Chris’s Description
Jim and I talk about how market downturns—like the one we’re seeing now—can cause people to second-guess their plans, even when they’re well prepared. We walk through how our Secure Retirement Income Process is designed to provide structure and clarity during volatile times, and explain how proper positioning can help you maintain perspective.

Jim’s “Pithy” Description
Chris and I are back this week with a timely conversation—because if you’ve looked at the headlines lately, you’d think the sky is falling. “Boomers in Trouble,” “Retirement Fears,” you name it. Meanwhile, the S&P is down about eight and a half percent from its recent high, and you’d think it was 2008 all over again. I get it. Even folks with millions in savings start to feel uneasy when their statements show a dip. Especially if you’re newly retired and that paycheck just stopped coming.

So we took a step back and talked through why I built the Secure Retirement Income Process and the See Through Portfolio in the first place. It’s not about chasing returns—it’s about helping you see your money clearly. Which dollars are for next year? Which ones are for twenty years from now? That clarity matters. Especially when fear starts knocking.

And yes, I go on a bit of a rant (a productive one!) about how headlines prey on emotions, how panic can sabotage your go-go years, and how, if you’re not careful, you’ll rob yourself of the very fun you saved all those years to enjoy. I even share a new addition to my own bucket list—a historical tour through Italy, inspired by my latest deep dive into Roman history. You think I’m putting that off because the market’s down eight percent? Not a chance!

The post Weathering Market Downturns: EDU #2514 appeared first on The Retirement and IRA Show.

Jim and Chris discuss listener questions relating to spousal Social Security benefits, RMD tax withholding, IRA withdrawals, and 401(k) contribution limits. Jim also shares a PSA about a recent attempt at identity theft.

(20:15) Jim shares a PSA about a fraudulent payday loan application attempted in his name and what he learned about credit freezes and loan monitoring.

(30:15) George asks whether his wife will be subject to the earnings test if she retires mid-year and starts claiming Social Security benefits in the same year.

(39:15) George asks whether tax withheld from his RMD can satisfy IRS requirements for avoiding quarterly estimated taxes.

(47:30) A listener wonders whether taking cash from two small IRAs will result in capital gains taxes.

(1:03:00) Jim and Chris weigh in on a question about the total 401(k) contribution limit for those over age 50.

The post Identity Theft, Spousal Benefits, RMD Taxes, IRA Withdrawals, and 401(k) Contribution Limits: Q&A #2513 appeared first on The Retirement and IRA Show.

Chris’s Summary
Jim and I continue our review of interesting and sometimes confusing retirement planning facts, mostly drawn from Jim’s recent Ed Slott conference. We focus on the two Roth five-year rules and how they apply to Roth IRAs versus Roth 401(k)s. I explain the key distinctions between tax-free earnings and penalty-free access. Jim goes further into how “seasoning” from a Roth 401(k) carries over to a Roth IRA. We also touch on pro rata distribution rules in Roth 401(k)s, the IRS’s strict interpretation of the age 55 exemption, and the unique planning window between 59½ and RMD age.

Jim’s “Pithy” Summary
Chris and I continue our “things that make you go hmm” EDU series with more head-scratchers, funny moments, and some planning tips you’ll definitely want to remember. I came back from the recent Ed Slott conference with a pile of notes, and we dig into the most confusing—and most commonly misunderstood—rules surrounding Roth accounts: the dreaded five-year rules. I walk through both of them, explain how they apply to Roth IRAs and Roth 401(k)s, and we talk about the critical difference between tax-free and penalty-free withdrawals. Then we hit what I think is the big “ah-ha!” moment—the idea of “seasoning” Roth 401(k) dollars. Whether you picture that as a cast iron skillet like Chris or a cracked pepper roast like me, the point is: once a Roth 401(k) is fully seasoned, it keeps its flavor—even after being moved into a Roth IRA.

