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...
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7 Best Investment Options To Preserve Your Money in 2026, #288
Retire With Ryan
This episode is your introduction to the world of conservative investing, so it’s perfect for you if you’re looking to preserve your principal and grow your money at a steady pace. I’m walking you through seven standout investment choices for 2026, ranging from high-yield online money market accounts to short-term bond funds, CDs, and Treasury bonds. We’ll discuss how to shop around for the best rates, the importance of keeping up with inflation in retirement, and the benefits and limitations of each strategy. There’s something here for anyone who wants their money to work a little...
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4 Things All Successful Retirees Do, #287
Retire With Ryan
In this episode, I’m helping you kick off 2026 by reflecting on financial habits that pave the way for a successful retirement. As we set our goals for the year ahead, I share the four key traits I’ve observed in successful retirees, drawn from years of experience working with people from all walks of life. You’ll hear practical advice on how to work hard and invest consistently, the importance of living within your means, and ways to avoid common investment pitfalls that can derail your progress. Whether you’re just starting your retirement planning or fine-tuning your financial...
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6 Stock Market Predictions For 2026, #286
Retire With Ryan
As we turn the calendar to 2026, I reveal my forecasts for the stock market, interest rates, and top asset classes, and take a look back at how my 2025 predictions stacked up against reality. From the S&P 500’s rollercoaster performance to the ongoing rivalry between growth and value stocks, and even a showdown between bitcoin and gold, I break down what the numbers were, where I hit the mark, and where I missed. You’ll also hear my insights on international versus U.S. stocks, the outlook for small caps, and what the Federal Reserve might do with interest rates in the year ahead. Get...
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Most Asked Financial Questions of 2025, #285
Retire With Ryan
2025 has been a year of significant highs and lows, a bittersweet time marked by personal loss but also tremendous growth in our community of listeners and clients. As we wrap up the year, I wanted to take a moment to reflect and, more importantly, to give back by answering the most pressing questions on your minds. In this episode, I’m tackling the top 10 most asked financial questions I received in 2025 from both clients and listeners. From the future solvency of Social Security and the reality of rising inflation to the specifics of Bitcoin and long-term care, we are covering the topics...
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Top 5 Tax Benefits of 529 Plans, #284
Retire With Ryan
529 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...
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4 Ways To Receive A Tax Deduction For Charitable Contributions in 2025 and 2026, #283
Retire With Ryan
In the season of giving, we’re discussing making charitable contributions in 2025 and 2026. Americans are known for their generous donations to worthy causes, but understanding the best ways to give and maximize your tax benefits is key. This episode covers four effective strategies for making charitable contributions, from utilizing Qualified Charitable Distributions (QCDs) from your retirement accounts to cash donations, gifting highly appreciated stock or real estate, and using donor-advised funds. I also break down recent and upcoming tax law changes that impact your ability to itemize...
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
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