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Tax Return Red Flags

Retirement Starts Today

Release Date: 03/09/2026

The Four Risks to Retirement Security show art The Four Risks to Retirement Security

Retirement Starts Today

Chris Heye makes the case in a Journal of Financial Planning article that the two retirement risks we obsess over might not be the two most likely to derail us. There are four risks in play, and the two nobody models are the ones quietly doing the most damage: Longevity Risk Market Risk Health Risk Decision Risk I go into depth on those last two. In our Listener Question, a 69-year-old retired engineer and do-it-yourselfer asks about setting up my plan for his wife who's just not into dollars and cents. And in our Retire To Something segment: Debbie shares her "One Year Sabbatical" — and...

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How Much Should You Worry About Inflation? show art How Much Should You Worry About Inflation?

Retirement Starts Today

Inflation again? Christine Benz over at Morningstar has three questions that tell you exactly how exposed you are - and how much retirees worry about inflation. Then, a listener question from someone one year into retirement who says their pension check feels like it just shrank ten percent - and what they might do to remedy that.  And in our Retire To Something segment, Linda from Ontario, Canada, wanted a job at a cheese shop that wasn't hiring — and she applied anyway. Resources: Morningstar article by Christine Benz: Christine Benz book:   Connect with Benjamin Brandt: ...

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Revisiting the 4% Rule, with Bill Bengen show art Revisiting the 4% Rule, with Bill Bengen

Retirement Starts Today

If you've been anywhere close to a retirement podcast over the last 10-20 years, you've heard of the 4% rule. And like many people, you might have questions about it. We're going to hear about it directly from the horse's mouth as we talk to Bill Bengen, who first articulated the 4% withdrawal rate as a rule of thumb for withdrawal rates from retirement accounts. The 4% rule is not a rigid rule but a guideline. Its application requires careful consideration of individual factors, including health, life expectancy, and specific financial circumstances. Bengen encourages retirees to tailor their...

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Retirement Is a Sprint, Not a Marathon show art Retirement Is a Sprint, Not a Marathon

Retirement Starts Today

Fritz Gilbert says the adage that "Retirement is a marathon, not a sprint" is backwards. He cites an average age where health starts to decline is 64, so sprinting in those first few years when the average retiree is 61-63 makes sense. We will dig into that idea, then follow it up with a listener who can't get her husband to think about anything but saving money.   Resource: Article by Fritz Gilbert:   Connect with Benjamin Brandt: Subscribe to the This Week in Retirement: Get the Retire-Ready Toolkit: Work with Benjamin:  Get the book! Follow Retirement Starts Today in:,...

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Is Your Cautious Retirement Spending Doing More Harm Than Good? show art Is Your Cautious Retirement Spending Doing More Harm Than Good?

Retirement Starts Today

The fear of running out of money in retirement turns out to be mostly backwards. For super-savers, the data says the opposite usually happens. A piece from Danielle Labotka at Morningstar makes the case that for a lot of retirees: Being too cautious with your spending is actually the bigger risk.  In our listener question segment: Anonymous wants to give money to her kids with warm hands, not cold. How much you can safely give today without putting your own retirement at risk? And then we'll wrap up with our Retire To Something segment: Dabbling in a little of everything. Resources: ...

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The IRS Penalty Retirees Never See Coming (And How to Beat It) show art The IRS Penalty Retirees Never See Coming (And How to Beat It)

Retirement Starts Today

Every year, thousands of retirees pay an extra penalty to the IRS — and almost none of them see it coming. What catches them off guard isn’t a penalty for owing too much. You can do everything right — claim Social Security at the right age, run picture-perfect Roth conversions, manage your withdrawals down to the dollar — and still get a letter from the IRS charging you extra. I reworked a framework from an article by Sheryl Rowling at Morningstar into four clean, completely legal ways to avoid getting tax penalties. After that, we’ve got a listener question: A retiree writes in and...

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Consumer Sentiment is Terrible show art Consumer Sentiment is Terrible

Retirement Starts Today

Americans don't feel great about the economy. Consumer Sentiment just hit the lowest reading in roughly 75 years. Ben Carlson over at A Wealth of Common Sense dug into why that might be, and what it means for those of us trying to enjoy a retirement when it always feels like the second shoe is about to drop. In our Listener Question segment, we hear from someone who is sitting on 50x their annual spending - and they can't get their spouse to spend it. Wrapping up the episode we hear from Karen in our "Retire To Something" segment. She's thru-hiking thousands of miles and loving it. Resource: ...

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The IRA Decision That Affects Your Kids show art The IRA Decision That Affects Your Kids

Retirement Starts Today

There's a decision your surviving spouse is going to make about your IRA, after you're already gone, that can either cut short or stretch out how long your kids get to keep that money growing — and most people don't even realize the choice is being made. We're going to zero in on one option in particular, one that sounds a little crazy on its face: turning down an inheritance on purpose.  In our Listener Question segment: A listener wrote in about a family farm, a couple of brothers he'd rather not be in business with, and whether saying "no thank you" to his own share is the way to...

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The Richest Person in the Graveyard show art The Richest Person in the Graveyard

Retirement Starts Today

You've heard it said a hundred times: Spend the money, make the memories, don't die with regret.  However, for certain kinds of retirees, dying as the richest person in the graveyard isn't a tragedy at all. The comfort of simply having the money can be worth more than anything you'd ever buy with it.   Today, we begin with an article, The Many Utilities of Retirement, which talks about RPIG (the Richest Person In the Graveyard) versus FORO (the Fear of Running Out of money). It's an interesting look at the juxtaposition. After that, a question - listener that calls himself the...

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The Best Strategies for Boosting Starting Withdrawal Rates in Retirement show art The Best Strategies for Boosting Starting Withdrawal Rates in Retirement

Retirement Starts Today

If you want to spend more at the beginning of retirement, which withdrawal strategies actually let you do that? This week's Retirement Headline from Amy C. Arnott called "The Best Strategies for Boosting Starting Withdrawal Rates in Retirement" answers that question. For our Listener Question: A listener wrote in wondering whether sequence-of-returns risk really fades away after the first decade of retirement, and if so — whether that means it's safe to bump withdrawals up to 5.5% or more later in the game. And we wrap it up with another Retire To Something segment. Resource: Article by Amy...

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More Episodes

Sheryl Rowling positions income tax returns as diagnostic tools — not merely a compliance document — and outlines four common red flags that suggest a client failed to take advantage of proactive tax strategies.

Here are "4 Tax Return Red Flags That Signal Poor Tax Planning":

  1. Very Low or Zero Taxable Income
  2. Charitable Giving After Age 70½ Without Using QCDs
  3. Donating Cash Instead of Appreciated Securities
  4. Holding Municipal Bonds in Low Tax Brackets

For our listener question: "I'm in a job I hate and would love to scale back to something that could pay less but be more enjoyable -- how can I evaluate if that is possible?". Most people think the first question is: “How much do I have saved?”, but that's actually backwards. I share a calculation for cash burn that matters more than your portfolio balance.

And to wrap up the show in our "Retire to Something" segment, I’ll share Jerry's story that shows us how retirement isn’t about winding down — it’s about doubling down on growth, adventure, and intentionally building an active, meaningful life. 

 

Resource:
Article by Sheryl Rowling on Morningstar: 4 Tax Return Red Flags That Signal Poor Tax Planning

 

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