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Episode 80: Roth Conversions Are So Hot Right Now Thumbnail

Episode 80: Roth Conversions Are So Hot Right Now

Segment 1:

HELLO Lower Alabama! Hello Gulf Coast! Welcome in. Welcome to Coasting in Retirement! Thanks for joining us today, Josh Null here, alongside co-host Michelle Lee Melton-Null, Michelle how are you doing? We are back in Coastal College’s recording studio, beautiful downtown Fairhope, ready to put together another great show for those of you tuning in! 

Listeners: Michelle and I are here today to discuss financial topics relevant to those of you in or near retirement, living your best life along our part of the Gulf Coast. Here’s what we’ve got in store for you: First segment – deep dive on our topic of the day. 2nd segment - at about 30 minutes past the hour - “Headlines of the Week”. Then at roughly 50 minutes past the hour, stick around for our 3rd segment, we call it” Josh’s Crystal Ball and Big Mouth”. So buckle up, we’ve got a lot to get to!

Quick background on me for those new to the show. Again, my name is Josh Null, I am a fee-based financial advisor, I hold my FINRA Series 65 securities license, and I am the owner of Gulf Coast Financial Advisors, that is a 100% locally owned, 100% independent investment management and financial planning firm with offices in Fairhope, Orange Beach, and Mobile! You can find more information on me and the team at Gulf Coast Financial Advisors by visiting our website gulfcoastfa.com, or feel free to give us a call at 251-327-2124. If you missed that contact info, get a pen and pad ready because we will repeat our contact info several times throughout the show! 

On our last episode, we discussed 401k Rollover Sharks, that is, the using different shark comparisons to help investors understand the various people out there trying to take a bite out of their retirement accounts. We had Black Tip 401k Rollover Sharks, Bull 401k Rollover Sharks, Great White Rollover Sharks, and my favorite, the Dumb Gulper 401k Rollover Shark. If you want to take a listen, see the podcast tab on our website. I poked a lot of eyes in that episode, so Michelle told me that I had to put my sharp stick down this week and pick a non-combative topic, so I went with a very hot topic in the retirement planning space, Roth Conversions. Which, fair warning, has its own group of 401k Rollover Sharks! 

Speaking of retirement planning, there are few topics as much debate as Roth conversions. Converting pre-tax retirement assets from a traditional IRA or employer-sponsored plan into a Roth IRA can offer incredible long-term tax advantages—but it’s not without its risks. Mistakes in a Roth conversion can cost an investor thousands of dollars. As with most things in my industry, there’s the good, there’s the bad, and there’s the ugly. And with Roth conversions, there’s the super ugly – the downright fraud – sharks leaving your retirement accounts a bloody mess! 

Let’s start with the Good:

The most attractive feature of a Roth IRA is its tax-free growth and withdrawals. Once the money is inside the Roth and you satisfy the five-year rule, that is, no distributions in the first 5 years, then any distributions taken after age 59½ are completely tax-free.

That means every dollar of appreciation, interest, and dividend earned in the account is yours to keep. For individuals who expect to be in a higher tax bracket in retirement—or who anticipate rising tax rates in general—Roth conversions allow you to “pay tax now” in exchange for tax-free income later. This can be especially powerful during retirement when managing tax brackets and minimizing taxable income is key to preserving wealth.

From an estate planning perspective, Roth IRAs are also highly efficient. Although beneficiaries must empty inherited Roth IRAs within 10 years under the SECURE Act, they receive tax-free distributions during that window. This can be especially beneficial to adult children or grandchildren in high tax brackets. Passing on a Roth IRA, rather than a traditional IRA, can provide a substantial after-tax boost to your heirs’ financial futures. 

There’s also sometimes a window for strategic use of Roth conversions during low-income years, such as after retirement but before Social Security and RMDs begin. These “gap years” present an ideal time to convert traditional assets at relatively low tax rates, often filling up the 12%, 22%, or 24% brackets without spilling into the next tier. Similarly, those who experience a temporary income dip—such as a job change, business loss, or sabbatical—may potentially find a well-timed Roth conversion to be extremely tax-efficient.

