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 you are wondering: "How am I supposed to figure out what I want to do in retirement when I can barely find time to do laundry while I'm still working?" Great question!

And in our "Retire To Something" segment, Lois from the Southeast turned a lifelong love of animals into a retirement packed with purpose — volunteering at a zoo, working part-time at an aquarium, and spending half the year with manatees!

Resource:

Article by Janet Bodnar in Kiplinger: Stop Sweating the Small Stuff When You Spend Your Retirement Money


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

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Your beneficiary designations are probably outdated.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's "Retire to Something" listener talks about her definition of retirement, which might be the simplest and best one yet.

Resource:

Article by Daniel P. Michaelse on WealthManagement.com: "Five Beneficiary Designations to Review Now
"

Connect with Benjamin Brandt:

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

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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 guaranteed payouts and wondering: are these actually better than bonds for generating retirement income?

Then we wrap it up with our Retire "To" Something Segment: A listener who is only 2-5 years away from retiring wrote in with their very simple philosophy: "Never run away from a job. Instead, seek out the next better opportunity."

Resource:

Article by Ben Carlson: How Do Higher Oil Prices Impact Stock Market Returns?

Connect with Benjamin Brandt:

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

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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 retirement plan?"

Then stick around to hear what our happiest retired listeners are up to in our newest listener-sourced segment "Retire to Something"

Resource:
Article by Laura Saunders in the Wall Street Journal: Estimated Taxes Are a Pain. Here's How to Avoid Costly Penalties.

Connect with Benjamin Brandt:

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

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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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• 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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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:

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

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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

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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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