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_outlineAs 2025 comes to a close, we’re here to help you make the most of year-end tax planning. I’m explaining seven actionable strategies to help you minimize your tax liability and optimize your retirement savings before the New Year.
From maximizing retirement plan contributions and exploring Roth conversion opportunities to using donor-advised funds for charitable giving and getting the most from your health savings accounts, this episode is packed with practical advice. The insights I’m sharing in this episode will guide you through the essential moves you need to consider before December 31st.
You will want to hear this episode if you are interested in...
- [00:00] Year-end retirement contribution tips.
- [04:07] Mega Backdoor Roth IRA strategy.
- [08:51] Maximizing charitable tax benefits.
- [12:19] Year-end tax savings key insights.
- [16:24] Maximize HSA contributions strategically.
7 Essential Year-End Tax Planning Strategies for 2025
When the end of the year approaches, savvy savers and future retirees know it’s prime time to make smart financial moves. Here are my top seven actionable steps you can take before December 31st, and even a few after, to set yourself up for retirement success and optimize your tax situation.
1. Max Out Your Retirement Contributions
For 2025, the maximum contribution is $23,500 if you’re under 50 and $31,000 if you’re over 50 (including a $7,500 catch-up). Contributing up to these limits reduces your taxable income for the year and boosts your nest egg for retirement, especially important if you’re at your career’s earnings peak.
But don’t wait! Corporate payroll deadlines mean these contributions typically need to be made by year’s end. Self-employed individuals might have a little longer, but now is the best time to act. Setting yourself up for the new, higher 2026 limits can also help you keep your savings momentum going.
2. Utilize the Mega Backdoor Roth IRA
High earners who make too much for direct Roth IRA contributions aren’t out of options. The “Mega Backdoor Roth” strategy lets you contribute after-tax dollars beyond the standard 401(k) limits, then convert those funds into a Roth IRA or a Roth 401(k). For 2025, total contribution limits (including after-tax) can be as high as $77,500 if you’re over 50.
This powerful move can supercharge your retirement savings with the potential for decades of tax-free growth. However, not all employer plans allow in-plan conversions, so check with your HR department to explore your options.
3. Consider Roth Conversions
A Roth conversion involves moving pre-tax money from a traditional IRA or 401(k) into a Roth account. You’ll owe taxes on the conversion, but if you’re in a low tax bracket this year, or expect to be in a higher one later, converting now could pay off substantially in future tax savings. Even small conversions ($10,000 - $20,000) can be beneficial if kept in lower tax brackets.
4. Maximize Charitable Contributions Using Donor-Advised Funds
Charitable giving is generous, but it’s also an opportunity to optimize taxes. Since the standard deduction now exceeds what many typically give, “bunching” several years’ worth of donations into a single year using a donor-advised fund can allow you to itemize and increase your deduction. For example, funding three years of donations at once could push your deductions over the standard threshold, providing a greater tax benefit.
5. Review Stock Options for Tax Efficiency
If you have stock options, especially non-qualified stock options or incentive stock options (ISOs), year-end is an ideal time to review their tax impact. Exercising during a low-income year can mean paying less tax on gains. ISOs, when held beyond the required periods, can qualify for long-term capital gains tax rates. Each type of stock option has distinct rules and opportunities for savings, so analyze your position before acting.
6. Use Flexible Spending Accounts (FSAs) Before They Expire
FSAs allow you to pay for medical expenses with pre-tax dollars, saving you the equivalent of your combined federal and state tax rates (often ~30%). For 2025, you can contribute up to $3,300. Remember: FSAs are “use it or lose it,” so spend down your balance, or you risk forfeiting unspent dollars, with only a limited carryover allowed. Also consider dependent care FSAs if you have eligible expenses.
7. Maximize Your Health Savings Account (HSA)
HSAs are financial powerhouses, offering triple tax benefits: contributions are deductible, growth is tax-free, and withdrawals for qualified medical expenses are untaxed. The 2025 limits are $4,300 for singles and $8,550 for families, plus an extra $1,000 catch-up if you’re over 55. Make sure employer contributions are factored into your personal limit, and if both spouses are eligible, consider separate accounts for maximum catch-up savings.
Year-end tax planning is your chance to make meaningful progress toward retirement readiness and tax efficiency. Whether you’re maximizing workplace plans, exploring Roth opportunities, leveraging charitable strategies, or optimizing account contributions, each move can compound into significant long-term benefits.
Resources Mentioned
- Retirement Readiness Review
- Subscribe to the Retire with Ryan YouTube Channel
- Download my entire book for FREE
- Charles Schwab
- Fidelity
- Vanguard
Connect With Morrissey Wealth Management
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