Retirement Roundtable

Could you really live to 100—and if so, are you ready for it? This episode explores the three essential questions every retiree must ask: Can I afford a longer life? Who will I share it with? And how will I find purpose in my golden years? Join John Scallan as he breaks down the strategies, stories, and real-life lessons for thriving in a century-long retirement. For more information, please...

What happens when retirement planning collides with the complexities of “grey divorce” and legacy concerns? This episode with John Scallan dives into real-life stories, including a surprising call from an ex-spouse worried about a seven-figure 401(k), and explores how couples—and families—navigate risk, income, and communication in retirement. Discover strategies for aligni...

What if winning the lottery or retiring early isn’t the answer you think it is? This episode with John Scallan explores the realities behind sudden wealth, risk tolerance, and the difference between financial advice and self-management. Discover why purpose matters as much as money, and how asking the right questions can shape your retirement journey. For more information, please visit www....

What’s more uncomfortable—talking about family finances or losing half your inheritance to taxes? In this episode, John Scallan tackles the largest wealth transfer in U.S. history, the truth about Social Security taxes, and why 2025 may be your golden window for Roth conversions. With practical advice on initiating tough family conversations and maximizing tax strategies, this episode...

What if your retirement plan got less attention than your vacation itinerary? In this episode, John Scallan challenges listeners to rethink their financial priorities, offering insights on bond risks, Social Security uncertainty, and the value of a second opinion. From short-term bond strategies to advisor red flags, the conversation is packed with practical advice for building a flexible, respons...

What if living too long became your biggest financial fear? In this episode of the Retirement Roundtable, John Scallan breaks down three powerful tools to turn your savings into lifetime income—no matter how long you live. From MIGAs to FIAs with income riders, learn how to build your own pension and protect against market downturns while keeping liquidity for emergencies. Whether you're nea...

What if one dollar could cost you thousands in retirement? In this episode of  Retirement Roundtable , John Scallan tackles the emotional side of financial planning and the real risks retirees face—from Social Security cuts to the hidden Medicare surcharge known as IRMAA. He breaks down urgent tax-saving opportunities for those aged 60–63 and explains why planning five years ahead...

Think you’ve got time to plan for retirement? Think again. In this episode, John Scallan breaks down how procrastination, hidden 401(k) fees, and misunderstood annuities can quietly sabotage your financial future. From time optimists to costly investment missteps, learn why waiting could cost you thousands—and how to take action now. Whether you're just starting or already retired, thi...

What if outdated fears are keeping you from the best retirement tools available today? In this episode, John Scallan breaks down the evolution of annuities, the role of index funds, and why guaranteed income is more critical than ever. From the “golden age of annuities” to dynamic income strategies that span 30+ years, this conversation is packed with practical insights for anyone appr...

Can timing the market really beat a smart plan? In this episode, John Scallan breaks down why chasing perfect moments can cost you—and how strategic models can protect your retirement. From Roth conversions to hidden costs like healthcare and family emergencies, John shares actionable insights to help you preserve assets and build income. Plus, hear thoughts on financial expert Ed Slott, inh...

What if your biggest retirement mistake was trying to time the market? In this episode, John Scallan of Cypress Financial breaks down why emotional investing can cost you—and how strategic planning can save you. From Roth IRA conversions and inherited wealth to hidden retirement costs like healthcare and taxes, John shares practical advice for building income that lasts. Plus, a reminder tha...

What’s worse than running out of money in retirement? Regretting the life you didn’t live. In this episode, John Scallan explores how to balance smart saving with guilt-free spending—so you don’t end up like Agnes, who saved every penny but missed out on life. From bucket list dreams to bond strategies and hidden fees, he covers how to plan with purpose, protect your future...

This week on The Retirement Roundtable, John Scallan discusses the critical importance of planning for retirement, emphasizing that many people spend more time planning vacations than their financial futures. He addresses the current economic climate, including the national debt and its implications for investment strategies, particularly regarding bonds. The conversation also covers the uncertain...

This week on The Retirement Roundtable, John Scallan discusses the various roles of financial advisors, including wealth managers and income planners, and emphasizes the importance of income in retirement. He addresses common misconceptions about retirement savings targets, the complexities of taxes in retirement, and highlights frequent mistakes people make in their retirement planning. The conve...

In this episode of The Retirement Round Table, John Scallan discusses various aspects of retirement planning, including the importance of stress testing financial portfolios, navigating market volatility, and building reliable income strategies. He emphasizes the need for modern financial tools and the dangers of outdated strategies, providing listeners with insights on how to effectively prepare...

In this episode of The Retirement Roundtable, John Scallan discusses the various fears that individuals face as they approach and navigate retirement. The conversation covers the fear of running out of money, concerns about social security, the impact of taxes, healthcare costs, and the identity crisis that can occur post-retirement. John emphasizes the importance of having a solid financial plan...

This week, John Scallan discusses critical aspects of retirement planning, including the implications of Roth conversions, the importance of understanding Social Security benefits, and the necessity of mid-year portfolio reviews. He emphasizes the urgency of making informed financial decisions amidst changing tax laws and the impact of hidden investment fees on long-term wealth accumulation. The c...

In this episode of The Retirement Roundtable, John Scallan discusses the various roles of financial advisors, the importance of income in retirement, and the misconceptions surrounding annuities. He emphasizes that retirement planning is not just about hitting a target savings number but about creating a personalized income strategy. The conversation also covers the impact of taxes on retirement i...

This week, John Scallan discusses the current market volatility and its implications for retirement planning. He emphasizes the importance of having a robust retirement plan that can withstand economic downturns, rather than trying to predict market movements. The conversation also covers the significance of Required Minimum Distributions (RMDs) and the flexibility in scheduling them, as well as s...

In this episode of The Retirement Round Table, John Scallan discusses the nuanced differences between being rich and being wealthy, emphasizing the emotional aspects of financial well-being. He explores the importance of supporting family dreams without jeopardizing retirement security, and offers practical budgeting advice for couples. The conversation also touches on planning for retirement expe...

In this episode of The Retirement Round Table, John Scallan discusses the critical role of income in retirement, particularly through annuities. He addresses common misconceptions about annuities, emphasizing their importance in providing financial security against longevity risk. The conversation also explores the reasons behind financial procrastination and the challenges of DIY retirement plann...

This week, John Scallan discusses the current state of the economy, market volatility, and its implications for retirement planning. He emphasizes the importance of having a solid retirement plan that can withstand economic downturns, rather than trying to predict market movements. The conversation also covers the complexities of Required Minimum Distributions (RMDs) and the strategic timing of So...

This week, John Scallan discusses the current state of the bond market and its implications for retirement savers. He emphasizes the importance of understanding the risks associated with bonds, especially in a rising interest rate environment. The conversation also covers the limitations of the traditional 4% withdrawal rule for retirement income, advocating for a more personalized approach to inc...

This week on The Retirement Roundtable, John Scallan discusses the impact of market volatility on retirement planning, the importance of emotional and financial readiness for retirement, and the nuances of annuities as a source of retirement income. He emphasizes the need for a personalized approach to investment strategies, particularly as individuals approach retirement age, and highlights the s...

In this episode of The Retirement Roundtable, John Scallan discusses the evolving landscape of retirement planning, emphasizing the importance of preparing for longer lifespans. With advancements in healthcare, individuals may need to plan for 30 to 40 years of retirement income. The conversation covers critical questions about financial security, the role of caregivers, the dynamics of couples in...