The Retirement Planning Mistake Gen X Can’t Afford

A golf cart might reveal more about retirement planning than you think. Amy Ross explains how she reverse-engineers retirement plans to uncover hidden risks, reviews the benefits of annuities and Roth conversions, and discusses why many Gen X workers are unprepared for retirement. Amy also explores…

The Truth About Annuities in Retirement

Annuities can be powerful—or misunderstood—depending on how they’re used. Amy Ross breaks down how these tools fit into retirement planning, from income generation to principal protection. The conversation focuses on balancing growth, safety, and flexibility while avoiding common mistakes that limi…

Lessons on Work Ethic and Wealth Building

A behind-the-scenes experience sparks a broader conversation about work ethic, opportunity, and financial success. Amy Ross reflects on leadership lessons, discipline, and the evolving definition of the American Dream, connecting those ideas to retirement planning and long-term financial independen…

The 3 Questions That Reveal If You’re Really Ready to Retire

Are you planning your next vacation more carefully than your entire retirement? Amy Ross breaks down why so many people prioritize short-term spending over long-term financial clarity and how that disconnect shows up in real life. She explores the three core questions of retirement—income, expenses…

What a Full Body Scan Reveals About Your Finances

What would a “full body scan” of your retirement plan reveal? This episode with Amy Ross uncovers how analyzing your entire financial picture can expose hidden risks, tax inefficiencies, and gaps in income planning. The conversation explores decluttering accounts, aligning investments, and adjustin…

The Retirement Plan That Gives You Confidence

What if retirement planning felt empowering instead of overwhelming? This episode with Amy Ross walks through building income, managing taxes, and preparing for healthcare costs. It also tackles why many don’t want to retire and how understanding your options can reshape the future. Amy Ross and t…

Why More People Are Asking About Annuities

Why are annuities getting more attention—and more questions? This episode with Amy Ross explores shifting attitudes toward annuities, how they fit into retirement planning, and why choosing the right type matters. It also covers advisor relationships and the role of personal guidance. Amy Ross and…

When Financial Planning Meets Family Priorities

What does financial planning look like when family comes first? Amy Ross weaves together conversations about money, memories, and major life moments—from bucket-list experiences to generational goals. The episode reflects on balancing future planning with enjoying life now, and how values shape fin…

The Confidence Gap Between Saving and Spending in Retirement

For many retirees, the challenge isn’t saving—it’s feeling comfortable spending. Amy Ross discusses how reliable income sources, including annuities and structured income strategies, can create clarity and confidence in retirement decisions. The episode explores the idea of “paycheck” and “playchec…

The Retirement Assumptions That Cause Trouble

What happens when retirement planning relies on assumptions instead of structure? Amy Ross explores misconceptions around inheritances, inflation, working longer, and “figuring it out later.” The episode underscores why written plans, realistic timelines, and flexibility matter—especially as career…