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_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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