Big Picture Retirement®
Planning for, or already enjoying, your retirement? This is the show for you. The success of your retirement hinges on how well you connect the dots between legal, tax, and financial planning. Join your hosts John Ross, JD and Devin Carroll, CFP® as they dig beneath the surface to help you gain the confidence and clarity needed to navigate your retirement journey successfully.
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Inbox Questions | IRA Income & Medicaid Eligibility: Will Too Much Disqualify You?
02/27/2025
Inbox Questions | IRA Income & Medicaid Eligibility: Will Too Much Disqualify You?
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 specific tax, legal, or financial advice, you can engage Devin or John through their individual firms. Contact Devin’s team at Contact John’s team at 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 to the “ratings and reviews” section, tap to rate with five stars, and select “Write a Review.” Then be sure to let us know what you loved most about the episode! Also, if you haven’t done so already, follow the podcast. We add new content every week, and if you’re not following, you’ll likely miss out. Follow now! Don’t miss the Big Picture Retirement Planning Cheat Sheet. We've distilled the essential brackets, thresholds, and rules of retirement into an easy-to-digest, three-page summary. Want to ask Devin or John your question? Just visit and click on the “Ask A Question” menu selection.
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REPLAY | 5 Things Nobody Tells You About Retirement
02/24/2025
REPLAY | 5 Things Nobody Tells You About Retirement
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 and the most impactful. Being unprepared for this could have significant consequences, so make sure you are ready for this. 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 to the “ratings and reviews” section, tap to rate with five stars, and select “Write a Review.” Then be sure to let us know what you loved most about the episode! Also, if you haven’t done so already, follow the podcast. We add new content every week, and if you’re not following, you’ll likely miss out. Follow now! Don’t miss the Big Picture Retirement Planning Cheat Sheet. We've distilled the essential brackets, thresholds, and rules of retirement into an easy-to-digest, three-page summary. Want to ask Devin or John your question? Just visit and click on the “Ask A Question” menu selection. 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 Contact John’s team at
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Inbox Questions | Should We Consider Roth Conversions with a High Income?
02/20/2025
Inbox Questions | Should We Consider Roth Conversions with a High Income?
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 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 to the “ratings and reviews” section, tap to rate with five stars, and select “Write a Review.” Then be sure to let us know what you loved most about the episode! Also, if you haven’t done so already, follow the podcast. We add new content every week, and if you’re not following, you’ll likely miss out. Follow now! Don’t miss the Big Picture Retirement Planning Cheat Sheet. We've distilled the essential brackets, thresholds, and rules of retirement into an easy-to-digest, three-page summary. Want to ask Devin or John your question? Just visit and click on the “Ask A Question” menu selection. 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 Contact John’s team at
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What Happens to Your Crypto When You Die? Estate Planning for Digital Assets
02/17/2025
What Happens to Your Crypto When You Die? Estate Planning for Digital Assets
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 to the “ratings and reviews” section, tap to rate with five stars, and select “Write a Review.” Then be sure to let us know what you loved most about the episode! Also, if you haven’t done so already, follow the podcast. We add new content every week, and if you’re not following, you’ll likely miss out. Follow now! Don’t miss the Big Picture Retirement Planning Cheat Sheet. We've distilled the essential brackets, thresholds, and rules of retirement into an easy-to-digest, three-page summary. Want to ask Devin or John your question? Just visit and click on the “Ask A Question” menu selection. 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 Contact John’s team at
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Inbox Questions | Cryonics and Trusts: Planning for a Future You?
02/13/2025
Inbox Questions | Cryonics and Trusts: Planning for a Future You?
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 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 to the “ratings and reviews” section, tap to rate with five stars, and select “Write a Review.” Then be sure to let us know what you loved most about the episode! Also, if you haven’t done so already, follow the podcast. We add new content every week, and if you’re not following, you’ll likely miss out. Follow now! Don’t miss the Big Picture Retirement Planning Cheat Sheet. We've distilled the essential brackets, thresholds, and rules of retirement into an easy-to-digest, three-page summary. Want to ask Devin or John your question? Just visit and click on the “Ask A Question” menu selection. 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 Contact John’s team at
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The 4 Mindsets That Shape Your Retirement Success
02/10/2025
The 4 Mindsets That Shape Your Retirement Success
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 your mindset and build a strategy for long-term success. 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 to the “ratings and reviews” section, tap to rate with five stars, and select “Write a Review.” Then be sure to let us know what you loved most about the episode! Also, if you haven’t done so already, follow the podcast. We add new content every week, and if you’re not following, you’ll likely miss out. Follow now! Don’t miss the Big Picture Retirement Planning Cheat Sheet. We've distilled the essential brackets, thresholds, and rules of retirement into an easy-to-digest, three-page summary. Want to ask Devin or John your question? Just visit and click on the “Ask A Question” menu selection. 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 Contact John’s team at
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Inbox Questions | Why Use Your IRA First for Long-Term Care Expenses?
