Why 37% of Retirees Have Regrets (And How to Avoid Them)
Stay Wealthy Retirement Podcast
Release Date: 06/13/2025
The S&P 500 Trap: Why the "Safe" Choice Is Actually Risky for Retirees
Stay Wealthy Retirement Podcast
"Just buy the index." It’s the simple advice that built your wealth and got you to the finish line. But here’s what often gets overlooked: The strategy that got you to retirement won't necessarily keep you there. When you switch from saving to spending, the math changes. Suddenly, relying on a "simple" S&P 500 strategy exposes you to risks that didn't matter when you had a paycheck. In this episode, we cover: ▶ The Simplicity Trap: Why "decision fatigue" lures smart retirees into risky, overly concentrated portfolios. ▶ S&P 500 Reality Check: Why the "safe" default option is...
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Why Retirees Fear Running Out of Money — Even Though They Rarely Do
Stay Wealthy Retirement Podcast
Everyone fears running out of money in retirement—even millionaires. What most people don’t realize is that research shows most retirees rarely spend down their savings. In fact, many actually see their wealth grow throughout retirement, even during some of the toughest markets in history. In this episode, we unpack: ▶ Why that happens ▶ What the data really says about retirement spending ▶ How to find the right balance between confidence and caution By the end, you’ll see why most retirees worry far more than they need to, and how to feel confident spending your own money....
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The Truth About Long-Term Care Insurance (and When to Buy It)
Stay Wealthy Retirement Podcast
Sales of "traditional" long-term care insurance have fallen 92% since 2002. Meanwhile, hybrid policies have surged to over 500,000 sales a year. But which option actually makes sense for your situation? In this episode, I break down everything you need to know before buying long-term care insurance, including: ▶ The optimal age to purchase ▶ Traditional vs. hybrid policies (the real pros and cons beyond the sales pitch) ▶ The actual costs of proper coverage I'm also sharing three critical implementation details that can make or break your coverage when you need it most. If...
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Long-Term Care: A 5-Step Process to Determine If You Can "Self-Fund"
Stay Wealthy Retirement Podcast
You've heard it before—70% of Americans over 65 will need long-term care. While that number is technically true, it’s also misleading. Because here's what many people don’t realize: the vast majority of retirees will never face a catastrophic, six-figure care event. In fact, nearly two-thirds will spend ZERO out of pocket during their lifetime! 🤯 So how do you prepare responsibly without overpaying for protection you may never use? In this episode, I walk you through a simple 5-step process to decide if you can safely "self-fund" your long-term care needs, while still protecting...
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8 Red Flags You’re About to Get Scammed
Stay Wealthy Retirement Podcast
Americans lost a record $16 billion to scams in 2024—nearly 40% from investment fraud alone. The trend is moving in the wrong direction. In this episode, I share the story of a small-town financial advisor who built trust over decades, until that trust unraveled into one of the most devastating scams they’d ever seen. More importantly, I break down 8 red flags that experts say could indicate you're being conned. Because here’s the truth: falling for a scam doesn’t mean you’re careless or foolish—it means you’re human. And understanding the psychology behind deception is the...
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6 Reasons Why Delaying Social Security Might Hurt Your Retirement
Stay Wealthy Retirement Podcast
Most experts say the smartest Social Security move is to wait until age 70 to claim. On paper, the logic seems simple—delay claiming, and you’ll lock in a larger monthly check for life. But here’s what's interesting: only about 10% of Americans actually wait that long. 🤯 Nearly one-third claim Social Security at 62, and the majority file before full retirement age. So are millions of retirees making a huge mistake… or is the conventional wisdom missing something? In today’s episode, I’m sharing findings from a new research paper showing why delaying until 70 isn’t always...
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7 Signs You’re Closer to Retirement Than You Think
Stay Wealthy Retirement Podcast
We’ve been told our whole lives that retirement happens at 65—maybe 62 if you’re lucky. But in my experience, that traditional timeline isn’t always the reality. In fact, for many people, retirement may be much closer than they realize. After nearly 20 years of building retirement plans, I’ve noticed a recurring theme: Most people overestimate how much they think they need and underestimate how ready they already are. That’s why in this episode, I’m breaking down 7 signs that could mean you’re closer to early retirement than you realize. These aren’t about chasing some...
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Medicare’s Future: Rising Costs, Fewer Perks, and Hidden Traps
Stay Wealthy Retirement Podcast
Even if you’re not on Medicare right now, chances are someone you love is—and sooner or later, you’ll face those decisions yourself. That’s why it’s worth paying attention to an important letter that arrives every September: the Annual Notice of Change. Most people glance at it, toss it aside, and never think twice. But with big shifts coming in 2026, ignoring it could be a costly mistake. And that letter is just the beginning. There are three other Medicare traps that cost people thousands each year and, in some cases, wreck entire retirement plans. In this episode, I’ll walk you...
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Life Insurance Simplified: Smart Strategies for Protecting Your Retirement
Stay Wealthy Retirement Podcast
Despite making insurance decisions almost daily, many retirement savers don't truly understand what they’re buying or why they need it. In today's episode, I'm breaking down life insurance into simple, actionable terms. Specifically, I’m sharing: ‣ The 3 essential steps to managing insurable risks ‣ The key differences between term and permanent life insurance ‣ The exact questions to ask yourself before buying (or hanging onto) any policy I’m also sharing a few little-known facts and tips to help you properly evaluate options you may be considering. Even if you think you...
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How to Avoid Retirement's Biggest Blind Spots Before It's Too Late
Stay Wealthy Retirement Podcast
Retirement is about so much more than money—it's a complete life transition. In this episode, I'm sharing my recent conversation with Adam Cmejla, where we explore the often-overlooked aspects of retirement planning. We discuss: ‣ Why retirement can feel like a grieving process—and how to navigate it ‣ The surprising role responsibility and community play in long-term happiness ‣ Smarter ways to approach Monte Carlo simulations, taxes, and cash management We also share our favorite retirement and investing charts that reinforce the principles essential to keeping financial plans...
info_outline"I planned for 30 years of expenses—but zero years of purpose."
This was a recent client's confession, and she's not alone.
In fact, nearly 40% of retirees say they wish they had waited longer to retire (and it's not about money).
In this episode, I'm revealing why even the most financially prepared retirees fall into identity crises and regret.
I'm also sharing my 5-step "Bridge Strategy" to help you retire with clarity and purpose, not just a seven-figure portfolio.
If you're planning FOR retirement but haven't considered what you're retiring TO, this episode is for you.
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