Podcast Episodes

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!

Spotify Apple Podcasts YouTube

All episodes, newest first

Episode 19 artwork: How to Avoid Losing Generational Wealth, Real Retiree Stories: Martin's Story, with a portrait of a smiling older man with glasses.

Episode 19: 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 generational wealth.

Listen Now: Episode 19
Episode 18 artwork: Are Annuities a Good Idea in Retirement?, Real Retiree Stories: Gary's Story, with a portrait of a smiling older man.

Episode 18: 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.

Listen Now: Episode 18
Episode 17 artwork: TSP & Taxes - The Risk Most Federal Employees Miss, Real Retiree Stories: Darcy's Story, with a portrait of a smiling older woman with glasses.

Episode 17: TSP & Taxes - 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.

Listen Now: Episode 17
Episode 16 artwork: An RMD Strategy That Takes the Sting Out of Taxes, Real Retiree Stories: Barb's Story, with a portrait of a smiling older woman.

Episode 16: An RMD Strategy That Takes the Sting Out of Taxes

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.

Listen Now: Episode 16
Episode 15 artwork: Why ‘Saving Enough’ Might Not Be Enough in Retirement, Real Retiree Stories: Jennie M.'s Story, with a portrait of a smiling older woman with curly white hair.

Episode 15: 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...

Listen Now: Episode 15
Episode 14 artwork: Avoiding the Advisor Trap & Finding Real Clarity, Real Retiree Stories: Thomas' Story, with a portrait of a smiling older man with a gray beard.

Episode 14: Avoiding the 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.

Listen Now: Episode 14
Episode 13 artwork: Retirement Advice Is Everywhere, But Who Can I Trust?, Real Retiree Stories: Ralph's Story, with a portrait of an older man with glasses sitting at a laptop.

Episode 13: 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.

Listen Now: Episode 13
Episode 12 artwork: Market Timing in Retirement... When to Pull Back, Real Retiree Stories: Rich's Story, with a portrait of a smiling older man in a green sweater.

Episode 12: 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.

Listen Now: Episode 12
Episode 11 artwork: Planning for IRA Withdrawals in Retirement, Real Retiree Stories: Brian's Story, with a portrait of a smiling man with glasses resting his chin on his hands.

Episode 11: Planning for IRA Withdrawals in Retirement

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...

Listen Now: Episode 11
Episode 10 artwork: Tax-Free Retirement Income... Here’s How They Did It, Real Retiree Stories: Mike & Lisa's Story, with a portrait of a smiling couple, the woman riding piggyback on the man.

Episode 10: Tax-Free Retirement Income... Here’s How They Did It

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.

Listen Now: Episode 10
Episode 9 artwork: A Retirement Tax Strategy That Can Cover Surprise Costs, Real Retiree Stories: Frank's Story, with a portrait of a smiling older man giving a thumbs-up.

Episode 9: A Retirement Tax Strategy That Can Cover Surprise Costs

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.

Listen Now: Episode 9
Episode 8 artwork: One Big Beautiful Bill & One Big Retirement Question, Real Retiree Stories: Mark's Story, with a portrait of a smiling older man in a suit jacket.

Episode 8: One Big Beautiful Bill & One Big Retirement Question

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.

Listen Now: Episode 8
Episode 7 artwork: How to Prepare for Retirement in Your Final Working Years, Real Retiree Stories: Vikram's Story, with a portrait of a smiling older man.

Episode 7: How to Prepare for Retirement in Your Final Working Years

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...

Listen Now: Episode 7
Episode 6 artwork: Map Your Income, Save Your Sanity, Real Retiree Stories: Gwen & Harry’s Story, with a portrait of an older couple smiling together.

Episode 6: Map Your Income, Save Your Sanity

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.

Listen Now: Episode 6
Episode 5 artwork: Why RMDs Matter More Than Market Crashes, Real Retiree Stories: Don's Story, with a portrait of a smiling man with glasses.

Episode 5: Why RMDs Matter More Than Market Crashes

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.

Listen Now: Episode 5
Episode 4 artwork: When Life Hands You the Financial Junk Drawer, Real Retiree Stories: Mary Ann's Story, with a portrait of a smiling woman with long gray hair.

Episode 4: When Life Hands You the Financial Junk Drawer

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.

Listen Now: Episode 4
Episode 3 artwork: The Missing Variable in Your Retirement Plan, Real Retiree Stories: John's Story, with a portrait of a smiling older man in a blazer.

Episode 3: The Missing Variable in Your Retirement Plan

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.

Listen Now: Episode 3
Episode 2 artwork: When Retirement Still Feels Like a Question Mark, Real Retiree Stories: Ray's Story, with a portrait of a smiling older man with a white beard.

Episode 2: When Retirement Still Feels Like a Question Mark

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.

Listen Now: Episode 2
Episode 1 artwork: I Did Everything Right... So Why Do I Still Feel Unsure?, Real Retiree Stories: Dr. Melissa Harper's Story, with a portrait of a smiling woman adjusting her glasses.

Episode 1: I Did Everything Right... So Why Do I Still Feel Unsure?

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.

Listen Now: Episode 1

Are You Ready For Retirement?

The 2026 Retirement Checklist

A 5-minute checklist to uncover hidden risks that could shrink income, increase taxes, or erode your legacy.

Get the Free Checklist

Red Flag Review

A complimentary, personalized review designed to uncover your blind spots before they become problems.

Request Your Review