Retirement Starts Today

Latest Episodes:

The Hidden Cost Of Investment Income Mar 23, 2026

Show notes

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For our Listener Question: "Are brokerage account gains taxed before the money is withdrawn?" If you've ever wondered how your taxable investment account stacks up next to your IRA or Roth, this one's for you. We dig into the 'magic middle' of retirement savings and clear up how and when Uncle Sam wants his share.

And to wrap up the show, Dave in New York shares his work of raising dogs to help the blind. 🦮

Resource: Article by Larry Sweroe in Financial Advisor Magazine: The Hidden Cost Of Investment Income

Connect with Benjamin Brandt:

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Get the book!Retirement Starts Today: Your Non-financial Guide to an Even Better Retirement

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The Medicare Charge That's Taking a Bigger Bite Out of Social Security Checks Mar 16, 2026

Show notes

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." Tune in to hear that one!

And we wrap it up with our "Retire to Something" segment from Dave in Massachusetts.

Resource:

Wall Street Journal article by Laura Sanders: The Medicare Charge That's Taking a Bigger Bite Out of Social Security Checks

Connect with Benjamin Brandt:

Subscribe to the This Week in Retirement: http://thisweekinretirement.com
Get the Retire-Ready Toolkit: http://retirementstartstodayradio.com
Work with Benjamin: https://retirementstartstoday.com/start

Get the book!Retirement Starts Today: Your Non-financial Guide to an Even Better Retirement

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Tax Return Red Flags Mar 09, 2026

Show notes

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":

Very Low or Zero Taxable Income
Charitable Giving After Age 70½ Without Using QCDs
Donating Cash Instead of Appreciated Securities
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

Connect with Benjamin Brandt:

Subscribe to the This Week in Retirement: http://thisweekinretirement.com
Get the Retire-Ready Toolkit: http://retirementstartstodayradio.com
Work with Benjamin: https://retirementstartstoday.com/start

Get the book!Retirement Starts Today: Your Non-financial Guide to an Even Better Retirement

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Stop Chickening Out Mar 02, 2026

Show notes

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 contingencies and chasing 100% certainty in a world where it doesn't exist.

We go over Jordan's article "Stop Chickening Out" in our headline segment.

Then we answer Robert's question: "What if you just use the Traditional IRA for living expenses instead? If both approaches reduce the IRA balance and lower future RMDs, is Roth conversion strategy overhyped?"

And we wrap up the show with a story from one of our happiest retired listeners in our newest listener-sourced segment "Retire to Something".

Resources:

Article: "Stop Chickening Out" by Jordan Grumet Jordan Grumet interview on our show: https://retirementstartstodayradio.com/purpose-vs-purpose-an-interview-with-doc-g-ep-382

Connect with Benjamin Brandt:

Subscribe to the This Week in Retirement: http://thisweekinretirement.com
Get the Retire-Ready Toolkit: http://retirementstartstodayradio.com
Work with Benjamin: https://retirementstartstoday.com/start

Get the book!Retirement Starts Today: Your Non-financial Guide to an Even Better Retirement

Follow Retirement Starts Today in:Apple Podcasts, Spotify, Overcast, Pocket Casts, Amazon Music, or iHeart

8 Tips to Stop Worrying About Running Out of Money in Retirement Feb 23, 2026

Show notes

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: Reduce Future Tax Uncertainty Anchor 6: Maximize Guaranteed Income Anchor 7: Protect Against Long-Term Care Costs Anchor 8: View Home Equity as a Backstop

For our listener question: I've said before that accumulation is the easy part - and distribution is harder. But Kevin wrote in to say "wait a second… don't prices move around when you're buying or selling? So what's the real difference?" We're going to unpack why dollar-cost averaging on the way in is not the same thing as sequence risk on the way out — and why that distinction matters once you're living off the portfolio.

And to wrap up the show, we'll hear from Bernie about how he is blending service & fun for an even better retirement.

Resource:

Article by Sheryl Rowling in Morningstar: 8 Tips to Stop Worrying About Running Out of Money in Retirement

Connect with Benjamin Brandt:

Subscribe to the This Week in Retirement: http://thisweekinretirement.com
Get the Retire-Ready Toolkit: http://retirementstartstodayradio.com
Work with Benjamin: https://retirementstartstoday.com/start

Get the book!Retirement Starts Today: Your Non-financial Guide to an Even Better Retirement

Follow Retirement Starts Today in:Apple Podcasts, Spotify, Overcast, Pocket Casts, Amazon Music, or iHeart

The Best Way to Leave Money Behind Feb 16, 2026

Show notes

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 Tom about the three big company retirement plans — 401(k)s, 403(b)s, and 457s. On the surface they all look the same, but the rules under the hood are very different, and those differences can have a huge impact on taxes, flexibility, and when you can actually use your money. We'll break down what "qualified" really means, which accounts may be easier to tap earlier, and how to think about simplifying all of this as you head into retirement.