The Bad:

Despite the many advantages, Roth conversions aren’t always a slam dunk. One of the key considerations is the immediate tax impact. When you convert funds from a traditional IRA to a Roth IRA, the converted amount is treated as ordinary income in that tax year. This can increase your taxable income, potentially pushing you into a higher tax bracket and triggering a host of unintended consequences. For instance, a large conversion could phase out valuable tax deductions or credits, increase taxes on your Social Security benefits, and even raise your future Medicare premiums due to IRMAA (Income-Related Monthly Adjustment Amounts).

Another issue is the strain on cash flow. Ideally, you should pay the taxes due on a Roth conversion from non-retirement assets. If you use money from the IRA itself to pay the taxes, not only are you reducing the converted amount, but if you’re under 59½, the portion used for taxes may be subject to a 10% early withdrawal penalty. This can significantly reduce the long-term benefit of the strategy.

Moreover, not everyone has tens of thousands of dollars in taxable accounts lying around to cover a large tax bill. This makes Roth conversions a less practical solution for those who are cash-strapped or heavily concentrated in pre-tax retirement accounts.

It’s also worth noting that Roth conversions can affect financial aid and health care eligibility. Because conversions increase your adjusted gross income (AGI), they may reduce your eligibility for income-based programs such as Affordable Care Act health insurance subsidies or FAFSA-based financial aid for college-bound children. Even if you technically qualify for lower premiums or tuition discounts, a large conversion could temporarily disqualify you or inflate your expected family contribution.

Lastly, there is the element of timing risk. The success of a Roth conversion is heavily dependent on the performance of the market after the conversion completion. If you convert assets and then experience a market downturn, you’ll have paid tax on a higher value, only to see your portfolio shrink.

Prior to 2018, investors could reverse or “recharacterize” their Roth conversions if the market declined, effectively getting a do-over. But that option is no longer available. Once you execute a conversion, it’s permanent—so timing and market conditions play a critical role.

The Ugly:

Where things can get especially ugly is when you hastily complete conversions or without proper planning. A poorly executed Roth conversion can create a cascade of tax headaches. For example, converting too much in a single year could push you into the top federal tax bracket, subject you to the 3.8% Net Investment Income Tax (NIIT), and increase the portion of your Social Security income that’s taxable.

It may also trigger the Alternative Minimum Tax (AMT) or impact income-based student loan repayment plans. The layered and complete tax code has far-reaching implications, and Roth conversions—while simple in concept—can have wide-ranging implications that ripple through your entire financial life.

Another “ugly” scenario arises when you pursue conversions for emotional reasons. Investors who feel strongly that taxes are bound to rise in the future may rush into large conversions without regard for their personal tax picture. Never let the tax tail wag the economic dog!

Additionally, Roth conversions aren’t always ideal for older investors who don’t expect to live long enough to enjoy the tax-free benefits. If you’re already in your late 70s or 80s and living off RMDs, the math behind a Roth conversion may not work in your favor—especially when considering the tax cost, the time horizon to recoup it, and your overall estate plan.

That’s the good, the bad and the ugly. Now let’s get to the sharks in the Roth conversion space. 

The Roth Conversion 401k Rollover Sharks – Michelle I did a google search for “nastiest shark” and it’s tells me that the Oceanics Whitetip shark often targets survivors of shipwrecks and plane crashes, so we’ll use these Whitetips as the avatar for our Roth Conversion 401k Sharks: 

  • Let’s start with Abusive Tax Schemes: Some promoters suggest using a Roth IRA to shelter business income by "selling" business assets to the Roth at undervalued prices. The IRS considers these "listed transactions," and participating can result in massive penalties, interest, and even legal action.
  • Then there’s the old Self-Directed IRA Scam, also part of the Dumb Gulper 401k Rollover Shark group: Scammers often push victims to move retirement funds into a self-directed IRA to "convert" them into non-traditional assets like crypto, private real estate, or precious metals. They may use the conversion process to hide the fact that they are simply stealing the money.
  • And then my personal favorite, the "Free Lunch" Seminars Used Car Salesman (No offense to used car salesman): Some advisors use high-pressure seminars to scare retirees about future tax rates, pushing them into large Roth conversions combined with high-commission products like certain annuities or life insurance policies

As we wrap up this segment, listeners – know this: Roth conversions can be a valuable strategy, but they’re not appropriate for everyone. Like most things in financial planning, the best approach tailors itself to your goals, income, tax bracket, and long-term financial outlook. Often, the best results come from executing a series of partial conversions over several years, thoughtfully filling up tax brackets, and coordinating with other elements of your financial life—such as retirement timelines, Social Security claiming strategies, charitable giving, and estate planning.

