You’ve done the hard work. You saved consistently, built a seven-figure portfolio, and are ready to enjoy retirement. But even millionaire retirees can make mistakes that put their plans at risk. In this episode, Devin shares the five most common retirement mistakes he sees among high-net-worth clients. These include missing long-term tax planning opportunities, underestimating healthcare and long-term care costs, failing to plan for success as well as failure, approaching income withdrawals wit...
Jul 21, 2025•31 min
In this episode, we break down the newly signed One Big Beautiful Bill Act (OBBBA) and what it means for retirees. From the extension of the 2017 tax cuts to new rules around Roth conversions, Social Security taxation, and a brand-new "Senior Deduction"—there’s a lot packed into this legislation. We’ll walk you through the major provisions, highlight how they may affect your retirement income strategy, and share practical planning moves to consider. Although this show does not provide specific t...
Jul 14, 2025•32 min
Today we answer a question from Ken, a recent retiree at 63, about how his Social Security claiming decision impacts his wife’s future spousal benefit. We break down how spousal benefits are calculated, whether the FRA (Full Retirement Age) amount is frozen when you claim early, and how COLA (Cost of Living Adjustments) factor into the equation. Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their individual firms. 📍Contact Dev...
Jul 03, 2025•3 min
Most retirees think tax planning ends with knowing their tax bracket, but that’s just the beginning. In this episode, we unpack how different income sources interact in retirement, and how seemingly smart decisions can trigger hidden taxes, Medicare surcharges, and other costly surprises. Learn how to avoid the traps and make your retirement income work smarter. Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their individual fir...
Jun 24, 2025•34 min
Today we answer a question from Chris about The Good Life Abroad and whether we plan to take a trip with the company. We share our thoughts on the concept, what interests us about their offerings, and whether a future review might be on the horizon. Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their individual firms. 📍Contact Devin’s team at https://carrolladvisory.co/podcast1 📍Contact John’s team at https://www.rossandshoal...
Jun 19, 2025•7 min
Today we answer a question from Sandi about how much umbrella insurance coverage you really need — especially as you approach retirement. We discuss why someone might choose a $2 million policy, how assets like home value, retirement accounts, and savings factor in, and share real-world examples to help you gauge whether you’re over- or underinsured. Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their individual firms. 📍Contac...
Jun 05, 2025•13 min
Today we answer a question from Peter about what happens when a parent dies with a fully planned estate that avoids probate — and how the Small Estate Affidavit process works in practice. We discuss handling unexpected estate assets like refund checks, whether you can open an estate bank account without letters testamentary, and who’s responsible for final taxes and bills Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their indi...
May 29, 2025•13 min
In this special episode, we catch up on a backlog of insightful listener questions—covering everything from estate planning and Social Security taxation to Roth conversions and Medicare rules. If you’ve been wrestling with real-world retirement planning decisions, you’re not alone. Today’s episode delivers practical answers to the kinds of issues many people face but few have clearly explained. We tackle: IRMAA and Social Security Taxation – Does IRMAA include Social Security income if it’s not ...
May 26, 2025•41 min
In the final installment of our 3-part estate planning series, we dive into one of the most overlooked—but critically important—aspects of planning: protecting your heirs’ inheritance. It’s not enough to simply leave assets to your loved ones. Without proper planning, those assets could be exposed to divorce, lawsuits, creditors, or mismanagement. We’ll explore how using trusts can provide long-term protection and flexibility, and why leaving assets outright may be a costly mistake. You’ll learn...
May 19, 2025•48 min
Today we answer Jeff’s question about using home equity to pay for end-of-life care — from tapping into equity for in-home support to selling the home to cover nursing home costs. In high-cost states like California, many seniors are house rich and cash poor, and this episode explores strategies to help families navigate that challenge. Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their individual firms. 📍Contact Devin’s team...
May 15, 2025•13 min
In this episode, we shine the light on common estate planning mistakes that can derail even the best intentions. We discuss the risks of failing to update beneficiary designations and why relying solely on joint ownership can create unexpected complications. Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their individual firms. 📍Contact Devin’s team at https://carrolladvisory.co/podcast1 📍Contact John’s team at https://www.ros...