We also touch on a Roth 401(k) rule that surprises many people: how distributions are treated when they’re not qualified. Spoiler—it’s not like a Roth IRA! Plus, we go over a tax court case involving a guy who thought he was exempt from the 10% early withdrawal penalty and got hit with taxes, penalties, and interest anyway. It’s a cautionary tale, and the court’s response had us both shaking our heads.

Finally, we wrap up with some strategic talk about what Ed calls the “donut hole,” which matches what we refer to in the office as the tax planning window—that sweet spot between age 59½ and your RMD age when there are no penalties, no withdrawal restrictions, and total flexibility in how you tap your retirement accounts. If you’re doing any kind of serious tax or retirement planning, understanding this window is critical. Oh—and yes, there are plenty of food metaphors in this one, because I was hungry the whole show. Hope you enjoy!

The post Roth 5-Year Rules and the Tax Planning Window: EDU #2513 appeared first on The Retirement and IRA Show.

Jim and Chris discuss listener questions relating to Social Security strategies, spousal benefits, Roth conversions, and annuities.

(8:15) George asks whether a widow who was widowed before age 60 has two Social Security claiming strategies available based on the FRA benefit of each spouse.
(20:30) The guys address a question about how spousal benefits are calculated when one spouse took Social Security early and the other has a PERA pension.
(29:30) Georgette wonders how she and her husband should approach Roth conversions given their $4 million in IRAs, her larger balance, and concerns about future RMDs and legacy planning.
(1:03:30) Jim and Chris provide guidance on whether to use current or future spending when purchasing a SPIA to cover base expenses and how laddering might play a role.

The post Social Security Benefits, Roth Conversions, and Annuities: Q&A #2512 appeared first on The Retirement and IRA Show.

Chris’s Summary:
This week’s EDU show is a throwback to an old favorite—things that make you go “hmm.” Jim brought back a list of oddities from the latest Ed Slott training, covering everything from RMD rules the IRS only recently addressed to real-world court cases involving bankruptcy, lottery tickets, and IRA self-dealing gone wrong. Turns out, there are plenty of IRA mistakes you can make—some more ridiculous than others.

Jim’s “Pithy” Summary:
It’s another round of “things that make you go hmm,” straight from my latest trip to Ed Slott’s two-day training. These are the kinds of cases and quirks that catch my attention—some because they’re important, some because they’re just bizarre, and some because they make you wonder why no one’s brought them up before.

Ever wonder what happens if your IRA balance drops so low that you can’t take your full required minimum distribution? Turns out, the IRS finally put something in writing—but it took them long enough to address it.

Then there were some real-world case studies that left me shaking my head. One involved an all-or-nothing gamble with an IRA that didn’t go as planned. Another showed how trying to get too creative with IRA-owned real estate can backfire in a big way. And here’s one you probably haven’t thought about—doing an in-plan Roth conversion in your 401(k) might have unintended consequences that could close the door on a major tax strategy.

We’ll also talk about a handy tool for checking state estate and inheritance taxes—because where you live (or where you move) could have a bigger impact than you think.

Hope you enjoy the mix of useful, surprising, and “you’ve got to be kidding me” moments!

The post Things That Make You Go Hmm – RMD Rules, IRA Mistakes, and Tax Court Surprises: EDU #2512 appeared first on The Retirement and IRA Show.

Jim and Chris answer listener questions on Social Security records, GPO, QCD timing, annuity costs, and excess IRA contributions.

(10:30) Georgette asks about fixing gaps in her Social Security record.

(19:30) The guys discuss how a listener’s spousal Social Security benefits work after the repeal of GPO.

(28:30) George seeks clarification on the timing of QCDs and RMDs.

(53:30) Jim and Chris answer a query about the administrative costs of annuities.

(1:04:15) George faces challenges with excess IRA contributions and MAGI limits.

The post Social Security records, GPO, QCD Timing, Annuity Costs, and Excess IRA Contributions: Q&A #2511 appeared first on The Retirement and IRA Show.