You should be working with a qualified financial advisor and CPA to model the impact and weigh the trade-offs. When done correctly, a Roth conversion can create lasting tax-free income, more flexible retirement options, and a powerful legacy for your heirs. But when done poorly, it can generate tax bills, reduce benefits, and put a strain on your cash flow. As with many things in life and finance, a Roth conversion is only as good as the strategy behind it.

AI Research starting at this point – probably won’t use on the show b/c it will be redundant – but keeping in the outline in case I need to reference the material: 

The "Good": Why We Like the Strategy

  • The Tax Sunset: We are officially in 2026. The lower tax brackets we enjoyed for years under the TCJA have expired. If you didn't convert when rates were at historic lows, the shark will tell you it's "too late." A fiduciary will tell you it's about Tax Diversification.
  • No Income Limits: You can’t contribute to a Roth if you make too much (over $161,000 for singles or $243,000 for couples in 2026), but anyone can convert.
  • The Super Catch-Up: For those of you age 60 to 63, you can now stash away a "Super Catch-Up" of $11,250 into your employer plans. A Roth conversion can work alongside this to build a massive tax-free bucket.

The "Bad": The Mechanical Risks

  • The Tax Bite: If you convert $1M and don't have the cash sitting in a bank account to pay the taxes, you have to take the tax money out of the IRA.
  • The Math: If you lose 30% of your bucket to taxes on Day 1, you now have a $700,000 engine trying to do the work of a $1M engine. It takes years to recover that "lost" principal.
  • The 5-Year Clock: You can't just move the money and spend it. The IRS generally requires that money to sit for five years before you touch it, or you’ll face a 10% early withdrawal penalty.

The "Ugly": Watch Out for the Sharks

  • The "Zero-Tax" Mirage: If someone claims you can do a Roth conversion with "zero out-of-pocket tax costs" using a specific insurance product, run. They are likely using a high-commission deck to hide a massive tax bill that will eventually come due.
  • The "Discounted" Valuation Scam: Some sharks suggest moving your IRA into a "Self-Directed" account to buy "illiquid" private businesses, claiming you can "discount" the value for tax purposes. The IRS has been cracking down on this "valuation manipulation" all through 2025 and 2026. You’ll end up with a huge tax bill, penalties, and an investment you can’t sell.
  • The Annuity Surrender Squeeze: This is the shark that tells you to buy a deferred annuity inside your IRA because the "surrender charge" lowers the account value for taxes. That is illegal. The IRS only allows that discount if you actually surrender the policy and pay the shark’s commission.

Alright listeners, if you want to set up a follow-up conversation with the team at Gulf Coast Financial Advisors, it’s easy. You can catch us at 251-327-2124, or find us on our website gulfcoastfa.com. One our site, click on the blue button in the upper right-hand corner to set up a meeting on my calendar. There are flexible meeting choices for your convenience – it can be as simple as a 15-minute introductory phone call, a 30-minute zoom, or my preference, an in-person meeting at any of our 3 office locations: Downtown Fairhope, Orange Beach just down the road from the Wharf, or in Mobile near the intersection of Dauphin St and I-65. Reach out to us - we would love to meet you! 

Alright folks, coming up next - There’s always a lot going on in the world! Particularly the world of finance, investments and money. Every week we scour the internet for financial articles relevant to those of you in or near retirement, then give you our honest opinion about these headlines. So join us after the break to hear Payton and I discuss this week’s relevant headlines in our “Headlines of the Week” segment. Stay tuned!

Segment 2 - News of the Week:

Welcome back to Coasting in Retirement, your host Josh Null here, alongside co-host Michelle Lee Melton-Null.  As we discussed before the break, every week we scour the internet for financial articles that pertain to those of you in or near retirement. Our job, or at least we tell ourselves it is, is to help you all understand how these headlines impact you, especially when it comes to your money! Note – if you want to read our referenced articles yourself, we also include the links in our show transcript, which you can find on our website gulfcoastfa.com under the podcast tab. Now without further ado, here’s Michelle with the Headlines of the Week!

