Retirement Starts Today Radio

Retirement Starts Today Radio

Do you want to spend more money in retirement, while paying less taxes? Great news, you're in the right place! I'll also teach you the benefits of retiring TO something, while most retirees only solve half the equation by retiring FROM something. Tune in every Monday morning - hosted by Benjamin Brandt CFP, RICP. Join my "Every Day is Saturday" weekly newsletter for show notes, free book giveaways and other great retirement content: www.retirementstartstodayradio.com/newsletter

Episodes

April 20, 2026 15 mins

Why is it so hard to spend the money you spent a lifetime saving?

This is a question from Janet Bodnar in a Kiplinger article. She admits that one of her guilty pleasures in retirement is treating herself to a casual lunch while she's out running errands. Why does she feel so guilty?

Christine Benz from Morningstar is quoted in the article, which we discuss at length in this episode.

Then a listener asks a question I think a lot of...

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Your beneficiary designations are probably outdated. Not because you made bad decisions, but because you made them once and never looked again. We're going to walk through five areas where these forms commonly go wrong, and what you can do about it. 

For our Listener Questions segment: "What's the best way to position any assets I have for when my wife and I pass — to most easily and efficiently pass on to our kids?"

And this week'...

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How do higher oil prices impact stock market returns? Ben Carlson at A Wealth of Common Sense challenges the assumption most people have, but with some genuinely surprising and con historical data.

For those who retired right around 2022, our Listener Questions segment might interest you. A listener is comparing bonds to guaranteed products like MYGAs and annuities with income riders. They're seeing five and a half to six percent g...

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What if you paid all your taxes - and still got hit with a penalty from the IRS? 

Our retirement headline this week comes from Laura Saunders in the Wall Street Journal. Estimated tax penalties are skyrocketing, and retirees and investors are some of the most likely to get caught in the trap.

We will cover that, then hop into our Listen Question: "What happens when you lose faith in fixed income as the foundation for your retiremen...

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March 23, 2026 16 mins

Some desirable investment income - like interest and dividends - might actually hurt high-net-worth investors' bottom line. This comes from an article by Larry Swedroe in Financial Advisor Magazine.

He outlines four hidden costs that can quietly erode over 1% of after-tax returns each year:

  • Cash Drag
  • Tax Deferral
  • Step-up and Charitable Giving Advantage
  • Financial Planning Flexibility

For our Listener Question: "Are broker...

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You might have received a Social Security cost-of-living increase this year — but did your net check actually go up? 

A recent Wall Street Journal article highlights how rising Medicare premiums and IRMAA surcharges are offsetting those increases for millions of retirees - and "takes a bigger bite out of Social Security checks".

Then, a listener writes in "How to convince my husband's parents to spend their money. We don't need it....

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March 9, 2026 21 mins

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 Bond...
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March 2, 2026 18 mins

Retirees obsess over the exact safe withdrawal rate they think they'll need while simultaneously building layer after layer of backup plans. Dividends, buckets, multiple years of cash, constant Monte Carlo recalculations are all done in the name of safety.

Jordan Grumet's argument to this problem is simple and provocative: If you believe in the safe withdrawal rate, then act like it. Stop stacking contingencies on top of contingenc...

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Sheryl Rowling from Morningstar argues that the greatest danger in retirement isn't the stock market — it's the constant fear of running out of money.

We will walk through her eight "anchors" from the article posted on Morningstar.

Anchor 1: Confirm Your Sustainable Spending Level
Anchor 2: Embrace Flexibility in Down Markets
Anchor 3: Recognize That Spending Often Declines With Age
Anchor 4: Create a Recession Buffer
Anchor 5: Red...

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February 16, 2026 22 mins

What does research say about retirement withdrawal strategies that are specifically designed to leave more money behind? We'll walk through what the research says works best, the trade-offs involved, and why the "right" strategy depends on what you're really trying to optimize in retirement. 

Quote: "Smaller gifts sooner can be more impactful than larger gifts later." - Benjamin Brandt

We've also got a great listener question from ...

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February 9, 2026 18 mins

Is there an ideal level of wealth? Our Retirement Headline comes from Nick Maggiulli, who starts by rejecting the usual vague answers—"it depends," "on your own terms," or "whatever makes you happy." Instead, he tries to give a practical, math-based answer that works for most people, even if it's not perfect for everyone. 

Then our listener question is "How should we think about future income sources—like Social Security and pensio...

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February 2, 2026 21 mins

Andrew Rosen, CFP®, CEP, writes in a Kiplinger article how to walk through several common reasons people keep working — even as retirement comes into view.

Rather than looking at money first, the author looks at motivation and breaks it into five broad categories:

Category 1: I must keep working
Category 2: I probably should keep working
Category 3: I want to keep working
Category 4: I'm afraid to retire
Category 5: I don't know wh...

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Can you relate to this statement: "They've done everything right financially… but still can't bring themselves to spend the money they've saved."

In today's Retirement Headline, Meghaan Lurtz explains why underspending in retirement is usually rooted in psychology, not math.

Lurtz shares several common barriers:

  • Fear of future dependence
  • Doom forecasting
  • And an Identity tied to being a saver

Resource:

  • Article by Meg...
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"Just 10% plan to wait until age 70" to claim Social Security in retirement — and it's not because of a knowledge problem. 

We discuss this from a new survey that suggests most Americans may be claiming Social Security earlier than is financially optimal because fear is driving the decision. They understand the math—but they're still claiming early.

We also answer a listener 2-part question about where to park short-term cash in in...

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Paul Morrison details how Medicare premiums, including the IRMAA surcharge, are inflating at a rate higher than Social Security COLAs. This disparity is causing concern, as premiums can potentially consume a retiree's entire Social Security benefit over time, especially for those in higher IRMAA brackets for an extended period.

Paul provides concrete examples of how extended periods in higher IRMAA brackets could lead to Medicare p...

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A special recording from Andy Panko for his Retirement Planning Education Podcast: We discuss how the financial industry is evolving, the common struggles of "super savers" in retirement, and the importance of aligning financial decisions with life goals, not just spreadsheets. 

We talk about the role of Monte Carlo simulations, the importance of flexibility in financial plans, and the evolving role of advisors in a changing world.

...

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