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_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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