What happens when you reach financial independence by paying off a low interest rate mortgage early? Or being renter instead of buying a home and growing equity? I'll explain why hitting that milestone earns you the right to ignore some of the most stubborn rules in personal finance.
For our Listener Question: A listener wants to know how to think about real estate as part of a retirement portfolio — should they own a rental property for income?
And we will wrap it up with another listener-sourced segment called "Retire to Something".
Resource:
Article from Business Insider: "There’s No One-Size-Fits-All Path to Early Retirement"
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According to Capital One Shopping - 89% of shoppers have made some kind of impulse buy. More than half have spent more than $100 on a whim, and the average shopper made impulse buys adding up to $282 a month.
A classic rule is to wait 24 hours to help curb impulse buys, but on today's show, I'm going to flip that rule on its head and explain why my listeners might actually need the opposite advice.
After that, I'll answer a listener question about switching from saving for decades to a spending mindset? You'll learn about my "half for me, half for you" framework.
And to wrap up the show, I'll share what our happiest retired listeners are up to in our newest listener-sourced segment "Retire to Something".
Resource:
Article by Marc Buerti at Money.com: The "24-Hour Rule" That Keeps Retirees From Blowing Their Savings on Impulse Buys
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Imagine having 10 overstuffed boxes of grandma's collections in your living room.
That's the story that leads our show from a couple in Florida who received these items as hand-me-downs from a boomer parent trying to clear them out.
The article features estate specialist Julie Hall, who says Millennials don't want painted china or antique furniture — they want Pottery Barn and IKEA. When Hall asked her own daughter what she'd want from her house, the answer was, "Just the jewelry". Hall's takeaway? That response gave her permission to let go.
We discuss this growing issue in our headline segment before answering a listener's question: "Do you have any advice on giving money to adult children while still living? Giving them some of their inheritance while they are younger and need money more than later in their life when my husband and I pass away."
Then we wrap it up with a retired pastor who spends his time diving into a reef tank full of sharks at the Toledo Zoo in our "Retire To Something" segment.
Resource:
Article by Richard Eisenberg: Sorry, Your Kids Don't Want Your Stuff or Your Parents' Stuff
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There is roughly a ten-year window centered around your retirement date, five to ten years before, and five to ten years after called "The Retirement Risk Zone". This is when you're most vulnerable to sequence-of-returns impacting the longevity of your withdrawal strategy.
We cover this idea brought up by Wade Pfau in an episode of "The Long View", a show hosted by Christine Benz, Amy C. Arnott, and Ben Johnson - specifically:
After that, I answer a listener question: Frank is planning to delay Social Security and wants to know — does it make sense to take bigger withdrawals from the portfolio in your 60s and then scale back in your 70s once Social Security kicks in? Short answer: yes — but how you do it matters a lot. We'll walk through it.
Finally, in our "Retire to Something" segment: After 50 years in the workforce, a former Senior of VP in Manufacturing inspires us with ideas he is doing in his retirement.
Resources:
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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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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 "
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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?
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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.
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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:
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
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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
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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":
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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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
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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: 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
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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
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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
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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?"
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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:
Resource:
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.
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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 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.
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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 premiums exceeding Social Security benefits, forcing retirees to pay out-of-pocket.
Resources:
Contact Paul Morrison: paul@irmaacertifiedplanner.com
Website: irmaacertifiedplanner.com
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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.
It’s a conversation that encourages you to find joy and flexibility in your retirement journey.
Resources:
Andy's podcast: Retirement Planning Education
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Nick Maggiulli’s latest article in Of Dollars & Data challenges one of the core ideas that drives personal finance blogs, podcasts, and even some of our own thinking — the belief that financial independence should be the ultimate goal.
We explore the surprising downsides of chasing early retirement, the difference between financial independence and financial freedom, and why something called “Coast FIRE” might be the real goal worth aiming for.
I also answer a listener question: What can retirees do to fight back against inflation? One listener asks how to protect their buying power as costs keep rising. We go over several practical, actionable ways to stretch your dollars and build an inflation-resistant retirement.