02/06/2025
Inbox Questions | Why Use Your IRA First for Long-Term Care Expenses?
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 -- move toward a confident retirement. Just scroll down to the “ratings and reviews” section, tap to rate with five stars, and select “Write a Review.” Then be sure to let us know what you loved most about the episode! Also, if you haven’t done so already, follow the podcast. We add new content every week, and if you’re not following, you’ll likely miss out. Follow now! Don’t miss the Big Picture Retirement Planning Cheat Sheet. We've distilled the essential brackets, thresholds, and rules of retirement into an easy-to-digest, three-page summary. Want to ask Devin or John your question? Just visit and click on the “Ask A Question” menu selection. 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 Contact John’s team at
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Tariffs: Balancing the Pros and Cons
02/03/2025
Tariffs: Balancing the Pros and Cons
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 up consumer costs, and even transform entire industries, like the U.S. auto market. Whether you're curious about the economic trade-offs or the quirky history of a chicken trade war, this episode has you covered! 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 to the “ratings and reviews” section, tap to rate with five stars, and select “Write a Review.” Then be sure to let us know what you loved most about the episode! Also, if you haven’t done so already, follow the podcast. We add new content every week, and if you’re not following, you’ll likely miss out. Follow now! Don’t miss the Big Picture Retirement Planning Cheat Sheet. We've distilled the essential brackets, thresholds, and rules of retirement into an easy-to-digest, three-page summary. Want to ask Devin or John your question? Just visit and click on the “Ask A Question” menu selection. 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 Contact John’s team at
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Inbox Questions | Should Early Social Security Factor Into Retirement Calculations?
01/30/2025
Inbox Questions | Should Early Social Security Factor Into Retirement Calculations?
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 in to explore how Social Security timing fits into a Big Picture retirement strategy and hear our take on Joe’s approach. 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 to the “ratings and reviews” section, tap to rate with five stars, and select “Write a Review.” Then be sure to let us know what you loved most about the episode! Also, if you haven’t done so already, follow the podcast. We add new content every week, and if you’re not following, you’ll likely miss out. Follow now! Don’t miss the Big Picture Retirement Planning Cheat Sheet. We've distilled the essential brackets, thresholds, and rules of retirement into an easy-to-digest, three-page summary. Want to ask Devin or John your question? Just visit and click on the “Ask A Question” menu selection. 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 Contact John’s team at
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Supreme Court Ruling: The Hidden Risks in Life-Insurance Buy-Sell Agreements
01/27/2025
Supreme Court Ruling: The Hidden Risks in Life-Insurance Buy-Sell Agreements
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 avoid unexpected estate tax burdens. We'll explore alternatives like cross-purchase agreements and address key considerations for life insurance ownership. Don’t miss this discussion for business owners and advisors alike! 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 to the “ratings and reviews” section, tap to rate with five stars, and select “Write a Review.” Then be sure to let us know what you loved most about the episode! Also, if you haven’t done so already, follow the podcast. We add new content every week, and if you’re not following, you’ll likely miss out. Follow now! Don’t miss the Big Picture Retirement Planning Cheat Sheet. We've distilled the essential brackets, thresholds, and rules of retirement into an easy-to-digest, three-page summary. Want to ask Devin or John your question? Just visit and click on the “Ask A Question” menu selection. 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 Contact John’s team at
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Inbox Questions | Will GPO Repeal Affect My Benefits?
01/24/2025
Inbox Questions | Will GPO Repeal Affect My Benefits?
