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_outlineIf you’ve spent any time on social media or read personal finance blogs, you’ve likely encountered a buzz around Roth IRAs and, specifically, Roth conversions. This week I’m discussing the details of Roth conversions, what they are, how they work, and why they’re crucial for those looking to optimize their retirement finances.
Roth IRAs hold a special appeal: the promise of tax-free income in retirement. And most people would agree that having tax free income in retirement is preferable over having taxable income. Yet, for many people, especially those in their 50s and older, most of their retirement savings sit in pre-tax accounts such as traditional IRAs or 401(k)s. Roth conversions offer a pathway for transforming those tax-deferred assets into tax-free retirement income.
This episode is packed with practical insights to help you make informed decisions about your financial future. Tune in to learn more and get ready to take your retirement planning to the next level!
You will want to hear this episode if you are interested in...
- [00:00] The appeal of tax-free income during retirement.
- [04:43] Key rules for Roth conversions.
- [08:53] Roth conversion strategies for wealth.
- [11:58] Roth IRA conversion strategy.
- [14:47] Roth conversion planning tips.
Breaking Down Roth IRA Conversions
A Roth IRA conversion involves moving funds from a pre-tax retirement account, like a traditional IRA or 401(k), into a Roth IRA. This process requires you to pay taxes now on the amount you convert, but it grants you future tax-free withdrawals. Anyone with pre-tax retirement funds can consider a conversion, but it’s important to understand the rules: Every time you do it, it starts a new five year holding period on the money. If you withdraw converted funds too soon, you might face taxes or penalties.
One clever strategy we’ll discuss is the Roth conversion ladder. By converting sums incrementally over several years, you gradually move money into the Roth IRA, allowing each batch to satisfy the five-year holding requirement. This helps maximize flexibility and minimize penalties if you need access in retirement.
Who Should Consider Roth Conversions?
So, who stands to gain the most from Roth conversions? Here are a few key candidates:
- Those anticipating higher future tax rates: If you’re in a low tax bracket now but expect to be in a higher one later, converting at today’s lower rates can save you significant money down the road.
- Anyone wishing to avoid required minimum distributions (RMDs): Roth IRAs aren’t subject to RMDs, making them valuable for those who want more control over retirement withdrawals.
- Individuals aiming to leave a tax-free inheritance: Paying conversion taxes now could shield heirs from larger tax bills, especially if they’ll be in a higher bracket.
- Retirees seeking flexibility: Having both taxable and tax-free buckets to draw from allows for smart tax-efficient withdrawals.
- Timing is also critical. Converting in years when your income dips, due to sabbaticals, career changes, or early retirement, can dramatically lower the tax impact of conversion.
How to Calculate If a Roth Conversion Makes Sense
It’s tempting to jump into conversions, but I advise running the numbers. Consider a hypothetical: If you convert $50,000 at a 12% federal and 5.5% state tax rate, you pay $12,055 in taxes upfront. If you left the funds in a traditional IRA and paid taxes on withdrawals in retirement at a similar rate, the outcome might be similar, but if future rates rise, the Roth wins out.
The more time your converted money has to grow, the greater the tax-free benefit. And if you can pay conversion taxes from outside the retirement account, your Roth can grow even more efficiently.
Steps to Execute a Roth IRA Conversion
Ready to act? Here’s an overview of the process:
- Open a Roth IRA at your provider.
- Transfer funds from your pre-tax account.
- Decide how much to convert and how you’ll pay the taxes (from conversion or other accounts).
- Complete the paperwork.
- Invest the funds, you want growth!
- Report conversions on your taxes, especially using IRS Form 8606.
Roth conversions are a powerful but nuanced strategy. If you’re nearing retirement, anticipate higher future tax rates, or want flexibility and legacy benefits, it may be time to explore this option. I’d advise you to consult a financial advisor familiar with your specific circumstances before you make any financial decisions, doing so ensures your Roth conversion fits seamlessly into your broader retirement plan, maximizing tax-free growth for years to come.
Resources Mentioned
- Retirement Readiness Review
- Subscribe to the Retire with Ryan YouTube Channel
- Download my entire book for FREE
- Charles Schwab
Connect With Morrissey Wealth Management
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