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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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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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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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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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...
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Healthcare planning is a huge part of getting ready for your retirement. In this episode, I tackle one of the most pressing updates for retirees: the latest changes to Medicare premiums for 2026, including important surcharges, deductibles, and strategies to help you manage your healthcare expenses. I’m helping you understand the significant increases in Medicare Part B premiums and deductibles, the impact these changes will have on your Social Security benefits, and why waiting to claim Social Security might pay off. Listen in to get helpful strategies for appealing IRMAA surcharges...
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As 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...
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There are important changes coming to 401 (k), 403 (b), and 457 retirement plans in 2026, so I’m focusing on how these updates may impact catch-up contributions for individuals over age 50. With the Secure Act 2.0 on the horizon, higher earners will soon have to make their catch-up contributions as Roth (post-tax) rather than pre-tax contributions, potentially affecting their take-home pay and tax strategies. Tune in as I walk you through what you need to know, how to prepare for these new rules, and actionable steps to make the most of your retirement savings. You will want to hear...
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If 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...
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Retirement planning is an ever-evolving process, and staying informed about changes to Social Security, Medicare, and tax limits is crucial to making the most of your golden years. On this episode of Retire with Ryan, I’m sharing important updates on the 2026 Social Security cost of living adjustment (COLA), projected changes to Medicare Part B premiums, and strategies for managing income in retirement. The newly announced cost-of-living adjustment (COLA) for 2026 will see benefit checks rise by 2.8%. I break down how the yearly adjustments are calculated, why they matter for seniors,...
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
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