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 might affect your benefits, this episode is packed with answers and insights. 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 to the “ratings and reviews” section, tap to rate with five stars, and select “Write a Review.” Then be sure to let us know what you loved most about the episode! Also, if you haven’t done so already, follow the podcast. We add new content every week, and if you’re not following, you’ll likely miss out. Follow now! Don’t miss the Big Picture Retirement Planning Cheat Sheet. We've distilled the essential brackets, thresholds, and rules of retirement into an easy-to-digest, three-page summary. Want to ask Devin or John your question? Just visit and click on the “Ask A Question” menu selection. 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 Contact John’s team at
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The Unexpected Early Retirement
01/20/2025
The Unexpected Early Retirement
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 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 to the “ratings and reviews” section, tap to rate with five stars, and select “Write a Review.” Then be sure to let us know what you loved most about the episode! Also, if you haven’t done so already, follow the podcast. We add new content every week, and if you’re not following, you’ll likely miss out. Follow now! Don’t miss the Big Picture Retirement Planning Cheat Sheet. We've distilled the essential brackets, thresholds, and rules of retirement into an easy-to-digest, three-page summary. Want to ask Devin or John your question? Just visit and click on the “Ask A Question” menu selection. 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 Contact John’s team at
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Inbox Questions | Reducing Taxes and Managing RMDs
01/16/2025
Inbox Questions | Reducing Taxes and Managing RMDs
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 premiums, and other strategies for keeping income taxes as low as possible. 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 to the “ratings and reviews” section, tap to rate with five stars, and select “Write a Review.” Then be sure to let us know what you loved most about the episode! Also, if you haven’t done so already, follow the podcast. We add new content every week, and if you’re not following, you’ll likely miss out. Follow now! Don’t miss the Big Picture Retirement Planning Cheat Sheet. We've distilled the essential brackets, thresholds, and rules of retirement into an easy-to-digest, three-page summary. Want to ask Devin or John your question? Just visit and click on the “Ask A Question” menu selection. 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 Contact John’s team at
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A Smarter Way to Manage Retirement Income
01/13/2025
A Smarter Way to Manage Retirement Income
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 comfort with risk. This straightforward method helps you stay on track, worry less, and enjoy the retirement you’ve worked so hard for. 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 to the “ratings and reviews” section, tap to rate with five stars, and select “Write a Review.” Then be sure to let us know what you loved most about the episode! Also, if you haven’t done so already, follow the podcast. We add new content every week, and if you’re not following, you’ll likely miss out. Follow now! Don’t miss the Big Picture Retirement Planning Cheat Sheet. We've distilled the essential brackets, thresholds, and rules of retirement into an easy-to-digest, three-page summary. Want to ask Devin or John your question? Just visit and click on the “Ask A Question” menu selection. 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 Contact John’s team at
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Inbox Questions | Prescription Prices: A Rant and a Response
01/09/2025
Inbox Questions | Prescription Prices: A Rant and a Response
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! This helps us support more people -- just like you -- move toward a confident retirement. Just scroll down to the “ratings and reviews” section, tap to rate with five stars, and select “Write a Review.” Then be sure to let us know what you loved most about the episode! Also, if you haven’t done so already, follow the podcast. We add new content every week, and if you’re not following, you’ll likely miss out. Follow now! Don’t miss the Big Picture Retirement Planning Cheat Sheet. We've distilled the essential brackets, thresholds, and rules of retirement into an easy-to-digest, three-page summary. Want to ask Devin or John your question? Just visit and click on the “Ask A Question” menu selection. 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 Contact John’s team at
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Smart Financial Planning: Balancing Data with Peace of Mind
01/06/2025
Smart Financial Planning: Balancing Data with Peace of Mind
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 value of financial freedom, and how to balance logic with what truly feels right. 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 to the “ratings and reviews” section, tap to rate with five stars, and select “Write a Review.” Then be sure to let us know what you loved most about the episode! Also, if you haven’t done so already, follow the podcast. We add new content every week, and if you’re not following, you’ll likely miss out. Follow now! Don’t miss the Big Picture Retirement Planning Cheat Sheet. We've distilled the essential brackets, thresholds, and rules of retirement into an easy-to-digest, three-page summary. Want to ask Devin or John your question? Just visit and click on the “Ask A Question” menu selection. 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 Contact John’s team at
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Inbox Questions | When Should You Stop Using TurboTax?
01/02/2025
Inbox Questions | When Should You Stop Using TurboTax?
Today, we tackle a question many retirees face: Can you manage your taxes with DIY software like TurboTax, or is it time to bring in a professional? We'll explore the challenges of navigating tax complexities in retirement, including 401(k) rollovers, RMDs, and other scenarios that could make filing trickier than expected. 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 to the “ratings and reviews” section, tap to rate with five stars, and select “Write a Review.” Then be sure to let us know what you loved most about the episode! Also, if you haven’t done so already, follow the podcast. We add new content every week, and if you’re not following, you’ll likely miss out. Follow now! Don’t miss the Big Picture Retirement Planning Cheat Sheet. We've distilled the essential brackets, thresholds, and rules of retirement into an easy-to-digest, three-page summary. Want to ask Devin or John your question? Just visit and click on the “Ask A Question” menu selection. 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 Contact John’s team at
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Inbox Questions | When Should You Use An LLC?
