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_outline529 college savings plans are a favorite tool for families looking to fund education, but recent updates have made them even more compelling. With the passing of the One Big Beautiful Tax Act in 2025, there have been some exciting changes to what you can use 529 funds for, including expanded coverage for K-12 tuition, test fees, vocational programs, and support for learning differences.
I also discuss the various tax advantages of contributing to a 529 plan, like state tax deductions, tax-deferred growth, and even the ability to roll leftover funds into a Roth IRA for your child. He offers real-life examples, highlights differences across state plans, and gives practical tips on maximizing your savings and tax benefits as the year wraps up.
If you’re looking to make the most out of your child or grandchild’s future education while being smart about your finances, this episode is packed with must-know information.
You will want to hear this episode if you are interested in...
- [00:00] 529 Plan updates and expansions.
- [06:48] 529 Plans: taxes and benefits.
- [08:02] 529 Plan tax-free growth.
- [09:55] Investment considerations for 529 plans.
- [13:49] New rules on 529-to-Roth IRA rollovers.
The Expanded 529 Universe
Most people know 529 plans are great for covering college tuition, room and board, and required fees. The One Big Beautiful Tax Act of 2025 has expanded what 529 distributions can cover, opening up a wider range of education-related expenses, including much earlier in a student’s academic journey.
Newly Eligible Expenses:
- K-12 Tuition: The annual limit for K-12 tuition expenses jumps from $10,000 to $20,000 in 2026.
- Test Fees and Credentialing: You can now use 529 funds to pay for standardized testing, college entry exams, and vocational credentialing programs.
- Homeschool & Specialized Support: Structured homeschool curricula, academic tutoring, therapies, and materials for diagnosed learning differences (including ADHD) are now eligible.
- Apprenticeships & Educational Equipment: Costs for apprenticeship programs and special technology or learning tools can now be covered.
However, there are still some limitations: transportation, school-purchased health insurance, and extracurricular activity fees remain ineligible.
State Tax Deductions
The state tax deduction is a unique benefit offered by many states for 529 contributions, but often families overlook this: over 30 states offer a tax break, but the rules vary. In Connecticut, for example, you can deduct up to $5,000 per person or $10,000 per couple from your state taxable income. You must usually contribute to your own state’s plan (though states like Arizona, Kansas, and Pennsylvania allow deductions for out-of-state plans). Be mindful of year-end deadlines, contributions must be made by December 31st to claim the deduction for that year. Even if your state benefit is modest, it’s essentially “free money” for doing something you’re likely planning anyway.
Student Loan Repayment and Rollovers to Roth IRAs
529 plans now offer more flexibility, even if the intended student doesn’t use all the funds for education.
- Student Loan Repayments: Up to $10,000 (lifetime) per beneficiary can be used to pay down qualified student loans, helping recent grads reduce their debt burden.
- Roth IRA Rollovers: As of recent law, up to $35,000 can be rolled from a 529 plan to a Roth IRA for the beneficiary, provided the 529 is at least 15 years old, the money isn’t a recent contribution, and the beneficiary has earned income. This can be an incredible jumpstart for retirement savings if college funds aren’t fully used.
All 529 plans are not created equal. Look for low-cost, direct-sold plans rather than advisor-sold plans that carry extra commissions. Every dollar saved on fees is another dollar that can grow tax-free in your account.
Resources Mentioned
- Retirement Readiness Review
- Subscribe to the Retire with Ryan YouTube Channel
- Download my entire book for FREE
- Fidelity Investments
Connect With Morrissey Wealth Management
www.MorrisseyWealthManagement.com/contact