Retirement Red Flags Podcast

RetirementRedFlags.com

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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. 🚩 Ready for more? Explore our free resources at https://RetirementRedFlags.com.

JAN 22

How to Avoid Losing Generational Wealth

Martin was the kind of retiree most people dream of becoming. Two pensions. Multiple rental properties. Five paid-off vehicles. And a calm, confident outlook that comes from decades of wise financial decisions. At 72, he had everything in order - from Social Security strategy to 529 plans for the grandkids. But when asked how confident he felt about retirement, Martin didn’t say 100%. He said 90%. And that last 10% uncovered a blind spot that even well-prepared retirees often miss: the quiet, devastating threat of losing #generationalwealth.

4 min
JAN 7

Are Annuities a Good Idea in Retirement?

Most people don’t wake up one morning eager to complicate their finances in retirement. They’re usually trying to do the right thing - reduce risk, avoid future tax problems, and make smart decisions with money they’ve spent decades saving. But somewhere between advice meetings, product illustrations, and half-answers, things start to feel more confusing instead of clearer. That’s exactly where Gary found himself.

4 min
12/18/2025

TSP & Taxes in Retirement - The Risk Most Federal Employees Miss

Darcy worked 37 years for the federal government. She saved diligently into her Thrift Savings Plan (TSP), had a pension on the way, and even carried a life insurance policy with cash value. On paper, her retirement looked solid. But when she called with what sounded like a simple question about taxes, it became clear there was a deeper issue at play. Darcy didn’t have a tax problem. She had a clarity problem. And her story, though specific, isn’t rare. It’s a familiar story for many government workers who’ve done everything the system told them to do… and still feel unsure about what retirement actually looks like.

3 min
12/10/2025

An RMD Strategy That Takes the Sting Out of Taxes in Retirement

Most retirees assume the hardest part of planning is saving enough money. But for many - especially those with most of their wealth in pre-tax accounts - the real challenge begins later: taking money out without triggering a tax cascade. That’s exactly what happened to Barb, a sharp, financially capable 61-year-old who had spent decades building a solid nest egg… only to discover that the biggest risks weren’t the ones she expected.

4 min
12/03/2025

Why Saving Enough Might Not Be Enough in Retirement

Even the most diligent planners can find themselves wondering: Are we missing something? That was Jennie. At 66, she was still working full-time but thinking seriously about retirement. Her husband Ron, already semi-retired, still worked here and there and handled most of the investment decisions. Their setup wasn’t in crisis. They weren’t in denial. They were, by all accounts, thoughtful people trying to make smart decisions. But, something just wasn’t sitting right...

4 min
11/26/2025

Avoiding the Financial Advisor Trap & Finding Real Clarity

When one advisor promises 30% returns and another offers “no fees, guaranteed,” it’s no wonder retirees feel like they’re walking through a minefield. We hear it all the time - smart, hard-working retirees feeling more confused with each phone call they get. Everyone wants to pitch something. Everyone seems to have a “better” way. And everyone seems to benefit more than the retiree themselves. This week’s story comes from a listener we’ll call Thomas. He’s a thoughtful, grounded guy in his early 60s who’s done a good job saving for retirement. He’s not the type to jump into anything blindly, and in fact, when we first reached out, he almost hung up. He told us later, “I thought you were just another advisor trying to sell me something.” And honestly? We can’t blame him.

4 min
10/24/2025

Retirement Advice Is Everywhere, But Who Can I Trust?

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.

4 min
10/15/2025

Market Timing in Retirement... When to Pull Back

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.

3 min

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. 🚩 Ready for more? Explore our free resources at https://RetirementRedFlags.com.

Creator

RetirementRedFlags.com
Years Active

2025 - 2026
Episodes

19
Rating

Clean
Copyright

© RetirementRedFlags.com
Show Website

Retirement Red Flags Podcast