12/20/2024
Inbox Questions | When Should You Use An LLC?
We answer a question from a 44-year-old Pittsburgh bus driver earning over six figures annually who maxes out a Roth IRA, contributes 10.5% to a 457 plan, and is covered by a pension. He owns five rental properties in his name and wonders if and when he should transfer them to an LLC. 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 to the “ratings and reviews” section, tap to rate with five stars, and select “Write a Review.” Then be sure to let us know what you loved most about the episode! Also, if you haven’t done so already, follow the podcast. We add new content every week, and if you’re not following, you’ll likely miss out. Follow now! Don’t miss the Big Picture Retirement Planning Cheat Sheet. We've distilled the essential brackets, thresholds, and rules of retirement into an easy-to-digest, three-page summary. Want to ask Devin or John your question? Just visit and click on the “Ask A Question” menu selection. 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 Contact John’s team at
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5 Reasons 2025 Could Be a Turbulent Year for Stocks
12/16/2024
5 Reasons 2025 Could Be a Turbulent Year for Stocks
Could 2025 be a stormy year for the stock market? In this episode, we explore five potential triggers that could send markets into turmoil. From the unpredictability of Trump-era “tape bombs” to a potential bursting of the AI bubble, we break down the risks investors should watch for. We also examine how protectionist trade policies, signs of an economic slowdown, and a possible Federal Reserve policy pivot could create turbulence. If you're looking to stay ahead of the curve and prepare for what’s next, this is the episode for you. 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 to the “ratings and reviews” section, tap to rate with five stars, and select “Write a Review.” Then be sure to let us know what you loved most about the episode! Also, if you haven’t done so already, follow the podcast. We add new content every week, and if you’re not following, you’ll likely miss out. Follow now! Don’t miss the Big Picture Retirement Planning Cheat Sheet. We've distilled the essential brackets, thresholds, and rules of retirement into an easy-to-digest, three-page summary. Want to ask Devin or John your question? Just visit and click on the “Ask A Question” menu selection. 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 Contact John’s team at
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Inbox Questions | Capital Gains on the Sale of Home
12/12/2024
Inbox Questions | Capital Gains on the Sale of Home
Today, we tackle a question from Patrick about the nuances of capital gains taxes on the sale of a primary residence. We break down how community property laws can impact your tax liability, the role of improvements in calculating your cost basis, and other key considerations to keep in mind when selling your home. 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 to the “ratings and reviews” section, tap to rate with five stars, and select “Write a Review.” Then be sure to let us know what you loved most about the episode! Also, if you haven’t done so already, follow the podcast. We add new content every week, and if you’re not following, you’ll likely miss out. Follow now! Don’t miss the Big Picture Retirement Planning Cheat Sheet. We've distilled the essential brackets, thresholds, and rules of retirement into an easy-to-digest, three-page summary. Want to ask Devin or John your question? Just visit and click on the “Ask A Question” menu selection. 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 Contact John’s team at
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What Trump’s Tax Policies Mean for Your Retirement
12/09/2024
What Trump’s Tax Policies Mean for Your Retirement
How could Trump’s tax policies impact your retirement plans? In this episode, we break down the potential changes, from tax cuts to shifting brackets, and discuss what they could mean for your savings, Social Security, and investment strategies. 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 to the “ratings and reviews” section, tap to rate with five stars, and select “Write a Review.” Then be sure to let us know what you loved most about the episode! Also, if you haven’t done so already, follow the podcast. We add new content every week, and if you’re not following, you’ll likely miss out. Follow now! Don’t miss the Big Picture Retirement Planning Cheat Sheet. We've distilled the essential brackets, thresholds, and rules of retirement into an easy-to-digest, three-page summary. Want to ask Devin or John your question? Just visit and click on the “Ask A Question” menu selection. 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 Contact John’s team at
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BOI Reporting Delayed: The Future of the Corporate Transparency Act
12/05/2024
BOI Reporting Delayed: The Future of the Corporate Transparency Act
In this episode, we’re diving into the latest legal drama surrounding the Corporate Transparency Act (CTA). A federal judge in Texas has temporarily blocked this law, which would have required U.S. businesses to report detailed information about their stakeholders to the government. What does this mean for business owners? Is this a win for small businesses or just a delay in the inevitable? We'll break down the law, the court’s decision, and what might happen next—all in plain English. 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 to the “ratings and reviews” section, tap to rate with five stars, and select “Write a Review.” Then be sure to let us know what you loved most about the episode! Also, if you haven’t done so already, follow the podcast. We add new content every week, and if you’re not following, you’ll likely miss out. Follow now! Don’t miss the Big Picture Retirement Planning Cheat Sheet. We've distilled the essential brackets, thresholds, and rules of retirement into an easy-to-digest, three-page summary. Want to ask Devin or John your question? Just visit and click on the “Ask A Question” menu selection. 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 Contact John’s team at