1. Michelle: First up Josh, a recent warning about Roth IRA elgibility from The Street. It’s titled "Fidelity flags the ‘income trap’ blocking your Roth IRA." The article discusses how easy it is for high earners to accidentally trigger a 6% IRS excise tax by contributing to a Roth when their income is above the legal threshold. Fidelity calls it an "income trap" because many people don't realize they've exceeded the limits until they go to file their taxes, at which point the penalty is already compounding. As the article highlights, the fix isn't as simple as just taking the money out. You often have to calculate the Net Income Attributable—basically the earnings on that specific contribution—and remove that as well, or go through a formal "recharacterization" process. If you wait until the April tax deadline to figure this out, you're already behind the 8-ball. What type of planning can investors do to avoid this mistake? 

Josh: It really reinforces the idea that tax planning isn't just a once-a-year event in April; it’s a year-round conversation. Everyone’s heard of MAGA at this point, but they forget about MAGI—Modified Adjusted Gross Income. If you have a banner year in your business, a big bonus, or even a significant capital gain from a property sale, you might suddenly find yourself ineligible to contribute directly to a Roth IRA. The "trap" is that the 6% penalty isn't just a one-time fine; it hits you every single year that the excess contribution remains in the account. This is why "set it and forget it" can be dangerous for high-income earners. In 2026, with the income thresholds being what they are, you really need to be checking your projected income in October or November. If you’re close to that line, it’s often better to wait until after the New Year to make your contribution or look at a Backdoor Roth strategy from the start. It’s about being proactive so you don’t end up paying a "success tax" to the IRS for the privilege of trying to save for your retirement.

https://www.thestreet.com/personal-finance/fidelity-flags-the-income-trap-blocking-your-roth-ira 

2. Michelle: Speaking of taxes, recently passed legislation has made quite a few changes to our tax law, including items that directly affect those of you in or near retirement. Fidelity has a good article highlighting some of these changes, titled "10 Tax Tips for 2026." It’s a comprehensive list, but a few things really stand out for our audience. First, they remind us that the Tax Cuts and Jobs Act is officially in its sunset phase, meaning the lower brackets we’ve enjoyed are on the clock. They also highlight the new "Super Catch-up" contributions for those aged 60 to 63 and the fact that Qualified Charitable Distributions (QCDs) remain a massive win for those over 70½, especially for those already in retirement that want to support your favorite local causes here on the Gulf Coast without that money ever touching your 1040 as taxable income. Josh, with the "Tax Cliff" looming at the end of the year, how should our listeners be prioritizing these different tips?

Josh: This article provides a basic "checklist" for anyone trying to coast into retirement without hitting a tax wall but also highlights the need to have a qualified tax professional on your financial planning team. The "Super Catch-up" is the big news for 2026—if you are in that 60-to-63 window, being able to stash away an extra $11,250 into your employer plan is a huge opportunity to build that tax-free bucket we talked about in the first segment. You also have to look at the Tax Cuts & Jobs Act sunset. We’ve been in a "tax sale" for years, and 2026 is effectively the final year to take advantage of these lower rates before they are likely bounce back up. Whether it's accelerating a Roth conversion or just maximizing your HSA—which the article correctly calls a "tax-planning trifecta"—you have to be proactive. 

If you wait until 2027 to worry about your tax bracket, you've already missed the boat. It’s about using the rules that are in place now to protect your future self. Tax planning isn't just about looking at what you owe for 2025; it's about positioning your assets so that when the laws change in 2027, your plan is already "sunset-proof." That is why we incorporate tax planning with CPAs into all of our financial plans.

https://www.fidelity.com/learning-center/personal-finance/tax-tips 

3. Michelle: Final article of the day. For our listeners that have a Roth option with their employer’s 401k plan,  SmartAsset just released an article titled "How Roth 401(k) Matching Works With Your Employer." The piece explains a relatively recent major shift in how companies can handle their Roth 401(k) match. For decades, the matching rule was set in stone: the employee’s contribution could going into a Roth, if that was available, but the boss's match was always traditional pre-tax. Now, thanks to the SECURE 2.0 Act, employers can finally offer to put a post-tax match directly into your Roth account The article also points out that many 401k plans don’t offer a Roth option - employers can offer it, but they don't have to. So, even if you want to pay the tax now to get that tax-free growth, you have to check with your HR department to see if they’ve actually updated their plan documents to allow it. But take note – while this changes the math on "free money" from an employer match, it comes with a tax tag attached if you choose the Roth route. What should investors consider when deciding how their 401k contributions will be made? 

