Retire With Ryan
There are important changes coming to 401 (k), 403 (b), and 457 retirement plans in 2026, so I’m focusing on how these updates may impact catch-up contributions for individuals over age 50. With the Secure Act 2.0 on the horizon, higher earners will soon have to make their catch-up contributions as Roth (post-tax) rather than pre-tax contributions, potentially affecting their take-home pay and tax strategies. Tune in as I walk you through what you need to know, how to prepare for these new rules, and actionable steps to make the most of your retirement savings. You will want to hear...
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If 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...
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Retirement planning is an ever-evolving process, and staying informed about changes to Social Security, Medicare, and tax limits is crucial to making the most of your golden years. On this episode of Retire with Ryan, I’m sharing important updates on the 2026 Social Security cost of living adjustment (COLA), projected changes to Medicare Part B premiums, and strategies for managing income in retirement. The newly announced cost-of-living adjustment (COLA) for 2026 will see benefit checks rise by 2.8%. I break down how the yearly adjustments are calculated, why they matter for seniors,...
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With the term “financial advisor” being used so broadly these days, it’s harder than ever for retirees and investors to make sense of who’s actually guaranteed to act in their best interest. So let’s talk about the key responsibilities of fiduciaries, explore the differences between fee-only advisors and those who earn commissions, and go through why full disclosure and ongoing advice matter so much in your financial planning relationship. I share practical tips on how to vet potential advisors, whether you’re unhappy with your current one or searching for the right fit for the...
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Every year, Medicare Open Enrollment presents an important opportunity for retirees and individuals enrolled in Medicare to review, update, and make changes to their health and prescription drug coverage. If you’re on Medicare or approaching retirement, understanding the enrollment period and your options is crucial to ensuring comprehensive and cost-effective health care. I’m sharing the seven essential things you need to know to make the most of this important window. Whether you’re already enrolled in Medicare or want to stay ahead of your retirement planning, I explain key dates,...
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This episode is essential listening for anyone who’s inherited an IRA, especially in light of the game-changing SECURE Act. If you’ve inherited a retirement account from a non-spouse since 2020, this episode is packed with details you need to know to avoid unexpected tax bills and penalties. I explain the new rules for inherited IRAs, explaining the requirements and options for non-designated, non-eligible, and eligible designated beneficiaries. Whether you’re figuring out minimum distributions or seeking smart tax-planning strategies, you’ll get clear guidance on how these updates...
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You might have seen those viral articles promising a mysterious multi-thousand-dollar Social Security “bonus,” but are they actually legit? On the show this week, I separate fact from fiction, debunking the myths and sharing seven actionable strategies to help you get the most out of your Social Security over your lifetime. Whether you’re curious about how working longer, delaying your benefits, checking your earnings record, or understanding tax implications can impact your retirement paycheck, this episode is packed with valuable tips to help you make sure you’re not leaving...
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The Social Security Fairness Act, which was signed into law at the start of 2025, has been in effect for about nine months since this game-changing legislation repealed both the Windfall Elimination Provision and the Government Pension Offset, restoring and increasing Social Security benefits for millions of retirees, especially teachers and public employees who worked in jobs exempt from Social Security. In this episode, I discuss exactly who qualifies for these newly restored benefits, explain how the Social Security Administration is handling the rollout, and give you a step-by-step guide...
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It’s one of the most frequently asked questions by my clients as they prepare for retirement. And while a million dollars may sound like a lot, the reality is a bit more complex. There are several key factors to consider when planning your retirement, including factoring in taxes, evaluating withdrawal strategies, and understanding the cost of living where you plan to retire. Let’s break down how you can determine whether your nest egg will support your ideal retirement. You will want to hear this episode if you are interested in... [01:57] Evaluating if a million dollars is enough to...
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Are you turning 65 soon or starting to think seriously about healthcare in retirement? This week, I discuss the complicated world of Medicare—with a focus on the seven most costly mistakes people make when enrolling. From missing crucial deadlines and underestimating penalties, to overlooking the true costs Medicare doesn’t cover and getting tripped up by income-related surcharges, I give practical advice to help you avoid expensive pitfalls and make confident choices for your health and your wallet. Whether you’re working past 65, exploring Medicare Advantage and Medigap, or just...
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
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