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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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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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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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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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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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...
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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