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Retirement Red Flags Podcast
Hear firsthand what worked - and what didn’t - for real retirees. Each episode unpacks common mistakes, overlooked risks, and smart strategies to help you retire with confidence.
Listen below or open on Spotify, YouTube, and Apple Podcasts!
Ralph’s Story
Everyone’s got advice for your retirement. The tricky part? Figuring out which advice is actually worth listening to. That’s where Ralph found himself. He had the savings, the advisor, the plan, but something still didn’t sit right with him. Ralph wasn’t in trouble. He wasn’t behind. In fact, after a long and successful career in IT - four decades, a Master’s degree in Computer Science, and most of it spent working from home for AT&T - he’d already retired.
Rich’s Story
You’d think that after 25 years of retirement, the hard questions would be behind you. But for Rich - a 79 year old with a 12% average return over two and a half decades - the most important question is just now coming into focus... Is it time to pull back? This isn’t a story about someone who ran out of money or miscalculated their expenses. It’s a story about someone who did nearly everything right - built his own business, sold it, rode through the 2008 crash, and stayed aggressive enough to beat the market in most years since.
Brian’s Story
What if you did everything right? Saved early. Built up millions. Played by the rules. Stayed disciplined. And then one day - after all the years of careful planning - you realize the real cost doesn’t show up while you’re working. It shows up the moment you stop. This is Brian’s story. Brian is thoughtful. Disciplined. Smart with money. And from the outside, he’s done it all the way retirement planners dream of...
Mike & Lisa’s Story
Saving for retirement is hard enough. But avoiding the tax pitfalls after you've already done the hard work? That's where most people get blindsided. This week’s story comes from a real conversation with a couple we’ll call Mike and Lisa - two thoughtful Midwesterners who had done almost everything right. They’d saved diligently. They weren’t chasing unrealistic returns. They had what most would call a solid plan. And yet... something still didn’t sit right.
Frank’s Story
What if your retirement plan was technically perfect… right up until life happened? You saved consistently. You paid off the house. You timed Social Security just right. You checked every box your advisor told you to check. Then, a $20,000 expense comes out of nowhere, and suddenly you’re wondering if the whole plan still works. It’s not a hypothetical. It’s real... And it happens more often than people think. Recently, we had a call with a retiree who found himself in exactly that position.
Mark’s Story
Retirement should feel like a victory lap. But lately, for people like Mark, it feels more like trying to finish a puzzle where the pieces keep changing shape. Mark’s 67. Still working full-time. On paper, he’s in solid shape. But like many people nearing retirement, Mark has one foot in the spreadsheet and one foot in real life. What he’s not sure about… is the game board. Especially now - with the sweeping legislation called the One Big Beautiful Bill signed into law on July 4th, 2025 - there’s a whole new set of rules, tax codes, and deadlines to keep up with.
Vikram’s Story
You’ve been disciplined for decades. You’ve saved, invested, and stayed the course - but now, with retirement on the horizon, you can’t shake the question: Is this really enough? That’s where Vikram found himself. A smart, forward-thinking software developer with more than two decades in mobile technology and AI, Vikram had been diligent about building his future. He and his wife had set aside over $2 million. He wasn’t starting from scratch - far from it. In fact, his portfolio had consistently delivered 7–10% annual returns. By all measures, things were going well...
Gwen & Harry’s Story
It’s easy to think that if the markets behave and your nest egg is big enough, that your retirement plan is safe. But more and more, we see that the real threat isn’t market risk - it’s taxes - especially when multiple income streams pile onto one return. Take Gwendolyn. She’s in her 70s, living in Florida, steady and smart. While juggling her husband’s therapy appointments, she still approaches her finances with precision. Her focus wasn’t on chasing strategies, but on keeping things “tidy.” That word carried more weight than she realized.
Don's Story
Some retirees spend 50 years working and saving… only to discover that the real threat to their retirement isn’t the stock market - it’s the tax bill hiding in plain sight. That’s exactly what happened to “Don Barrett,” a newly retired engineer in the Catskills who spent more than five decades manufacturing military-grade fans, the kind that cost more than most high-end laptops. Don’s work ethic was unmatched. He was careful, disciplined, and the kind of man who never took a financial shortcut.
Mary Ann's Story
Imagine standing in the middle of a life transition - grieving, exhausted - and realizing you’re suddenly in charge of someone else’s financial legacy? That was Mary Ann. Not her real name, but a very real story. A lifelong educator who could color-code a school year with her eyes closed… and still felt lost when her father died and the paperwork landed in her lap. When doctors missed key markers, complications piled up and his life ended sooner than anyone expected.
John's Story
Meet John. He had a pension, a traditional 401(k), a few IRAs, and Social Security coming in. By all conventional measures, he was doing just fine. But when we asked him how confident he felt in his retirement plan - on a scale from 0 to 100 - he didn’t even pause. “Forty-five,” he said. “I’ve got the pieces. I just don’t know if they work together.” This wasn’t fear. This was something more unnerving: uncertainty in the face of a life that was supposed to feel settled.
Ray's Story
Ray didn’t call in a panic. He wasn’t on the brink of bankruptcy. He wasn’t even looking for a big change. He was just... tired. Tired of the ads, the jargon, the endless promises about “retirement made simple” - and the sneaking suspicion that nobody was really saying anything of substance. And now, in his seventies, with his health starting to fade and a move to New Jersey on the horizon, he’s left holding a handful of retirement accounts - and very few answers.
Dr. Melissa Harper's Story
Meet Melissa. She retired earlier this year after decades in pharmaceutical research. She had the kind of career most people would envy - smart decisions, steady savings, and a methodical mindset built on years of working in science. Melissa lived by the data. Every major decision in her life was backed by research, precision, and patience. So when she retired, she didn’t expect to feel... unsure.
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