May 12, 2025•29 min
Today we answer a question from Cathy about helping aging parents in California navigate care costs, preserve limited resources, and explore options like pro bono legal support. Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their individual firms. 📍Contact Devin’s team at https://carrolladvisory.co/podcast1 📍Contact John’s team at https://www.rossandshoalmire.com/ If you’re thinking, "I love the Big Picture Retirement podcast...
May 08, 2025•12 min
In this episode, we cover key tax considerations around wealth transfer. We cover the differences between federal estate tax and state inheritance tax, and explain why the stepped-up basis is such a powerful tool for minimizing capital gains taxes for heirs. Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their individual firms. 📍Contact Devin’s team at https://carrolladvisory.co/podcast1 📍Contact John’s team at https://www.ros...
May 05, 2025•39 min
In this episode, Brian asks some great questions about using Net Unrealized Appreciation (NUA) for company stock inside a 401(k). We dive into the rules, timing, and strategies that could lead to major tax savings— if you do it right . We cover: What exactly is NUA and why it matters Can you use NUA before retirement? Do you need to be age 59½? Can you move the stock out in segments, or does it have to be all at once? Common mistakes that could cost you Although this show does not provide specif...
May 01, 2025•9 min
In this episode, we explore how to pass on your assets smoothly and efficiently—without dragging your loved ones through probate court. You’ll learn why probate can be costly and time-consuming, and how non-probate strategies like beneficiary designations, joint ownership, and revocable living trusts can help you keep more money in your family’s hands and less in legal fees. Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their i...
Apr 28, 2025•27 min
In this inbox episode, we break down how the Social Security earnings limit works—especially for C corp owners who split income between salary and dividends. Learn what counts toward the limit, what doesn’t, and how smart income structuring can help you avoid benefit reductions. Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their individual firms. 📍Contact Devin’s team at https://carrolladvisory.co/podcast1 📍Contact John’s te...
Apr 24, 2025•7 min
In the first part of our series on estate planning, we laid the groundwork for why incapacity planning matters and what documents you need to get started. But there’s more to it than just having your paperwork in order. In this second episode on planning for incapacity, we take the conversation further by focusing on what happens when long-term care is needed. We’ll walk through the different types of care—home care, assisted living, and nursing homes—and how to plan ahead financially using priv...
Apr 21, 2025•46 min
Today kicks off a brand-new series on estate planning. Estate planning is one of those things everyone knows they should do—but far too many people put it off, sometimes until it’s too late. And the truth is, whether your financial situation is complex or pretty straightforward, having a solid estate plan isn’t just about what happens after you're gone. It’s also about making things easier for your loved ones—and protecting yourself—while you're still here. That’s why we’re launching this specia...
Apr 14, 2025•31 min
John asks about buying the individual sectors of the S&P 500 and rebalancing based on performance instead of simply buying an index fund. Devin shares the pros and cons that he can see with this strategy and shares what he thinks is a better approach. Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their individual firms. 📍Contact Devin’s team at https://carrolladvisory.co/podcast1 📍Contact John’s team at https://www.rossan...
Mar 20, 2025•8 min
Rosemary’s husband is scaling back to 32 hours a week as part of his transition plan before switching careers. With Social Security in mind, she asks: Will this reduced income impact their future benefits? In this episode, we break down how Social Security calculates benefits, whether lower earnings in the final working years can reduce your check, and what to consider before making the shift. If you’re thinking about adjusting your workload before retirement, this is an episode you won’t want t...
Mar 13, 2025•5 min
Planning to travel in retirement? In this episode, I sit down with Andrew Motiwalla from The Good Life Abroad to discuss how retirees can make the most of their travel experiences—without the stress. We talk about: ✅ Why travel is at the top of most retirees' bucket lists ✅ How to plan trips that align with your passions ✅ The best underrated destinations for immersive experiences ✅ How to avoid common travel planning pitfalls ✅ How long-term travel is changing the way retirees experience the wo...