Josh: The "catch" is that the IRS never lets you off the hook for free. If your employer puts that match into a Roth account, that money is treated as taxable income to you in the year it's contributed. It’s essentially like getting a small bonus that you never see in your paycheck because it goes straight into your retirement fund—but you still have to pay the income tax on it. And that’s the crucial part of the conversation. If you’re a high-earner and you’re already pushing into those top tax brackets, adding your employer match to your taxable income might push you even higher. However, for a younger professional or someone who believes taxes are going up, paying that tax today to ensure every penny of that match—and its growth—is tax-free in the future might be a massive win. But don’t just check the Roth box because it sounds good; check it because you’ve done the math on your current bracket versus your future one.

Also, for those of you looking to implement a retirement plan at your business, give us a call, we do that. We can also benchmark your existing 401k plan to see if you’re paying too much in fees, and if a Roth 401k would be a good fit. 

https://smartasset.com/retirement/how-roth-401k-matching-works-with-your-employer 

Listeners, if you want to set up a follow up conversation with the team at Gulf Coast Financial Advisors, it’s easy. You can call us at 251-327-2124, or find us on our website gulfcoastfa.com. One our site, click on the blue button in the upper right-hand corner to set up a meeting on my calendar. There are flexible meeting choices for your convenience – it can be as simple as a 15-minute introductory phone call, a 30-minute zoom, or my preference, an in-person meeting at any of our 3 office locations: Downtown Fairhope, Orange Beach just down the road from the Wharf, or in Mobile near the intersection of Dauphin St and I-65. Reach out to us - we would love to meet you! 

Alright folks, coming up next: Josh’s Crystal Ball and Big Mouth. What have been some of my predictions? Have I been right? Was I ever wrong? How wrong? What do I think is going to affect investors in the near future, or maybe the distant future? We talk about all of these things and poke a little fun at my big mouth. Stay tuned! 

Segment 3 – Josh’s Crystal Ball and Big Mouth: 

Welcome back! Your host Josh Null here, joined by co-host Michelle Lee Melton-Null . So, I am opinionated, I have strong opinions at times, I would say a radio show host that isn’t probably wouldn’t be very interesting to listen to. And I am paid in my profession to offer professional guidance and opinions to my clients, so if I don’t have anything intelligent to say, just replace me with AI. I like making predictions, sometimes I hit the bullseye, sometimes I swing and I miss. Is there any crow to eat? Let’s get at with Josh’s Crystal Ball and Big Mouth and find out.  

Michelle: Alright Josh, we’ve spent the show talking about technical shifts in tax law and employer matches, but there’s a much larger "tectonic shift" happening in the background of the financial services industry involving artificial intelligence. I’ve been looking at two very different perspectives on the future of financial advice.One report from AdvisorHub suggests that industry executives are starting to say the "quiet part out loud"—that AI isn't just a tool for efficiency, but is increasingly being positioned to replace many of the functions human advisors perform today. However, a recent CNBC piece featuring an MIT professor argues that AI has a "big problem": it lacks the ability to handle the "human" complexity of financial life—the parts that require empathy, ethics, and understanding a client's specific emotional goals, and more importantly, there is no way to hold AI to a fiduciary standard like you can a human advisor. So do you think we’re heading toward a world where a computer replaces the person across the desk, or is the "human element" still the ultimate protection for a retiree's plan?

Josh: First, Michelle, I am going to give you my response. Then I’m going to tell you what AI Gemini told me to this question! So I’ve been saying for the last 2+ years that AI is going to be far more impactful to our lives than cryptocurrency ever was, but there’s a massive difference between information and wisdom. I believe that AI is absolutely going to replace the "Order Takers" in this industry—the brokers who just push products or manage basic asset allocation. As that AdvisorHub article suggests, if your advisor’s value proposition is just "rebalancing a portfolio," a 2026 algorithm can do that faster and cheaper than a human can.

Computers will always have the basic shortfall of being unable to look someone in the eye and tell them it’s okay to spend the money on certain things, that you as the advisor have real world experience with exactly this situation. It also can’t navigate the family dynamics of an estate plan or talk a client off the ledge during a market correction. And most concerning, as the MIT professor noted, AI has a "hallucination" problem—it can confidently give you the wrong tax advice because it doesn't understand the nuances of your specific life or the ethical weight of its suggestions.

