Should You Add a Transfer on Death Beneficiary to Your Assets? #298
Retire With Ryan
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...
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Tax Extension Mistakes to Avoid This Filing Season, #297
Retire With Ryan
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...
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7 Tax Mistakes to Avoid When Filing Your 2025 Taxes, Ep#296
Retire With Ryan
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...
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What We Still Don’t Know About Trump Accounts, Ep#295
Retire With Ryan
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...
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Is It Wise to Gift My Children Money While I’m Alive? Ep#294
Retire With Ryan
If you have children and you’ve been thinking, “Why wait until I’m gone to help them financially?”—this episode is for you. In Episode 294, I walk through the biggest things to consider before making gifts to your kids while you’re still alive, and I break down some of the smartest ways to do it without triggering unnecessary taxes. I’m seeing this trend more and more with my clients, and it makes sense. Financial markets have performed well, real estate has surged, and many retirees are in a stronger position than generations before them. But just because you can gift money...
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Learn the ABCs of Medicare, Ep293
Retire With Ryan
If you’re approaching age 65, Medicare can feel overwhelming fast. Between Parts A, B, C, and D and the timing rules tied to each—it’s easy to make a costly mistake if you don’t understand how the pieces fit together. In this episode, I walk through the Medicare “alphabet,” explaining what each part does, when enrollment matters most, and how your decisions interact with the rest of your retirement plan. We also cover common questions that come up when clients transition from employer-sponsored coverage to Medicare for the first time. Whether retirement is right around the corner...
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6 Changes To Social Security Happening in 2026, #292
Retire With Ryan
The landscape of Social Security is changing yet again. As we enter 2026, six big changes will impact both current and future retirees. I break down everything from the new cost of living adjustment (COLA), increases in the earnings test limit, and updated eligibility requirements, all the way to shifts in the full retirement age and the solvency projections for the Social Security Trust Fund. You’ll also hear practical tips on maximizing your Social Security benefits, how to prepare for what’s ahead, and why it’s more important than ever to have a solid retirement plan in place. ...
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Protecting Your Schwab Accounts From A RAT Attack, #291
Retire With Ryan
Have you ever fallen victim to a RAT attack? No, not the furry kind, a Remote Access Trojan attack. I’m discussing how cybercriminals use social engineering to target victims, and the real-world impact these threats can have on your investment accounts and personal information. I reveal the latest tactics scammers use, and, most importantly, offer practical tips to help you recognize warning signs, safeguard your accounts, and minimize your risk, whether you’re an individual managing your retirement nest egg or a business owner overseeing company assets. You will want to hear...
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Can I Contribute to My 401(k) and a Traditional IRA in the Same Tax Year?, #290
Retire With Ryan
A listener recently wrote in with a common and important retirement planning question: If I’m already maxing out my 401(k), can I also contribute to a traditional IRA in the same year? The short answer is yes—but whether it makes sense, and how much benefit you receive, depends on your income, tax situation, and long-term goals. In this episode, I break down how traditional IRA contributions work alongside employer-sponsored retirement plans, when those contributions are deductible, and what options are available if your income is too high for a deduction. We also explore alternative...
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Top 5 Growth ETFs to Own For 2026 and Beyond, #289
Retire With Ryan
Last week, we covered the best investments to preserve your money, but this week we are shifting gears to focus on growth. For retirees, the goal is to have an income that outpaces inflation, and historically, the best way to achieve that is by having 50% to 70% of your portfolio invested in stock funds. In this episode, I break down five specific Exchange Traded Funds (ETFs) that can help you grow your wealth in 2026. I discuss why I prefer ETFs over mutual funds, specifically focusing on cost, transparency, and liquidity, and provide the exact ticker symbols and expense ratios for the funds...
info_outline529 college savings plans are a favorite tool for families looking to fund education, but recent updates have made them even more compelling. With the passing of the One Big Beautiful Tax Act in 2025, there have been some exciting changes to what you can use 529 funds for, including expanded coverage for K-12 tuition, test fees, vocational programs, and support for learning differences.
I also discuss the various tax advantages of contributing to a 529 plan, like state tax deductions, tax-deferred growth, and even the ability to roll leftover funds into a Roth IRA for your child. He offers real-life examples, highlights differences across state plans, and gives practical tips on maximizing your savings and tax benefits as the year wraps up.
If you’re looking to make the most out of your child or grandchild’s future education while being smart about your finances, this episode is packed with must-know information.
You will want to hear this episode if you are interested in...
- [00:00] 529 Plan updates and expansions.
- [06:48] 529 Plans: taxes and benefits.
- [08:02] 529 Plan tax-free growth.
- [09:55] Investment considerations for 529 plans.
- [13:49] New rules on 529-to-Roth IRA rollovers.
The Expanded 529 Universe
Most people know 529 plans are great for covering college tuition, room and board, and required fees. The One Big Beautiful Tax Act of 2025 has expanded what 529 distributions can cover, opening up a wider range of education-related expenses, including much earlier in a student’s academic journey.
Newly Eligible Expenses:
- K-12 Tuition: The annual limit for K-12 tuition expenses jumps from $10,000 to $20,000 in 2026.
- Test Fees and Credentialing: You can now use 529 funds to pay for standardized testing, college entry exams, and vocational credentialing programs.
- Homeschool & Specialized Support: Structured homeschool curricula, academic tutoring, therapies, and materials for diagnosed learning differences (including ADHD) are now eligible.
- Apprenticeships & Educational Equipment: Costs for apprenticeship programs and special technology or learning tools can now be covered.
However, there are still some limitations: transportation, school-purchased health insurance, and extracurricular activity fees remain ineligible.
State Tax Deductions
The state tax deduction is a unique benefit offered by many states for 529 contributions, but often families overlook this: over 30 states offer a tax break, but the rules vary. In Connecticut, for example, you can deduct up to $5,000 per person or $10,000 per couple from your state taxable income. You must usually contribute to your own state’s plan (though states like Arizona, Kansas, and Pennsylvania allow deductions for out-of-state plans). Be mindful of year-end deadlines, contributions must be made by December 31st to claim the deduction for that year. Even if your state benefit is modest, it’s essentially “free money” for doing something you’re likely planning anyway.
Student Loan Repayment and Rollovers to Roth IRAs
529 plans now offer more flexibility, even if the intended student doesn’t use all the funds for education.
- Student Loan Repayments: Up to $10,000 (lifetime) per beneficiary can be used to pay down qualified student loans, helping recent grads reduce their debt burden.
- Roth IRA Rollovers: As of recent law, up to $35,000 can be rolled from a 529 plan to a Roth IRA for the beneficiary, provided the 529 is at least 15 years old, the money isn’t a recent contribution, and the beneficiary has earned income. This can be an incredible jumpstart for retirement savings if college funds aren’t fully used.
All 529 plans are not created equal. Look for low-cost, direct-sold plans rather than advisor-sold plans that carry extra commissions. Every dollar saved on fees is another dollar that can grow tax-free in your account.
Resources Mentioned
- Retirement Readiness Review
- Subscribe to the Retire with Ryan YouTube Channel
- Download my entire book for FREE
- Fidelity Investments
Connect With Morrissey Wealth Management
www.MorrisseyWealthManagement.com/contact