Libsyn Directory

Retirement Reality Check, with Michael Sheldon #256

Release Date: 06/03/2025

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,...

What is a Fiduciary Advisor and Why It Matters, #277

Retire With Ryan

With the term “financial advisor” being used so broadly these days, it’s harder than ever for retirees and investors to make sense of who’s actually guaranteed to act in their best interest. So let’s talk about the key responsibilities of fiduciaries, explore the differences between fee-only advisors and those who earn commissions, and go through why full disclosure and ongoing advice matter so much in your financial planning relationship. I share practical tips on how to vet potential advisors, whether you’re unhappy with your current one or searching for the right fit for the...

Switching Plans and Saving Money During Medicare’s Annual Open Enrollment, #276

Retire With Ryan

Every year, Medicare Open Enrollment presents an important opportunity for retirees and individuals enrolled in Medicare to review, update, and make changes to their health and prescription drug coverage. If you’re on Medicare or approaching retirement, understanding the enrollment period and your options is crucial to ensuring comprehensive and cost-effective health care. I’m sharing the seven essential things you need to know to make the most of this important window. Whether you’re already enrolled in Medicare or want to stay ahead of your retirement planning, I explain key dates,...

Key SECURE Act Insights on Avoiding 25 Percent Penalties on Inherited IRAs, #275

Retire With Ryan

This episode is essential listening for anyone who’s inherited an IRA, especially in light of the game-changing SECURE Act. If you’ve inherited a retirement account from a non-spouse since 2020, this episode is packed with details you need to know to avoid unexpected tax bills and penalties. I explain the new rules for inherited IRAs, explaining the requirements and options for non-designated, non-eligible, and eligible designated beneficiaries. Whether you’re figuring out minimum distributions or seeking smart tax-planning strategies, you’ll get clear guidance on how these updates...

Seven Essential Tips to Maximize Your Lifetime Social Security Benefits, #274

Retire With Ryan

You might have seen those viral articles promising a mysterious multi-thousand-dollar Social Security “bonus,” but are they actually legit? On the show this week, I separate fact from fiction, debunking the myths and sharing seven actionable strategies to help you get the most out of your Social Security over your lifetime. Whether you’re curious about how working longer, delaying your benefits, checking your earnings record, or understanding tax implications can impact your retirement paycheck, this episode is packed with valuable tips to help you make sure you’re not leaving...

What Retirees Need to Know About The Social Security Fairness Act, #273

Retire With Ryan

The Social Security Fairness Act, which was signed into law at the start of 2025, has been in effect for about nine months since this game-changing legislation repealed both the Windfall Elimination Provision and the Government Pension Offset, restoring and increasing Social Security benefits for millions of retirees, especially teachers and public employees who worked in jobs exempt from Social Security. In this episode, I discuss exactly who qualifies for these newly restored benefits, explain how the Social Security Administration is handling the rollout, and give you a step-by-step guide...

Is a Million Dollars Enough to Retire? #272

Retire With Ryan

It’s one of the most frequently asked questions by my clients as they prepare for retirement. And while a million dollars may sound like a lot, the reality is a bit more complex. There are several key factors to consider when planning your retirement, including factoring in taxes, evaluating withdrawal strategies, and understanding the cost of living where you plan to retire. Let’s break down how you can determine whether your nest egg will support your ideal retirement. You will want to hear this episode if you are interested in... [01:57] Evaluating if a million dollars is enough to...

Avoid These Seven Medicare Enrollment Mistakes and Protect Your Finances, #271

Retire With Ryan

Are you turning 65 soon or starting to think seriously about healthcare in retirement? This week, I discuss the complicated world of Medicare—with a focus on the seven most costly mistakes people make when enrolling. From missing crucial deadlines and underestimating penalties, to overlooking the true costs Medicare doesn’t cover and getting tripped up by income-related surcharges, I give practical advice to help you avoid expensive pitfalls and make confident choices for your health and your wallet. Whether you’re working past 65, exploring Medicare Advantage and Medigap, or just...

More Episodes

This week on the show, I’m joined in person by investment veteran Michael Sheldon, who brings over 26 years of experience in the financial services industry. We dig into essential strategies for investing as you approach and enter retirement, covering asset allocation, diversification, income planning, and how to handle inevitable market volatility.

Whether you’re a pre-retiree, a recent retiree, or just looking to strengthen your investment approach, Michael offers some great actionable insights designed to help you build a resilient portfolio and stay on track toward your long-term financial goals.

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

[04:52] Portfolio risk should change as you age, becoming more conservative in retirement.
[09:34] Why US large-cap stocks have outperformed recently.
[14:13] Pros and cons of target date funds, including fees, asset allocation, and international exposure.
[16:07] Michael warns against chasing high-yield dividend stocks.
[18:51] Private equity/real estate and understanding the liquidity and risks.
[31:15] Building income streams, reducing volatility, and portfolio standard deviation as you near retirement.
[43:18] Why maintaining discipline through corrections is key to investment success.

Strategies to Weather Market Ups and Downs

Any successful investment journey begins with a clear financial plan. Michael emphasizes the importance of understanding your spending needs in retirement. This process often starts with creating a detailed budget. A thorough assessment of current and expected future expenses helps determine the appropriate rate of return necessary to achieve your retirement goals.

Once you have a handle on your budget, you can set a target allocation that aligns your risk tolerance with your required investment returns. Your personal plan should factor in not only your goals and time horizon, but also your comfort level with market volatility.

Balancing Risk and Opportunity

As you move closer to retirement, adjusting your asset allocation becomes increasingly important. Younger investors can often afford to be more aggressive, allocating a larger portion (often 70% - 100%) to equities, since they have time to recover from market downturns. However, those approaching or in retirement generally benefit from more conservative portfolios, emphasizing capital preservation.

A common rule of thumb discussed was to maintain 3 - 5 years of living expenses in cash or short-term bonds. This buffer allows retirees to weather market downturns without selling equities at a loss. Still, every investor is different. Some retirees, especially those with higher risk tolerance or substantial resources, may maintain large allocations to equities. The key is to structure your portfolio to ensure you can meet your expenses even during extended market declines.

Don’t Chase Home Runs

The conversation stressed the dangers of seeking the next “big winner” stock. Instead, the focus should be on diversification, owning a broad mix of asset classes and geographies. While the past decade has seen U.S. large-cap growth stocks outperform other areas, this may not always be the case. International markets, small-cap stocks, and value stocks each tend to outperform at different points in the economic cycle.

Proper diversification can help reduce risk and smooth out returns, preventing the common mistake of buying high and selling low. It’s wise to avoid concentrating your portfolio too heavily in a single sector, country, or investment style.

Beyond Chasing High Dividends

One of the big myths in retirement investing is the need to load up on high-dividend-paying stocks for income. Michael cautioned against focusing solely on high yields, as these companies might carry more risk or have unsustainable business models. Instead, look for companies with a solid history of gradually increasing their dividends, which indicates healthy cash flows and business stability.

Active vs. Passive Management and Cost Considerations

The debate between active and passive management continues. For broad U.S. markets, low-cost index funds and ETFs have outperformed most active managers over time, thanks to lower costs and automatic portfolio updates.

Increasingly, investors are turning to ETFs for their tax efficiency, tradability, and lower fees compared to traditional mutual funds. As with any investment, understanding fees and their impact on long-term returns is vital.

The Power of Discipline

Finally, Michael shares a valuable perspective on market volatility. Historically, the S&P 500 has experienced average intra-year declines of over 14%, yet finished positive in 76% of years since 1980. Volatility is normal, and patient investors are rewarded for staying invested.