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Retire With Ryan

Retire With Ryan

著者： Ryan R Morrissey
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概要

 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 個人ファイナンス 経済学
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  • Tax Extension Mistakes to Avoid This Filing Season, #297

    Tax Extension Mistakes to Avoid This Filing Season, #297
    2026/03/17
    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 分
  • 7 Tax Mistakes to Avoid When Filing Your 2025 Taxes, Ep#296

    7 Tax Mistakes to Avoid When Filing Your 2025 Taxes, Ep#296
    2026/03/10

    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 分
  • What We Still Don't Know About Trump Accounts, Ep#295

    What We Still Don't Know About Trump Accounts, Ep#295
    2026/03/03
    If you watched President Trump's recent State of the Union address, you probably heard about the new Trump accounts, also known as 530A accounts. In this episode, I break down how these tax-advantaged investment accounts are designed to work, who qualifies, and—just as importantly, what we still don't know. There's been a lot of excitement, especially around the $1,000 seed money for eligible children. But before you rush to open one, there are several unanswered questions that deserve your attention. What Are Trump Accounts—and Who Qualifies? Trump accounts were introduced under the 2025 "Big Beautiful Bill Act" and are designed to help U.S. children build long-term wealth. Parents, grandparents, and others can contribute up to $5,000 per year per child until age 18. To jumpstart participation, children born between January 1, 2025, and December 31, 2028, are eligible for a $1,000 federal seed contribution. Unlike a Roth IRA, these accounts do not require earned income to contribute. That's a major difference. Most children can't fund retirement accounts because they don't have income. These accounts are meant to give them a head start from birth. To qualify, a child must be a U.S. citizen, have a valid Social Security number, and be under age 18. Parents can apply either by filing IRS Form 4547 with their 2025 tax return or by visiting trumpaccounts.gov. You'll Want to Hear This Episode If You're Interested In… [01:00] How the $5,000 annual contribution limit works [01:45] Why these accounts don't require earned income [02:35] How to open an account through your tax return or online [03:00] The upcoming authentication process in May 2026 [03:40] Whether you can invest in individual stocks like Nvidia or Tesla [04:30] Why Treasury guidance suggests broad index funds instead [05:10] Whether billions in seed money could move the stock market [06:00] Which financial institutions may (or may not) offer these accounts [07:45] Potential gift tax filing requirements for contributions [08:45] How withdrawals at age 18 might be taxed The Investment Confusion and Market Impact One of the biggest points of confusion right now is how the funds will actually be invested. The Trump accounts website shows mockups featuring individual stocks like Nvidia, Caterpillar, Home Depot, and Tesla. That certainly grabs attention. But Treasury guidance suggests investments may be limited to broad U.S. equity index funds or mutual funds, not individual stocks. If that holds true, I actually think that may benefit most investors. Broad-based index funds have historically outperformed many individual stock pickers over time. But it's important to understand what you're signing up for before you contribute. Another question I address is whether these accounts could meaningfully impact the stock market. With over 3 million sign-ups already, the initial $1,000 seed funding could total more than $3 billion. Add in private contributions and potential employer matches, and that number could grow to $7–8 billion invested when markets reopen after July 4. That sounds significant, but compared to total daily trading volume, it's less than 2%. It may provide a small positive impact, but it's unlikely to cause a dramatic market surge. Taxes, Custodians, and the Big Unknown at Age 18 There are still major tax questions. Because contributions are considered gifts and the child doesn't have immediate access to the funds, this could create gift tax reporting complications. Even if contributions fall under the $19,000 annual exclusion (for 2026), a gift tax return may still be required due to the lack of "present interest." Then there's the big question: how will withdrawals be taxed at age 18? There's no upfront deduction for contributions, which means this isn't structured like a traditional IRA. But it's also not clearly a Roth. My expectation is that only the gains will be taxed, but we don't yet know whether that will be ordinary income or capital gains. Until we get final guidance, I strongly believe record-keeping will be critical. Track contributions carefully. If custodians change or records are lost, your child could face unnecessary tax complications later. For now, here's what we do know: if your child, or a grandchild, niece, or nephew, qualifies for the $1,000 seed money, make sure the account gets opened. Even with unanswered questions, that initial funding is meaningful. Resources Mentioned TrumpAccounts.gov RetireWithRyan.com Retirement Readiness on Demand Discount Code: RETIRE99 Connect With Ryan Subscribe to the Retire With Ryan YouTube ChannelDownload my entire book for FREE
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    12 分
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