Chris’s Summary:

Jim’s back from his conference and Jake joined the show again this week as we tackled the latest Ed Slott quiz. Unlike last time, Jim didn’t give us the book to reference—so Jake and I were going in cold. Jim also decided to test ChatGPT by giving it the entire quiz and the manual. With all that information, the AI was still imperfect.

While seeing if we could outscore both the AI and each other, we covered Inherited IRA RMD rules, SECURE Act 2.0, self-certification for disability, Roth 401(k) rules, and spousal consent for IRA beneficiaries.

Jim’s “Pithy” Summary:

It’s time for another Ed Slott IRA quiz, and this time, I decided to put both AI and my co-hosts to the test. Before the show, I handed the entire quiz—along with the Ed Slott manual—to ChatGPT to see if it could finally outscore us mere humans. Turns out, even with all that information, AI still flunked five questions. So, while the robots might be getting smarter, they’ve still got a long way to go before they can challenge a real retirement planner.

Chris and Jake joined me as we tackled some tricky questions on Inherited IRA RMDs, Roth 401(k) surprises, SECURE Act curveballs, and even some quirky beneficiary rules. To make things more interesting, I made sure they had no book, no notes—just their wits. And, of course, I had the pleasure of revealing exactly where the AI got it wrong (which, let’s be honest, was just as fun as answering the questions).

Along the way, we covered why certain Inherited IRA RMD rules have changed, how Roth 401(k)s can still trip people up, and why SECURE Act provisions aren’t always as straightforward as they seem. Plus, we had some fun debating the bizarre quirks of beneficiary designations—because apparently, even the IRS likes to keep us guessing.

Think you can outscore AI? Maybe even outscore Chris and Jake? Play along and see how you do!

The post IRA Rules Quiz: EDU #2511 appeared first on The Retirement and IRA Show.

Jim and Chris are joined by Paul Neiffer, CPA to answer listener questions on qualified dividends, gifting strategies, Roth conversions, and trust taxation.

(09:00) George wonders if frequent rebalancing in his taxable brokerage account is causing more of his dividends to be classified as unqualified.

(21:30) A listener asks for guidance on which accounts to withdraw from when planning a large financial gift to an adult son.

(37:15) The guys offer their perspective on doing Roth conversions early in retirement in order to reduce RMDs, and thus taxes, later in retirement.

(59:30) Georgette seeks clarity on revocable trust taxation, IRA beneficiary designations for minors, and whether a trust should be named as the beneficiary of a Roth or brokerage account.

The post Qualified Dividends, Gifting Strategies, Roth Conversions, and Trust Taxation: Q&A #2510 appeared first on The Retirement and IRA Show.

Chris’s Summary:
Jim is at yet another industry conference, so Jake is stepping in to join me this week. We pick up where Jim and I left off last time, discussing misleading financial articles. This time, we take a critical look at an article from Moneywise that claims to lay out the “standard” order for withdrawing retirement funds—but seems more focused on promoting paid links than providing useful advice. We break down why a one-size-fits-all withdrawal strategy doesn’t work, how tax planning should drive these decisions, and why you should always approach articles like this with skepticism.

Jim’s “Pithy” Summary (Even Though He’s Not in This One):
Well, I wasn’t on this episode because—surprise, surprise—I was off at an industry conference (again!), this time hunting for the next great fintech tool to help our office and clients. I’m always looking for ways to improve the advice we give, the services we offer, and maybe—just maybe—find a tool that doesn’t require me to beg Chris to teach me how to use it! Meanwhile, Chris and Jake tackled yet another clickbait financial article, this time from Moneywise, which attempted to pass off a barely disguised ad as solid financial advice.

Now, I haven’t listened to the episode yet, but I can already feel my blood pressure rising. Articles like this—pretending to provide helpful guidance while actually steering unsuspecting retirees toward whatever paid service they’re shilling that day—really get me going! From what I gather, Chris probably got straight to the point, and Jake—being the level-headed guy he is—kept things grounded with solid explanations. They covered why tax planning should drive your withdrawal strategy, how blindly following a set order can lead to higher taxes, and why taxable accounts might be more valuable later in retirement than these so-called experts admit. And I’m sure they took a few well-earned jabs at the deceptive ways financial content is being turned into a giant ad machine.

