

What Retirement Questions Are You Not Asking?
What’s the one retirement question you’re afraid to ask and could the answer change everything? In this episode, Gary Garland explores the questions many retirees never ask, from whether they’re truly on track for retirement to understanding fees, fiduciary responsibilities, investment strategies, …

Why Is Spending Money So Hard After a Lifetime of Saving It?
What if the hardest part of retirement isn’t saving money, but learning how to spend it? In this episode, Gary Garland explores the challenge many retirees face when they transition from decades of accumulating assets to actually using them. He discusses common fears around watching account balance…

Are You Reacting to the Market Like Pavlov’s Dog?
Are your financial decisions being driven by strategy or by emotion? In this episode, Gary Garland uses the concept of Pavlov’s dogs to explain how investor behavior can be triggered by headlines, fear, and hype. The conversation explores why reacting to market noise, timing trends, or following po…

What Does Retirement Really Cost Today?
Is the American Dream still within reach, or is it getting more expensive than ever? In this episode, Gary Garland breaks down the rising cost of life’s biggest milestones, from homeownership to retirement, and why income plays a critical role in financial stability. The conversation explores how r…

What If You Outlive Your Money?
What if living longer is the biggest financial risk you’re not fully prepared for? In this episode of Your Retirement, Your Way, Gary Garland explores how longevity, and the uncertainty around it, can reshape retirement planning. He discusses why lifespan, lifestyle choices, and unexpected health e…

RMDs: The Costly Rule Most Retirees Overlook
What if the biggest tax bill of your life is waiting quietly in your retirement accounts? In this episode of Your Retirement, Your Way, Gary Garland breaks down Required Minimum Distributions (RMDs) and why they can impact far more than just your taxes. He explores how RMDs affect income, tax brack…

What If Social Security Pays Less Than Expected?
The timeline for Social Security shortfalls just moved closer—and that uncertainty has many retirees asking hard questions. In this episode of Your Retirement, Your Way, financial planner Gary Garland unpacks what it could mean if Social Security benefits are reduced sooner than expected. The conve…

Protecting Your Retirement from Fraud and Identity Theft
Fraud is no longer rare—and retirees are increasingly becoming prime targets. In this episode of Your Retirement, Your Way, estate planning attorney and financial advisor Gary Garland discusses how scams are evolving and what individuals can do to protect themselves. From romance scams and imperson…

The Truth About “Secret” Roth Conversion Strategies
Can you really convert to a Roth IRA without paying taxes—or is that a red flag? In this episode of Your Retirement, Your Way, Gary Garland breaks down a MarketWatch question about a so‑called “secret” Roth conversion strategy and explain why claims like these deserve closer scrutiny. The conversat…

Expectation vs. Reality: The Hidden Gaps in Retirement Planning
What if your retirement expectations are “double‑stuffed”—but the reality comes up short? In this episode of Your Retirement, Your Way, Gary Garland unpacks the gap between what retirees expect and what actually shows up, using everything from Oreo math to market returns as real‑world metaphors. He…