Libsyn Directory

Retirement Reality Check, with Michael Sheldon #256

Release Date: 06/03/2025

Five Reasons a Brokerage Account Might Be Better Than an Annuity for Your Investments, #260

Retire With Ryan

I’m exploring a common dilemma for anyone coming into a lump sum of money, whether from an inheritance, the sale of a business, or another windfall: Should you invest in a traditional brokerage account or opt for an annuity? On this week's episode, I discuss the key differences between annuities and brokerage accounts, highlighting the five major pitfalls of annuities that are often overlooked. You'll learn why transparency, flexibility, and tax efficiency make brokerage accounts a better fit for many investors, especially those seeking to beat inflation and maintain control of their funds....

Facts vs. Fiction in Retirement Planning, #259

Retire With Ryan

From the truths about making large purchases in retirement to whether you really need to pay off your mortgage before you stop working, I’m sharing years of financial expertise to challenge a few retirement myths so you can make balanced, informed decisions. We’re talking strategies for charitable giving, clearing up misconceptions about reverse mortgages, and explaining why inflation may be your biggest risk in retirement. If you’re looking for practical advice on enjoying your savings while still planning for the long run, or if you want to protect yourself from financial scams...

Seven Smart Reasons to Leave Your Old 401(k) with a Previous Employer, #258

Retire With Ryan

Building on last week’s discussion about why rolling over your old 401(k) into an IRA could be a smart move, this episode flips the script. It explores seven compelling reasons you might want to leave your 401(k) with your previous employer instead. I break down factors like fees, company stock advantages, penalty-free withdrawals, legal protections, and unique investment options that could all influence your decision. If you're approaching retirement or just planning your next career move, this episode is packed with insights to help you make the best choices for your financial...

Five Reasons to Roll Over Your Old 401k into an IRA, #257

Retire With Ryan

In today's episode, I’m diving into a topic that’s top-of-mind for anyone who’s switched jobs: what should you do with your old 401(k) plan? I discuss five key reasons why moving them into an IRA could simplify your financial life, from consolidating accounts for better control to gaining access to a broader range of investment options, reducing fees, optimizing Roth and after-tax funds, and making it easier to work with a financial advisor. Whether you’re planning your next career step or just want to make your retirement savings work harder for you, this episode is packed with...

Retirement Reality Check, with Michael Sheldon #256

Retire With Ryan

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...

Breaking Down the FERS Retirement System for Federal Employees, #255

Retire With Ryan

On this week’s episode, I’m discussing the Federal Employees Retirement System, or FERS, a program that covers nearly all civilian federal workers. If you’re a federal employee curious about when you’re eligible to retire, how your pension is calculated, what the Thrift Savings Plan offers, or how special early retirement and survivor benefits work, this episode is your go-to resource. We’re breaking down the three key components of FERS: your Basic Benefit Plan (a pension), Social Security, and the Thrift Savings Plan, as well as important details like cost-of-living...

Four Costly Mistakes to Avoid When Claiming Social Security While Working After 65, #254

Retire With Ryan

Thinking about collecting Social Security while you’re still working? It’s a tempting option, but there are several crucial mistakes you’ll want to avoid. Using real-life stories, I’m laying out the four big pitfalls, like earning over the social security limit, jeopardizing your health savings account, mishandling Medicare enrollment, and forgetting about tax withholding. These missteps can lead to unnecessary penalties, and so I want to give some actionable strategies to help you make the most of your benefits without unpleasant surprises. You will want to hear this episode if...

Applying Warren Buffett’s Investment Wisdom to Your Life, #253

Retire With Ryan

It’s been announced that Warren Buffett is stepping down as CEO of Berkshire Hathaway. In this episode, I’ll discuss Buffett’s humble beginnings, his approach to investing, and the philosophy that built one of the most successful companies in history. I’ll also break down Warren Buffett’s wisdom into seven powerful, practical tips that align with my own approach to advising clients. Listen for tips on starting your investment journey early, staying the course during tough markets, and prioritizing temperament over intellect. You will want to hear this episode if you are...

Top Five HSA Mistakes That Are Costing You Money and How to Avoid Them, #252

Retire With Ryan

On the show today, I’m discussing something that could be a game-changer for your retirement savings: Health Savings Accounts, or HSAs. If you’re on a high deductible health plan, you might be eligible for this unique, triple tax-free account, but are you making the most of it? I’m sharing the top five mistakes people make with their HSA accounts. If not avoided, those mistakes can cost you serious money and limit your financial options later in life. I’m covering everything from choosing the right HSA provider to maximizing your investments within the account, tracking expenses, and...

Six Dave Ramsey Tips That Could Hurt Your Retirement Plan, #251

Retire With Ryan

Radio personality Dave Ramsey is a huge name in the personal finance niche. While he’s celebrated for helping countless listeners take control of their finances, many of his recommendations have sparked debate within the financial planning community. I’m going to break down six of the most controversial opinions promoted by Ramsey, including advice on retirement withdrawals, debt payoff strategies, Roth accounts, investing approaches, mortgages, and the use of credit cards. I will also weigh up the pros and cons of Ramsey’s methods, highlighting where they might help and where they...

More Episodes

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.