And we wrap up the episode with what our happiest retired listeners are up to in our "Retire to Something" segment.

Article:

The Best Retirement Strategies for Leaving Money Behind by Amy C. Arnott, CFA in Morningstar

Connect with Benjamin Brandt:

Subscribe to the This Week in Retirement: http://thisweekinretirement.com
Get the Retire-Ready Toolkit: http://retirementstartstodayradio.com
Work with Benjamin: https://retirementstartstoday.com/start

Get the book!Retirement Starts Today: Your Non-financial Guide to an Even Better Retirement

Follow Retirement Starts Today in:Apple Podcasts, Spotify, Overcast, Pocket Casts, Amazon Music, or iHeart

The Ideal Level of Wealth Feb 09, 2026

Show notes

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 pensions—in terms of our net worth? Should we include the present value of that income?"

Finally, in our "Retire to Something" segment, we're learning from an anonymous HR manager that is deploying their skillset in a totally new way in retirement.

Resource:

Article by Nick Maggiulli in Of Dollars & Data: The Ideal Level of Wealth

Connect with Benjamin Brandt:

Subscribe to the This Week in Retirement: http://thisweekinretirement.com
Get the Retire-Ready Toolkit: http://retirementstartstodayradio.com
Work with Benjamin: https://retirementstartstoday.com/start

Get the book!Retirement Starts Today: Your Non-financial Guide to an Even Better Retirement

Follow Retirement Starts Today in:Apple Podcasts, Spotify, Overcast, Pocket Casts, Amazon Music, or iHeart

Why are You Still Working? Feb 02, 2026

Show notes

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 why I'm still working

The author suggests borrowing from a concept by Artiste called "First Principles Thinking". Listen in for the answer.

Also, our listener Maria asks about the timing of your first RMD (Required Minimum Distribution): "If we want to skip our 1st RMD and take two the following year, how does that work?"

Resource: Article by Andrew Rosen, CFP® in Kiplinger's "Why Are You Still Working?"

Connect with Benjamin Brandt

Subscribe to the This Week in Retirement: http://thisweekinretirement.com
Get the Retire-Ready Toolkit: http://retirementstartstodayradio.com
Work with Benjamin: https://retirementstartstoday.com/start

Follow Retirement Starts Today in:Apple Podcasts, Spotify, Overcast, Pocket Casts, Amazon Music, or iHeart

Get the book!Retirement Starts Today: Your Non-financial Guide to an Even Better Retirement

Helping Underspenders And "Savers" Understand They CAN Spend More Jan 26, 2026

Show notes

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 Meghaan Lurtz: "Helping Underspenders And "Savers" Understand They CAN Spend More With 4 Stages Of "Experiments"

Listener question: "If I plan to retire at 65 1/2 or 66 and sign up for Medicare before 65 - but not for Parts B and D (because of my employer provided insurance) - will I have to pay a penalty to get Parts B and D (and Supplements) at a later date when I actually retire?"

Listen in to learn about creditable coverage and how penalties can stack up on themselves.

Connect with Benjamin Brandt

Subscribe to the This Week in Retirement: http://thisweekinretirement.com
Get the Retire-Ready Toolkit: http://retirementstartstodayradio.com
Work with Benjamin: https://retirementstartstoday.com/start

Follow Retirement Starts Today in:Apple Podcasts, Spotify, Overcast, Pocket Casts, Amazon Music, or iHeart

Get the book!Retirement Starts Today: Your Non-financial Guide to an Even Better Retirement

Americans May Be Claiming Social Security Too Early Jan 19, 2026

Show notes

"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 inflationary times and to actually buy Treasuries.

And we wrap up the segment to bring you our newest segment from you, the audience: "Retire to Something". If you'd like to share your story about what you are retiring "to", simply look for the link in the new "This Week in Retirement Newsletter" and fill out the super-quick form.

Connect with Benjamin Brandt

Subscribe to the This Week in Retirement: http://thisweekinretirement.com
Get the Retire-Ready Toolkit: http://retirementstartstodayradio.com
Work with Benjamin: https://retirementstartstoday.com/start

Follow Retirement Starts Today in:Apple Podcasts, Spotify, Overcast, Pocket Casts, Amazon Music, or iHeart

Get the book!Retirement Starts Today: Your Non-financial Guide to an Even Better Retirement

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