Mar 10, 2025•36 min
This week, we’re diving into a question about the tax treatment of Special Needs Trusts. There are two types—First-Party and Third-Party trusts—but how does each one affect taxes? We’ll break down key differences in taxation, who reports the income, and what trustees need to consider when filing returns. If you or a loved one rely on a Special Needs Trust, understanding the tax implications is essential. Tune in for a clear and practical breakdown! Although this show does not provide specific ta...
Mar 06, 2025•10 min
For countless retirees, the greatest challenge isn't saving money, but spending it. After years of diligent saving, the transition to drawing down those hard-earned funds can be fraught with anxiety and uncertainty. But what if there was a way to ease this tension? In this episode, we explore the often unexpected emotional hurdles of retirement spending and reveal the antidote: a well-defined plan. With the right roadmap, retirees can grant themselves permission to spend, savoring the fruits of ...
Mar 03, 2025•36 min
Dan asks: If monthly income from an IRA exceeds $2,908 for a single person, would that result in disqualification for Medicaid? We break down the income limits, potential strategies to navigate Medicaid eligibility, and how certain tools—like Qualified Income Trusts (Miller Trusts)—can help individuals qualify despite exceeding the income cap. Tune in for a clear explanation of how Medicaid rules apply to retirement accounts and long-term care planning. Although this show does not provide specif...
Feb 27, 2025•10 min
We’ve heard this hundreds of time... 'I wish someone had warned me about this when I retired.' More often than not, they're referring to one of five key challenges that catch many retirees by surprise. In today's episode, we're diving into each of these five areas. If you're on the cusp of retirement, this is crucial viewing to help you steer clear of unexpected hurdles and enter this new phase of life with confidence. Pay particular attention to the last point–it's the most frequently mentioned...
Feb 24, 2025•34 min
In this episode, Tammy asks about the pros and cons of doing Roth conversions in retirement to manage Required Minimum Distributions (RMDs) down the road. With $2.9 million in combined IRAs and current income of $196,000, she’s concerned about future tax implications. While we can’t give personal advice, we’ll break down the potential benefits, drawbacks, and factors retirees like Tammy should consider when deciding if Roth conversions make sense. If you’re thinking, "I love the Big Picture Reti...
Feb 20, 2025•8 min
Cryptocurrency has changed the financial landscape, and that includes estate planning. Unlike traditional assets, crypto presents unique challenges—there’s no customer service line to recover lost passwords, and without proper planning, your digital assets could be lost forever. If you’re thinking, "I love the Big Picture Retirement podcast!” please consider rating and reviewing this show! This helps us support more people -- just like you -- move toward a confident retirement. Just scroll down ...
Feb 17, 2025•23 min
In this episode, we dive into Stephen’s fascinating question about estate planning for the far future—trusts designed to preserve wealth for individuals who undergo cryonic preservation. Is this cutting-edge legal strategy realistic, or is it more science fiction than practical planning? John can barely contain his excitement as we explore the legal, financial, and philosophical implications of planning for a revival hundreds of years down the line. If you’re thinking, "I love the Big Picture Re...
Feb 13, 2025•23 min
Your mindset can make or break your retirement. Are you a Pollyanna, Delegator, Controller, or Realist? In this episode, we dive into the four common mindsets retirees bring to the table and how each one impacts their financial, tax, and legal decisions. From blind optimism to overconfidence, we explore the strengths and pitfalls of each mindset—and how you can evolve to make better choices. Whether you're just starting to plan or reevaluating your approach, this episode will help you identify y...
Feb 10, 2025•43 min
In this episode, we tackle Richard’s question about why it might make sense to use IRA (non-Roth) accounts first to pay for long-term care expenses. We’ll explain the reasoning behind this strategy, including the tax implications, potential benefits for your overall financial plan, and how it fits into managing your retirement assets. If you’re thinking, "I love the Big Picture Retirement podcast!” please consider rating and reviewing this show! This helps us support more people -- just like you...
Feb 06, 2025•22 min
