Employee benefits are one of the most overlooked aspects of financial planning. We often check a few boxes during open enrollment and move on—but are we truly maximizing what's available to us?

This week, we sit down with Joe Saul-Sehy, host of Stacking Benjamins, to uncover the hidden value in workplace benefits. From disability insurance pitfalls to term vs. whole life insurance, Joe walks us through key strategies to ensure we're not leaving money (or protection) on the table.

Joe also introduces a powerful HR benefits guide, a resource designed to help us navigate workplace perks with confidence. Whether it's understanding own-occupation disability insurance, avoiding junk policies, or knowing when to self-insure, this conversation is packed with actionable advice. If you've ever wondered whether you're making the most of your benefits—or if you're just blindly accepting what's offered—this episode is for you.

• Benefits Guide: https://www.stackingbenjamins.com/benefits
• Website: Stacking Benjamins

Connect with Benjamin Brandt:

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Retirement Starts Today: Your Non-financial Guide to an Even Better Retirement

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Did you receive a windfall late in the year and then get penalized for not paying estimated taxes on it earlier? It doesn't seem fair, but the IRS might levy a penalty for that. There is a way to fix it - and similarly for RMDs you might take out in December too.

That's the main focus on today's Retirement Headline - and it fits in nicely with our Listener Question as well.

Resources:

• Article by Jeff Levine on the Nerd's Eye View Blog: Using Retirement Accounts To Reduce Estimated Tax Penalties Via Tax Withholding From (Required Minimum) Distributions
• IRS form 2210: Underpayment of Estimated Tax by Individuals, Estates, and Trusts

Connect with Benjamin Brandt:

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Retirement Starts Today: Your Non-financial Guide to an Even Better Retirement

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A Barron's piece from Jonathan Shenkman shares 6 reasons to think twice before you convert a Roth IRA. I agree with some of them - but strongly disagree with others because they apply to Super Savers - listeners of this show - differently.

We will go through all six with my additions for a Super Saver like you.

Then we answer a listener question from a 62 year old who is about to retire and wants to bridge the gap until he begins pulling in Social Security at age 70.

And you know we have a great Retire To Something segment to wrap up the show. Enjoy!

Resource:
Barron's article by Jonathan I. Shenkman: "6 Cases When a Roth IRA Conversion Isn't a Smart Move"

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

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Retirement Starts Today: Your Non-financial Guide to an Even Better Retirement

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Christine Benz got a text from a friend the other day. A mutual friend from college was retiring because he'd "hit his number in the stock market".

Most people would read that and think, good for him. Benz says all her alarm bells went off. Not out of envy. In her experience, "I hit my number" is usually a sign that the plan behind it isn't much of a plan.

Today we discuss two different ways Christine says people gets this wrong.

We also tackle a listener question asking if $1,000,000 is enough and wrap things up with a Retire To Something story.

Resource:
Article by Christine Benz in Morningstar: "Why I Object to 'Hitting a Number' for 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

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Retirement Starts Today: Your Non-financial Guide to an Even Better Retirement

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The term "Sandwich Generation" has been around since the 80s. You're the one in the middle - with aging parents on one side and dependent kids on the other.

Dan Haylett shared an article he calls The "Open Sandwich" Generation, which is after your parents pass away.

We will discuss Dan's article on what happens when the slices come off.

In our Listener Question segment, I'm asked "How do you do estate planning when you don't have anybody to name?"

And we wrap it up with a story that hits true to the meaning of "Retiring To Something".

Resource:

• Article by Dan Haylett: The 'Open Sandwich' Generation


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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The 2025 Milliman Long-Term Care Index put a number on long-term care: $135,000, the lump-sum amount an average 65-year-old would need to set aside today to cover the expected lifetime cost of long-term care.

But there are some details you need to know that make up that number. About half of those who need paid long-term care only do so for less than a year (averaging $30,000 in total cost). The other half need care for more than 5 years at an average of $665,000. $135,000 is just the average.

We will also take a question with multiple millions wanting to know if he should buy long-term care insurance or self-fund?

Resource:

• Article by Christopher Giese, Annie Gunnlaugsson, Evan Pollock, and Kevin Brown: 2025 Milliman Long-Term Care Index

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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A Corebridge Financial's decumulation study found 70% of American retirees say it's "very important" that their nest egg doesn't shrink in retirement. Another result found 38% say they've spent less than they wanted to- but not because the money isn't there. They spent less specifically to keep the balance from going down.

We go over more results from the study and what they mean in today's episode.

In our Listener Question segment, a married person has two pensions. While he's alive, the guaranteed income covers everything. If he dies first, his wife loses half of it. So how do you account for that WITHOUT drastically underspending your portfolio?

Finally, we wrap up the show with our Retire To Something segment.

Resources:

• Article by Vawn Himmelsbach in Moneywise: 'It's not the climb up. It's the way down': 38% of retirees have trouble spending their money
• Read And Feed program: https://readandfeed.org

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

A rule changed on January first that takes the tax deduction away from catch-up contributions for a lot of people who are still working. We'll run through all the 2026 numbers and talk about whether it's still worth doing.

In our Listener Question segment, a fellow in Connecticut is worried that the low-income window he's been counting on for Roth conversions may never show up, because his wife is a high earner four years younger than he is. He's come up with a clever workaround.

And to close out the show we hear from a retired HR Manager. After building a successful career, he found a meaningful way to give back through Reading Partners, serving as a remote reading tutor for students who need extra support.

Resources:

• Article by Amy Arnott in MorningStar: Should Higher Earners Still Make 401(k) Catch‑Up Contributions?
• Reading Partners: https://readingpartners.org

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