Cleaning Up Your Finances Before Retirement Arrives

When was the last time you “cleaned up” your retirement plan instead of your inbox? In this episode, Jason Bergey explains why simplifying your portfolio, eliminating duplicate holdings, and organizing accounts can reduce confusion and improve clarity as retirement approaches. The conversation high…

Preparing for Retirement Before It’s Forced on You

Planning to work longer doesn’t always mean you’ll get the chance. In this episode, Jason Bergey explains why nearly half of recent retirees left the workforce earlier than expected—and how health issues, layoffs, or caregiving can quickly change even the best‑laid plans. The conversation explores …

Why Your “Moderate” Portfolio May Be Riskier Than You Think

Ignoring rebalancing can quietly turn a retirement portfolio into a much bigger risk than you realize. In this episode, Jason Bergey explains why many near‑retirees never rebalance their accounts—and how that oversight can magnify risk just as income becomes crucial. The discussion covers rebalanci…

Best Of: Are You Really Ready? The Retirement Checklist for 2026

A new $6,000 senior deduction is just the start—retirement tax planning in 2026 is more complex (and more important) than ever. In this episode, Jason Bergey explains why tax planning isn’t just for April, how the “one big, beautiful bill” changes the game, and why your biggest retirement expense m…

The Tax Traps That Catch Retirees by Surprise

Getting hit with a tax bill in retirement usually isn’t bad luck—it’s lack of planning. In this episode, Jason Bergey explains why many retirees are surprised by taxes on Social Security, IRAs, and income timing, even after decades of saving. The discussion breaks down the difference between simply…

Best Of: The End of One-Size-Fits-All Advice

Old rules of thumb like the 4% withdrawal rate and retiring at 65 are fading fast as retirees face longer lives, rising healthcare costs, and unpredictable markets. In this episode, Jason Bergey explains why it’s time to rethink outdated strategies and focus on a plan tailored to your real needs. L…

Why AI Advice Can Miss the Mark in Retirement

Free financial advice from AI might sound tempting—but it can quietly create bigger problems near retirement. In this episode, Jason Bergey discusses why relying on headlines, market noise, or computer‑generated guidance can lead to costly missteps. The conversation covers inflation, healthcare cos…

Why Headline‑Driven Decisions Can Hurt Retirement

When headlines get loud, emotional decisions can quietly derail retirement plans. In this episode, Jason Bergey discusses how reacting to market volatility, geopolitical conflict, and oil‑driven inflation often leads to costly mistakes—especially for those nearing retirement. The conversation explo…

Why You Know Your Bracket Better Than Your Retirement

If you spend more time filling out a March Madness bracket than reviewing your retirement plan, you’re not alone—but that imbalance can matter. In this episode, Jason Bergey uses bracket season as a lens to discuss why many people obsess over short‑term competitions while ignoring long‑term financi…

Retiring Solo: The Challenges No One Talks About

Retirement planning looks very different when you’re doing it on your own. In this episode, Jason Bergey discusses the unique challenges facing solo retirees, from managing liquidity and healthcare risks to making Social Security and withdrawal decisions without a spouse to lean on. The conversatio…