoid when filing your 2025 taxes. So in this episode, I'm going to discuss the tax-filing mistakes people can make when filing an extension. Here are the four most common extension errors that could cost you money, including misconceptions about payment deadlines, underestimating taxes, and the importance of understanding state-specific extension rules. You will want to hear this episode if you are interested in... [00:00] Mistakes that people can make if they're filing an extension [01:41] Importance of filing for an extension by the tax deadline [02:35] Distinction between failure-to-file and failure-to-pay penalties [03:53] Suggestions for estimating: using last year's tax return, factoring in income changes, or major events [06:09] Importance of reviewing and complying with state-specific deadlines and requirements [08:21] Filing an extension buys time for accuracy but doesn't delay payment obligations Avoiding Common Tax Extension Mistakes Tax season is a stressful time for many, and for those with complex finances, business obligations, or unexpected circumstances, filing a tax extension may seem like a wise solution. These are the four biggest mistakes people make when filing a tax extension, along with my practical tips to avoid penalties and unnecessary stress. Notifying the IRS The first—and perhaps most critical—mistake is assuming that wanting more time is enough. Extensions aren't automatic; they require formally notifying the IRS by filing Form 4868 by the standard tax deadline, usually April 15th. Without this key step, the IRS will consider your return late, resulting in penalties. If nothing else, mark this on your tax checklist: file Form 4868 on time, every time. Extension to File Isn't Extension to Pay A widespread misconception is that an extension grants extra time to pay taxes due. Only your paperwork deadline shifts, your payment due date does not. Any unpaid federal taxes accrue interest from the original deadline, and failure-to-pay penalties start after April 15th. In fact, failing to file entirely triggers even steeper penalties. Estimate your tax liability and pay what you owe, even if you're still finalizing the details. Overestimating is safer, as any excess will be refunded after you fill it in. The Hidden Danger of Inaccurate Estimates Filing an extension isn't a hall pass to put off financial reckoning. You're still required to estimate how much you owe—a process that can trip up those who experienced income changes, investment gains, asset sales, or one-time distributions. The IRS expects most to pay either 90% of their current-year tax liability or 100% of last year's taxes (110% for high earners with AGI over $150,000) by the deadline to avoid penalties. Miss these benchmarks, and you could face interest or underpayment penalties—even if you settle up once you eventually file. Review your prior year's return and factor in any unusual income for the year. If in doubt, partner with a tax professional or use IRS Form 1040-ES for guidance. Don't Overlook State Tax Extension Rules One major mistake is forgetting—or not knowing—that state tax extension rules often differ from the IRS. Some states, like Connecticut, sync with federal extensions only if you owe nothing additional; if you do, you'll need to file a state-specific extension. New York requires its own extension form, and most states expect payment by their deadline, regardless of a federal extension. Double-check your state tax agency's website or contact a professional. Often, a separate state extension is mandatory, and missing this step can come with its own set of penalties. Plan for a Stress-Free Tax Extension Filing a tax extension can buy valuable time, but it's not a financial "pause" button. Always file Form 4868 (and any state-specific forms) on time. Pay the lesser of 90% of current-year or 100% (or 110% for high earners) of last year's tax by the April deadline, and study your state's requirements—federal rules don't always apply. Being proactive can save you hundreds (or thousands) in penalties and give you the space to file correctly and confidently later in the year. Resources Mentioned IRS Form 1040-ES IRS Form 4868 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 Subscribe to Retire With Ryan
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    10 mins
  • 7 Tax Mistakes to Avoid When Filing Your 2025 Taxes, Ep#296

    7 Tax Mistakes to Avoid When Filing Your 2025 Taxes, Ep#296
    Mar 10 2026

    Tax season is here, and if you're just now gathering your documents to file your return—or preparing them for your CPA—this is the time to slow down and make sure you're not making costly mistakes. In this episode, I walk through seven tax mistakes I frequently see both tax preparers and self-filers make when filing their returns. Some of these errors seem simple on the surface, but they can lead to penalties, missed deductions, delayed refunds, or paying more taxes than necessary. My goal in this episode is to help you avoid these pitfalls so you can file confidently and keep more of your money where it belongs.

    You will want to hear this episode if you are interested in…

    • [00:00] Why tax season mistakes are more common than you might think

    • [01:00] The costly consequences of filing after the tax deadline

    • [02:30] Why double-checking basic personal information matters more than you think

    • [03:30] The hidden risk of missing 1099 forms in the digital age

    • [04:15] How a rollover mistake can accidentally create taxable income

    • [05:00] The surprisingly common issue of unsigned tax returns

    • [05:30] Why simple math errors can lead to penalties or unexpected refunds

    • [06:30] When free tax preparation help may—or may not—be a good option

    The Most Common Tax Filing Errors

    Many tax mistakes don't happen because people are careless. They happen because people rush, assume something was already handled, or simply overlook a small detail that turns into a big issue later. One of the most common problems I see is filing past the tax deadline. Each year millions of taxpayers fail to file by the April deadline, which can trigger penalties and interest if taxes are owed. Even if you're due a refund, filing late can delay getting your money back.

    Another major issue is incomplete or incorrect information on the return. Something as simple as entering the wrong bank account for a direct deposit or forgetting to include a tax document can delay processing or create unnecessary headaches. And in today's digital world, many tax forms are delivered electronically, which means it's easier than ever to overlook a 1099 if you forget about an account.

    Missing Deductions and Overlooking Opportunities

    Beyond basic filing errors, many taxpayers lose money by missing deductions or not understanding new tax rules. Starting with the 2025 tax return, several changes introduced under the "One Big Beautiful Bill Act" create additional tax breaks. These include adjustments to the standard deduction, expanded deductions for certain taxpayers, and other potential opportunities many filers may not even realize exist.

    I also discuss why deciding between the standard deduction and itemizing can significantly affect how much tax you owe. In recent years, higher standard deductions meant fewer people itemized their taxes. But changes to the state and local tax deduction cap may reopen the door for some taxpayers to itemize again, especially homeowners with mortgages or individuals paying higher state and local taxes.

    Understanding what qualifies as an itemized deduction—from mortgage interest to medical expenses and charitable contributions—can make a meaningful difference in your tax outcome.

    Retirement Contributions and Quarterly Tax Pitfalls

    Two other mistakes I see regularly involve retirement and tax planning details that often get overlooked. Some taxpayers make IRA or Health Savings Account contributions but forget to report them properly on their return. That mistake can cause them to miss legitimate deductions that could reduce their taxable income.

    Another issue is failing to pay quarterly estimated taxes. This commonly affects self-employed individuals, business owners, and retirees who receive income without automatic tax withholding. Without proper withholding or estimated payments, taxpayers may face penalties—even if they eventually pay the full amount owed.

    The good news is that many tax mistakes can be corrected. If you discover an issue after filing, an amended return can often resolve the problem. But catching these issues before filing is always the best strategy.

    Resources Mentioned

    • Fidelity HSA

    • RetireWithRyan.com/podcast/296

    Connect With Ryan

    • Subscribe to the Retire With Ryan YouTube Channel

    • Download my entire book for FREE
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    23 mins