I’ll be back next week, but in the meantime, Chris and Jake are more than capable of keeping things straight—though, let’s be honest, the episode is probably missing at least one good rant from me, plus a few mispronounced words, incorrect names, and deep rabbit holes that make Chris sigh in exasperation!

The post Setting the Record Straight on Clickbait vs Reality: EDU #2510 appeared first on The Retirement and IRA Show.

Jim and Chris sit down to discuss listener questions relating to Social Security, 529 plans, Fun Vision, and Annuities.

(Intro – 12:00) Chris provides a Social Security PSA.

(19:00) A listener wonders whether her husbands Social Security benefits have been getting a COLA since his passing or if they’ve been frozen.

(26:00) A listener wonders if missed payment history from the 1980’s can be corrected and included when calculating their Social Security benefit.

(36:15) A listener asks about other alternative investment options for his 529 plans depending on the future of his daughters education needs.

(50:45) A listener wonders what the difference is between Fun Vision and the Fun Number.

(1:03:30) George looks for advice on taking his 401(k) as an annuity versus a SPIA down the line.

The post Social Security, 529 Plans, Fun Vision, and Annuities: Q&A #2509 appeared first on The Retirement and IRA Show.

Chris’s Concise Summary:
Jim and Chris examine a recent Suze Orman article on inherited IRA rules, identifying key errors that could mislead readers. They clarify the nuances of the 10-year rule, explain how the required beginning date determines whether annual RMDs are necessary and why Roth IRAs don’t have required minimum distributions. The guys also emphasize the importance of verifying financial information before making decisions.

A note to listeners: Regular listeners know that Jim is always looking for ways to improve. The podcast is no exception, so some changes are coming in the EDU episode descriptions! In this space, between the usual basic summary (now called Chris’s Summary) and the new, more detailed, Jim’s Summary, you’ll soon find links to related articles, documents, and other resources that Jim and Chris believe may be useful or interesting to listeners.

Jim’s “Pithy” Summary:
The guys take a critical look at a recent Suze Orman article discussing inherited IRA rule changes for 2025, identifying inaccuracies that could mislead readers navigating these complex rules. One key issue they highlight is the claim that all inherited IRAs, including Roth IRAs, require annual RMDs under the 10-year rule. Jim and Chris explain why this is incorrect and clarify that the rules depend on whether the original account owner had reached their required beginning date before passing away. They break down how the “at least as rapidly” (ALAR) rule applies to inherited accounts when RMDs were already in progress, ensuring listeners understand the distinctions that many articles fail to address.

The conversation also dives into Roth IRAs, reinforcing that they do not have required minimum distributions during the original owner’s lifetime, which means beneficiaries are not required to take annual distributions. Instead, most non-spouse Roth IRA beneficiaries can allow the funds to grow tax-free and withdraw the full balance in the 10th year. Chris and Jim stress that financial publications often oversimplify these rules, leading to confusion and potential missteps for individuals managing inherited accounts.

In addition to dissecting the article’s errors, the guys discuss broader issues with financial media, including the need for thorough fact-checking and the risks of relying on clickbait-style headlines for retirement planning guidance. They express concerns that many widely shared articles fail to provide the necessary nuance, which could result in readers making uninformed decisions.

Beyond the technical discussion, Jim and Chris also touch on upcoming podcast plans, including a potential follow-up episode covering a “Moneywise” article that Jim believes may be misleading in its own way. With Jim’s upcoming travel, they discuss the logistics of recording, including the possibility of Jake stepping in for an episode to analyze the “Moneywise” piece.

 

The post False Facts and Real Consequences: EDU #2509 appeared first on The Retirement and IRA Show.