Resource:
Article by Nick Maggiulli in Of Dollars & Data: Why Financial Independence is Overrated
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New research from David Blanchett, head of retirement research at PGIM, challenges one of the biggest assumptions in retirement planning: that happiness in retirement depends on maintaining a constant—or even increasing—level of spending.
⬇️ Upon entering retirement, households experience a median consumption decline of about 20%.
This drop is often viewed as a red flag in traditional financial planning models.
However, Blanchett argues that this decline is not necessarily problematic, especially when you look at how financial well-being changes over time.
☎️ Then on our listener question, we hear from a 34-year-old investor who’s been all-in on stocks since taking Dave Ramsey’s advice early in their career. Now, they’re wondering how and when to start easing into a more balanced portfolio with bonds.
We’ll talk strategy, psychology, and sprinkle in some data on market highs that might surprise you.
Resource:
Article by John Manganaro from ThinkAdvisor: Spending Drops in Retirement, but Satisfaction Doesn't: Blanchett
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Only 3% of Americans have saved $1 million for retirement. according to 24/7 Wall St. & AOL. I’ll break down what that means—and why your personal number might be more important than any national average.
After that, I answer a listener question where we tackle how to cover healthcare costs in early retirement—specifically for a 58-year-old retiree with a non-working spouse and three adult kids under 26 still on the family plan. We’ll explore ACA strategies, income planning, and a clever way to help the kids get their own coverage at a big discount.
Resource:
AOL article by David Beren: A Look at U.S. Workers Who’ve Accumulated $1M in Retirement Funds
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Most people focus on saving for retirement, but what happens when you actually get there? Retirement isn’t just about having enough money—it’s about managing risks that can threaten your financial security and lifestyle.
In this episode, we explore Five Key Retirement Challenges (and Solutions), inspired by a Kiplinger’s Personal Finance article by Walt West. From unexpected market downturns to rising healthcare costs, these challenges can catch retirees off guard if they’re not prepared.
We break down each challenge—financial instability, healthcare expenses, taxes, inflation, and estate planning oversights—and discuss practical strategies to navigate them. Learn how to structure a flexible withdrawal plan, prepare for long-term care costs, use tax-efficient strategies like Roth conversions, and ensure your estate plan protects your loved ones.
Plus, we tackle a listener question about using a MIGA ladder strategy to bridge the gap until Social Security—offering insights into the pros and cons of annuities in a retirement portfolio.
If you want to retire with confidence and avoid costly missteps, this episode is a must-listen. Whether you're years away from retirement or already in it, understanding these key challenges and their solutions can help you make smarter financial decisions for the road ahead.
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Many retirees enter their golden years with the goal of financial security, but what if the biggest risk isn’t running out of money—it’s not spending enough of it? A surprising new study reveals that retirees are withdrawing just 2% a year from their savings—barely half of what’s traditionally considered safe.
This cautious approach might seem responsible, but it often leads to unnecessary frugality, missed experiences, and larger-than-expected tax burdens later in life. The hesitation to tap into personal savings, even when there's plenty available, raises an important question: What’s stopping retirees from spending with confidence?
Research shows that retirees feel much more comfortable spending guaranteed income from sources like Social Security and pensions while being reluctant to withdraw from their own investments. This behavioral tendency can leave money unspent for decades, only to be forced out later through required minimum distributions (RMDs) that create tax inefficiencies. Meanwhile, large inheritances often arrive too late to make a meaningful impact on the next generation.
Rethinking the 2% mindset means understanding what keeps retirees locked into ultra-conservative spending habits and finding ways to turn savings into income that feels reliable. A simple shift—such as automating monthly withdrawals or adjusting expectations around financial security—can open the door to a more fulfilling retirement. The money was saved to be spent, and spending it well can be just as important as saving it wisely.
Spending too little can be just as costly as spending too much. With the right approach, retirees can enjoy their wealth now while keeping future financial security intact.
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