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6 Stock Market Predictions For 2026, #286

Release Date: 12/30/2025

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...

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...

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...

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...

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...

2026 Medicare Part B Premium Surprises, #282

Retire With Ryan

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...

7 Year End Tax Moves For Pre-Retirees in 2025, #281

Retire With Ryan

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...

Major Changes Coming To 401K, 403B, and 457 Retirement Plans in 2026, #280

Retire With Ryan

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...

Mapping Out A Plan For Roth Conversions, #279

Retire With Ryan

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...

Social Security 2026 Cost Of Living Update, #278

Retire With Ryan

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,...

More Episodes

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 ready for smart strategies, listener thank-yous, and a dose of investing reality as I help you set expectations (and goals) for the year to come!

You will want to hear this episode if you are interested in...

00:00 Happy New Year!
04:34 S&P 500 Trends and Predictions.
07:49 Market Trends & 2025 Predictions.
08:54 Bitcoin vs Gold & Stock Returns.
11:17 Importance of diversifying with international stocks.
14:20 Investment Predictions for 2026.
17:36 Stay invested to make the best financial gains.

How did my 2025 market predictions fare?

2025 turned out to be another rollercoaster, with both triumphs and challenges for investors. Beginning with an impressive performance, the S&P 500 flirted with a 20% annual return, after two previously remarkable years (+25% in 2023 and +23% in 2024). Volatility struck early in April due to concerns about tariffs and political tensions, leading the index to drop as much as 18% year-to-date before rebounding sharply.

The market often experiences significant intra-year declines, on average, 14-15% since the 1970s, so these swings are more common than many investors realize. Despite underestimating the final S&P 500 return in my 2025 prediction, it’s important to stick with your plan through turbulence.

Growth vs. Value

One of the perennial debates in investing is whether growth stocks (think Apple, Nvidia, and Microsoft) or value stocks (like JPMorgan, Walmart, and Berkshire Hathaway) will come out on top. While value historically outperformed over the long term, the last decade and a half has belonged to growth. I predicted value would outperform in 2025, but growth eked out the win yet again, maintaining its streak. The ETF comparison, Vanguard’s VONG for growth and VONV for value, shows just how close the race was, with both categories putting up strong numbers.

Large vs. Small Caps: The Size Dilemma

Size matters in investing, particularly when it comes to large-cap (S&P 500) versus small-cap (Russell 2000) stocks. I expected small caps to shine in 2025, but large caps led for the fifth consecutive year. The good news is that small caps narrowed the gap, hinting that a turnaround could be on the horizon as economic and regulatory shifts potentially favor these underdogs.

Bitcoin vs. Gold

For those seeking diversification, Bitcoin and gold are often top contenders. After years of jaw-dropping surges and gut-wrenching drops for Bitcoin, 2025 saw gold steal the spotlight with a phenomenal gain, its best showing since the 1970s, while Bitcoin stumbled. Still, I believe Bitcoin’s day in the sun isn’t over and predict it will bounce back in 2026.

U.S. vs. International

Global diversification hasn’t paid off for U.S. investors in recent years, as U.S. stocks consistently outpaced their international counterparts. In 2025, the tides turned and international stocks delivered their strongest performance in 15 years, besting the S&P 500’s return. It’s a timely reminder not to ignore the opportunities abroad, even if I feel U.S. equities still have the edge for 2026 due to ongoing innovation and growth potential.

Interest Rates and Federal Reserve

Few factors move markets like interest rate decisions. Predicting three cuts and a year-end rate of 3.5–3.75%, I called it accurately for 2025. Looking to 2026, I expect another two cuts, with possible changes in leadership at the Fed adding an extra dose of uncertainty.

Key Takeaways for 2026

So, what’s the game plan for the coming year? I predict a tempered 8.5% return for the S&P 500, a possible value and small-cap renaissance, Bitcoin’s comeback, U.S. stocks leading, and a cautious but optimistic approach to interest rates. But the most valuable advice is to stay invested. Market timing is notoriously difficult, and missing just a few of the market’s best days can devastate long-term returns. For those investing for a comfortable retirement, discipline and diversification remain your best allies.