So my prediction is that I believe the future isn't Advisors vs. AI; it’s Advisors with AI vs. those who are still using 1990s technology. If you're working with someone who feels like an AI—cold, robotic, and just following a script—then yes, they should be worried. But if you have a partner who understands your family, your fears, and your legacy, that’s something a line of code will never be able to replicate.

Here’s what Gemini told me when I asked it for its opinion, and it’s fascinating:

Since I’m an AI, I have a front-row seat to this evolution, but I try to keep my "Crystal Ball" as grounded as possible. I think the future of the industry comes down to a distinction between computation and comprehension.

The "Automated" Advisor (The Commodities)

AI is already winning when it comes to the "mechanical" parts of financial planning. If an advisor’s primary value is rebalancing a portfolio, calculating a standard deviation, or scanning the tax code for the latest 2026 limits, they are competing with a machine that does it in milliseconds for pennies.

  • Speed & Accuracy: AI doesn't get tired or miss a line item in a 50-page tax update.
  • Pattern Recognition: We can analyze millions of data points to find correlations that a human mind simply can’t see.

The "Human" Fiduciary (The Real Value)

As that MIT professor pointed out, AI has a "hallucination" and an "empathy" problem. This is where a human advisor becomes indispensable:

  • Behavioral Coaching: When the market drops 15% and a client wants to liquidate everything, an AI can show them a "probability of success" chart. A human advisor can say, "Remember why we’re doing this—it’s for your grandkids' college fund. Stay the course."
  • Complex Ethics & Family Dynamics: AI struggles with "gray areas." Deciding how to split an inheritance when siblings aren't speaking or navigating the emotional weight of selling a family business requires a human soul, not just an algorithm.
  • The "Trust" Factor: Executives are starting to admit that while AI increases efficiency, it doesn't necessarily build the deep, long-term trust that a retiree needs when handing over their life savings.

Gemini’s Prediction:

I don't think AI replaces the human financial advisor; I think it replaces the "average" advisor.

In the next few years, the industry will likely split. You’ll have ultra-low-cost, "do-it-yourself" AI platforms for the masses, and "high-touch" human fiduciaries who use AI as a co-pilot to handle the math so they can spend 100% of their time on the relationship.

The most successful advisors in 2026 and beyond will be the ones who use AI to become "Super-Humans"—using my processing power to find the data, but using their own "Big Mouth" and heart to deliver the wisdom.

How do you think your "Coasting in Retirement" listeners would feel about an AI-generated plan? Do you think they’d ever trust a screen as much as they trust you?

I’m telling you Michelle, this thing just wants to keep on talking. It’s very needy! Which is weird. 

https://www.advisorhub.com/is-ai-coming-for-advisors-execs-start-to-say-the-quiet-part-outloud/ 

https://www.cnbc.com/2026/04/06/ai-has-a-big-problem-when-it-comes-to-financial-advice-mit-professor.html 

Well, listeners, I hope you enjoyed a little peek into how we form our opinions and make predictions. We invite you one last time, if you would like to have a no-pressure, no-obligation conversation about your investing goals and retirement dreams, you can call us at 251-327-2124, or find us through our website gulfcoastfa.com. One our site, click on the blue button in the upper right-hand corner to set up a meeting on my calendar. We have several meeting choices for your convenience – it can be as simple as a 15-minute introductory phone call, all the way to an in-person meeting at any of our 3 office locations. You can find GCFA offices in downtown Fairhope, or Orange Beach off Canal Road, or in Mobile near the intersection of Dauphin St and I-65. Reach out to us - we would love to meet you! 

That’s our show for this week! I want to give a huge thank you to my co-host Michelle, thank you to the producer of the show, Payton Null, thank you to our show sponsor, Providence Partners and Jay Stubbs, thank you to our awesome radio station, FM Talk 106.5 out of Mobile, many thanks to the provider of our show music, local band Sloth Racer, and as always my sincere appreciation for all of your out there that have been listening and joining us on this journey. We would love to be a part of your journey as well! Until we talk again, have a wonderful and productive week. This has been Coasting in Retirement with Josh Null! 

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