Big Picture Retirement®

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 doe...

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...

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 type...

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 you...

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.  📍Conta...

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...

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 avo...

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 ess...

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...

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...

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...

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 con...

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 he...

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 pl...

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. Wheth...

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...

From President Trump's upcoming tariffs on Canada, Mexico, and China to the historical legacy of the "Chicken Tax," tariffs have shaped economies and industries in ways both expected and unforeseen. In this episode, we dive into the purpose, pros, and cons of tariffs, exploring their impact on consumers, businesses, and global trade. Learn how these taxes can stimulate domestic production, drive u...

In this episode, we address Joe's question about how claiming Social Security benefits early can reduce withdrawals from retirement accounts and potentially lead to greater long-term growth. Joe shares his calculation comparing the cumulative Social Security benefit difference with the investment growth of withdrawals saved by filing early. Is he onto something, or is there a missing piece? Tune i...

A recent Supreme Court decision in Connelly v. United States has sent shockwaves through closely held businesses employing life-insurance-funded redemption-type buy-sell agreements. In this episode, we break down the case, the tax implications, and why the IRS may not respect your agreed-upon valuation. Discover why it's critical to review and, if necessary, restructure your buy-sell agreements to...

In this episode, we answer Lori's question about whether the repeal of the Government Pension Offset (GPO) will increase her survivor benefits and how it could impact benefits for those with similar circumstances. We also address Jesus's concern about whether his Social Security check will be reduced when he retires from TRS (Teacher Retirement System). If you've ever wondered how these rules migh...

Sometimes life throws curveballs, and you may end up retiring earlier than planned. In this episode, we dive into JP Morgan's data on why people retire earlier than expected and discuss how to prepare for the unexpected. Learn why having a solid backup plan is essential and what steps you can take to protect your financial future, even if your retirement timeline changes. If you're thinking, "I lo...

In this episode, we tackle Kay's questions about managing her IRA and Roth accounts in retirement. With significant assets, no LTC insurance, and children in differing financial circumstances, Kay wants to minimize taxes while preparing for required minimum distributions (RMDs) and long-term care expenses. We explore the pros and cons of massive Roth conversions, the impact of IRMAA on Medicare pr...

Retirement can be stressful, especially when the markets are unpredictable. In this episode, we'll talk about a simple strategy to give you peace of mind and financial stability in retirement. You'll learn how to set aside five years of income to avoid selling investments during market downturns, create a clear plan for where your money will come from, and adjust your approach based on your comfor...

Today's episode is part rant, part answer to Mike's question about the high cost of prescription drugs under Medicare Part D. We dive into why these costs are so steep, explore alternatives like Canadian pharmacies, and discuss what you can do to manage healthcare expenses in retirement. If you're thinking, "I love the Big Picture Retirement podcast!" please consider rating and reviewing this show...

Financial planning often feels like a numbers game—follow the math, and you'll make the best decisions, right? But what happens when the spreadsheet says one thing, and your peace of mind says another? In this episode, we share the personal story of why Devin and his wife chose to pay off nearly $500,000 in debt, despite the numbers telling them not to. We explore the emotional cost of debt, the v...