What Order Should I Start Withdrawing From My Investment Accounts In Retirement, #318
Retire With Ryan
When you’re moving into retirement, you’re most likely to be starting to ask yourself which investment accounts you should start drawing from first. There’s really no universal answer—retirement withdrawal strategies are deeply personal and situation-dependent. But understanding the implications of each account type and the factors that influence withdrawal order can have a massive impact on your tax burden and the longevity of your assets. You will want to hear this episode if you are interested in... [00:00] Retirement withdrawal strategy options [06:37] Roth IRA and...
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3 Ways To Make The Most of Your Restricted Stock Units, #317
Retire With Ryan
On the show this week, I answer a listener question about restricted stock units, or RSUs—what they are, how they're taxed, and the best strategies for managing them as they vest. I'll take an in-depth look at different types of vesting schedules, tax implications, and the practical choices you have when your RSUs become available. This episode is all about giving you clear guidance to help you make informed decisions about RSUs and making sure your retirement strategy is on the right financial track. You will want to hear this episode if you are interested in... 00:00 Explanation of...
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Accessing Your 401k Early With The Rule of 55, #316
Retire With Ryan
For many Americans, the idea of retiring before age 59 and a half often seems out of reach, particularly when the bulk of their savings sits in an employer-sponsored 401(k) or 403(b) plan. Traditionally, the tax code penalizes early withdrawals from these accounts. However, the Rule of 55 could open the door to a more flexible, penalty-free early retirement. On this episode, I’ll share more about this IRS provision, who qualifies, how to use it wisely, and potential hazards to avoid. You will want to hear this episode if you are interested in... [00:00] Overview of the Rule of 55 and...
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How To Avoid Taxes On The Sale Of Your Primary Residence, #315
Retire With Ryan
For many retirees, their home isn't just a place of comfort, it’s one of the largest assets on their balance sheet. However, beyond the emotional value and the years of accumulated equity, there's an often-overlooked reality: selling your primary residence can bring an unexpected tax bill. If you’re contemplating a sale or want to ensure you’re planning wisely, understanding the IRS’s primary residence capital gains exclusion is essential. On the show this week, I break down what this exclusion means, who qualifies, how to maximize its benefits, and the critical planning steps to avoid...
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Give Your Child or Grandchild A Head Start On Retirement With a Trump Account, #314
Retire With Ryan
On July 4, 2026, a groundbreaking opportunity opened for parents and guardians aiming to give their children a head start on their financial journey: Trump Accounts. Created as part of the OBBA Tax Act (“One Big Beautiful Bill” Tax Act) of 2025, these tax-advantaged investment vehicles provide a unique way to grow wealth for minors. In this episode, I break down what Trump Accounts are, who’s eligible for generous bonuses, how to get started, and how they compare to other common savings options like 529 plans. You will want to hear this episode if you are interested in... [00:00]...
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Avoid These 7 Scenarios to Keep Your Medicare Premiums Lower In Retirement, #313
Retire With Ryan
Medicare brings peace of mind to millions of retirees, but for those with higher incomes, there’s an added layer of complexity called IRMAA—the Income Related Monthly Adjustment Amount. If your modified adjusted gross income (MAGI) crosses certain thresholds, you may end up paying substantially more for your Medicare Part B and Part D coverage. In this article, we break down how IRMAA works, outline common scenarios that may unexpectedly raise your premiums, and offer actionable strategies to help you avoid unnecessary costs during your retirement years. You will want to hear this...
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Do Actively Managed Funds Perform Better Than Index Funds In Volatile Markets? #312
Retire With Ryan
When it comes to planning for retirement, one of the most commonly faced decisions is how to invest for long-term growth and stability. In turbulent times, market volatility often generates renewed debate on whether index funds, or their actively managed counterparts, offer the better path for accumulating wealth. On this episode of the show, I’m unpacking what index funds are, how they stack up against actively managed funds, and what the latest data reveals about performance during both quiet and volatile markets. You will want to hear this episode if you are interested in... ...
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Is Your Money Safe With Schwab or Fidelity? #311
Retire With Ryan
This week, I’m tackling a question that’s on the minds of many investors: How safe is your money with major brokerage firms like Fidelity and Charles Schwab? In light of recent high-profile bank collapses and widespread concerns about financial security, I discuss how banks and brokerage firms operate differently, what protections exist for your investments, and what would happen if a major brokerage firm were to collapse. Whether you’re considering how best to safeguard your assets or wondering about the real risks of brokerage failures, this episode will provide the clarity and peace...
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How To Make Your Brokerage Account Work Like A Roth IRA, #310
Retire With Ryan
When it comes to planning for retirement, Roth IRAs have gained widespread attention for their tax-advantaged status and the promise of tax-free withdrawals in retirement. Financial experts, YouTubers, and podcasters have been touting the benefits of contributing to or converting assets into Roth accounts for years. But an often-overlooked vehicle could empower you to manage your investments just as efficiently: the humble taxable brokerage account. Surprisingly, with the right strategy, you can even pay 0% capital gains tax, mirroring one of the biggest appeals of a Roth. You...
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5 Reasons To Not Invest Your Retirement Savings In Variable Annuities, #309
Retire With Ryan
Variable annuities are often promoted as a secure way to generate guaranteed income during retirement, drawing the attention of retirees seeking stability for their nest eggs. But beneath the surface, these products frequently come with complications and costs that can erode your savings and limit your financial flexibility. In this episode, I share the details of the often-overlooked downsides of variable annuities and give you some important insights every investor should consider. You will want to hear this episode if you are interested in... [03:14] What is a Variable Annuity?...
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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