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Retirement Reality Check, with Michael Sheldon #256

Release Date: 06/03/2025

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...

Education Planning After the One Big Beautiful Bill Act: Key 529 Plan Changes, #270

Retire With Ryan

Paying for education is a major expense for many families, so I’m breaking down why 529 plans remain the preferred way to save for college, thanks to their tax advantages and flexible growth. I unpack updates, such as increased limits for K-12 tuition withdrawals, expanded uses for trade and vocational schools, and the new ability to roll funds into ABLE accounts for individuals with disabilities. Plus, learn about the new Trump accounts, the option to roll over leftover 529 funds into your child’s Roth IRA, and strategies to make the most of your education savings. Whether you’re...

Maximizing Spousal Social Security Benefits for Married Couples, #269

Retire With Ryan

For married couples planning their retirement, understanding spousal Social Security benefits can seem like a labyrinth. This week, I’m answering a listener's question about how spouses can maximize their Social Security benefits. Join me as I break down the key rules, eligibility requirements, and strategies that can help you and your spouse make the most of your benefits over your lifetimes. Whether you're nearing retirement or still a few years away, I can help you understand primary insurance amounts, full retirement age, and what happens if one spouse claims benefits early. If you...

Understanding HSA Changes for 2026, #268

Retire With Ryan

The power of Health Savings Accounts (HSAs) as a tool for both managing health expenses and building your retirement savings is often overlooked. On this episode, I’m sharing the basics of HSAs, highlighting their triple tax-free advantage, and explaining why they might be one of the best ways to maximize your retirement savings, even compared to more familiar accounts like IRAs and 401(k)s. I also unpack some important upcoming changes to HSAs thanks to the One Big Beautiful Bill Act, set to take effect in 2026. These changes expand HSA eligibility, especially for those on healthcare...

Surviving the ACA Subsidy Cliff, #267

Retire With Ryan

The future of Affordable Care Act (Obamacare) subsidies is a pressing issue for retirees and anyone shopping for health insurance on the ACA marketplace. With the generous subsidies brought by the American Rescue Plan Act set to expire at the end of 2025, I break down exactly how these subsidies work, what changes are coming in 2026, and what that means for your wallet. We’re talking eligibility thresholds, how income is calculated, why premiums might rise, and—most importantly—shares practical strategies for lowering your adjusted gross income to continue qualifying for subsidies...

Understanding the New Charitable Contribution Rules from the One Big Beautiful Bill Act, #266

Retire With Ryan

The One Big Beautiful Bill Act affects charitable contributions for retirees and individuals considering their tax strategies. I’m walking you through three major changes: the restoration of the charitable cash deduction for non-itemizers, new limitations on how much can be deducted for larger contributions, and a cap on itemized deductions for high earners. Whether you give to charity every year, are planning a large gift, or just want to maximize your tax benefits, I’m sharing practical tips about when and how to make your contributions in light of these updates. You will want to hear...

Should You Open a Trump Account for Your Child’s Future? #265

Retire With Ryan

The brand-new “Trump account” is a tax-deferred savings option for American children created by the One Big Beautiful Bill Act. I break down who’s eligible for up to $1,000 in free government contributions, how these accounts work, and how they stack up against other popular savings vehicles like 529 plans, IRAs, custodial accounts, and regular brokerage accounts. If you’re a parent or grandparent thinking about the best way to jumpstart your child’s financial future, you’ll want to tune in for my honest comparison of the Trump account's pros, cons, and quirks, plus tips on making...

How the One Big Beautiful Bill Act Impacts Retirees, #264

Retire With Ryan

The One Big Beautiful Bill Act, signed into law on July 4th, brings about several important tax changes. I’m discussing what these updates mean, especially for retirees, and sharing practical advice on how to take advantage of new deductions and avoid unexpected tax hits. From permanent adjustments to tax brackets and an increased standard deduction, to special benefits for those aged 65 and older, I cover everything you need to know to optimize your retirement strategy. Whether you're curious about Social Security taxation, itemized deductions in high-tax states, or planning smart...

Required Minimum Distributions Explained, #263

Retire With Ryan

This week on the show, we’re discussing the specifics of Required Minimum Distributions (RMDs) as we head into the second half of 2025. Whether you’re approaching your first year of RMDs or have been taking them for a while, I break down everything you need to know, from when you need to start taking distributions based on your birth year, to how RMDs are calculated, which accounts are affected, and the potential tax consequences for missing a withdrawal. I’m also sharing eight practical strategies you can use to lower your future RMDs, including asset diversification, Roth conversions,...

How the Big Beautiful Bill Impacts Solar & EV Tax Credits, #262

Retire With Ryan

With the recent passage of the Inflation Reduction Act, also known as the Big Beautiful Bill, significant changes are coming to both solar panel and electric vehicle tax credits. I break down what these changes mean, how they can affect your savings, and what steps you might want to take before these credits disappear. From figuring out if solar panels make sense for your home to understanding how electric vehicle credits work (and when they’re expiring), this episode is packed with actionable insights and tips, especially for those planning for retirement or looking to cut down on...

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.