Why Retirement Still Feels Stressful—Even With Millions

Why do some retirees with millions still feel anxious about spending their money? In this episode, Jon Hicks explores the psychological shift from saving to using retirement funds and why it can be harder than expected. The discussion highlights how fear, habits, and uncertainty can impact decision…

When Waiting Costs More Than You Think

What if chasing the “perfect” financial decision costs you the moments that matter most? In this episode from this past weekend’s radio show, Jon Hicks explores how retirement planning goes beyond spreadsheets and projections. From Social Security timing decisions to the risks of over-saving or del…

Why Your Next Market Reaction May Surprise You

Will you react any differently the next time the market drops? This episode explores how investor behavior is often driven more by emotion than logic, especially as retirement approaches. Jon Hicks breaks down why past reactions to market downturns tend to repeat—and how discipline, planning, and u…

The Tax Mistakes That Could Follow You Into Retirement

Are hidden tax traps quietly reshaping your retirement? This episode from this past weekend’s radio show explores how retirement shifts you from taxpayer to tax manager—and why decisions around withdrawals, Social Security, and account types can affect long-term outcomes. Jon Hicks breaks down comm…

Roth vs. Pre-Tax: Are You Choosing the Right Strate

Should all your retirement savings go into Roth—or is that strategy missing the bigger picture? In this episode, Jon Hicks breaks down the debate between Roth and pre-tax 401(k) contributions, explaining why flexibility—not extremes—can play a key role in retirement planning. He explores how differ…

Sell in May? Why This Popular Strategy Is Being Questioned

“Sell in May and go away” might sound catchy—but does it still hold up? In this episode, Jon Hicks breaks down the origins of this long-standing market saying and why its relevance is being questioned today. He explores how relying on simple investment rules can miss the bigger picture, especially …

The Retirement Mindset Most People Miss

Retirement isn’t just about saving—it’s about what your money can actually do next. In this episode from this past weekend’s radio show, Jon Hicks explores the shift from growing wealth to using it with purpose. He discusses why many retirees focus too narrowly on preservation, how income, taxes, a…

The First Year of Retirement Could Change Everything

What if the first year of retirement has more impact than the next 20 combined? In this episode, Jon Hicks breaks down sequence of returns risk and why early market downturns can significantly affect long-term outcomes. Using real-life examples, he explains how timing—not just performance—can shape…

From Blurry to Clear: Rethinking Your Retirement Plan

What happens when retirement shifts from a blurry idea to a clear plan you can actually follow? In this episode from this past weekend’s radio show, Jon Hicks explains why retirement planning is about more than numbers—it’s about turning savings into a lifestyle. He breaks down sequence of returns …

When Market Volatility Isn’t the Real Problem

When headlines scream chaos, it’s easy to assume volatility is the enemy—but that thinking can be misleading. In this episode, Jon Hicks discusses how economic shocks, rising oil prices, and nonstop news cycles affect retirement planning and investment decisions. The conversation explores why volat…