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What Your Will WON’T Do
11/04/2024
What Your Will WON’T Do
In this episode, we’re breaking down common myths about what a Will can actually take care of. A lot of people think a will covers everything, but it’s not that simple! We’ll explain how probate works, why some assets don’t go through your will, and what your will can’t control — like retirement accounts or jointly owned property. We’ll also talk about other tools you might need to make sure your plans really happen the way you want. Join us to learn what your will really does and avoid surprises for your family down the road. 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 to the “ratings and reviews” section, tap to rate with five stars, and select “Write a Review.” Then be sure to let us know what you loved most about the episode! Also, if you haven’t done so already, follow the podcast. We add new content every week, and if you’re not following, you’ll likely miss out. Follow now! Don’t miss the Big Picture Retirement Planning Cheat Sheet. We've distilled the essential brackets, thresholds, and rules of retirement into an easy-to-digest, three-page summary. Want to ask Devin or John your question? Just visit and click on the “Ask A Question” menu selection. 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 Contact John’s team at
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5 Ways to Make Your Retirement Recession-Ready
10/29/2024
5 Ways to Make Your Retirement Recession-Ready
In this episode, we break down simple strategies to protect your retirement savings when the market gets rough. We’ll start with why staying calm is key and how planning ahead can help you avoid emotional decisions. You'll learn how to match your investments with both your comfort level and your financial goals, plus why a balanced mix and a short-term “spending bucket” can keep you from selling at the wrong time. We’ll also cover how fees impact your savings and why it’s worth checking if they’re delivering good value. Finally, we’ll share the benefits of regularly reviewing your plan and how smart tax strategies can give you a boost during downturns. 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 to the “ratings and reviews” section, tap to rate with five stars, and select “Write a Review.” Then be sure to let us know what you loved most about the episode! Also, if you haven’t done so already, follow the podcast. We add new content every week, and if you’re not following, you’ll likely miss out. Follow now! Don’t miss the Big Picture Retirement Planning Cheat Sheet. We've distilled the essential brackets, thresholds, and rules of retirement into an easy-to-digest, three-page summary. Want to ask Devin or John your question? Just visit and click on the “Ask A Question” menu selection. 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 Contact John’s team at
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Is Downsizing Right for Your Retirement?
10/21/2024
Is Downsizing Right for Your Retirement?
Today we discuss the pros and cons of downsizing in retirement. We discuss how selling your home can reduce expenses, simplify your lifestyle, and free up money for travel or investments. But we also cover the potential downsides, like emotional attachment to your family home and the hidden costs of moving. Tune in to help decide if downsizing is the right move for you. 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 to the “ratings and reviews” section, tap to rate with five stars, and select “Write a Review.” Then be sure to let us know what you loved most about the episode! Also, if you haven’t done so already, follow the podcast. We add new content every week, and if you’re not following, you’ll likely miss out. Follow now! Don’t miss the Big Picture Retirement Planning Cheat Sheet. We've distilled the essential brackets, thresholds, and rules of retirement into an easy-to-digest, three-page summary. Want to ask Devin or John your question? Just visit and click on the “Ask A Question” menu selection. 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 Contact John’s team at
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How Long Will I Live? Planning for Longevity in Retirement
10/14/2024
How Long Will I Live? Planning for Longevity in Retirement
In this episode, we talk about an important part of retirement planning that many people overlook—figuring out how long you might live. We explain why using average life expectancy or guessing based on family history can be risky, and why it’s important to plan for a longer life. We also share tools that can help you estimate how long your savings need to last, whether you’re planning on your own or with a partner. Making a solid plan for how long you’ll need your money is key to a secure retirement. Resources to use: Actuaries Longevity Illustrator (ALI) SSA Life Expectancy Calculator 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 to the “ratings and reviews” section, tap to rate with five stars, and select “Write a Review.” Then be sure to let us know what you loved most about the episode! Also, if you haven’t done so already, follow the podcast. We add new content every week, and if you’re not following, you’ll likely miss out. Follow now! Don’t miss the Big Picture Retirement Planning Cheat Sheet. We've distilled the essential brackets, thresholds, and rules of retirement into an easy-to-digest, three-page summary. Want to ask Devin or John your question? Just visit and click on the “Ask A Question” menu selection. 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 Contact John’s team at
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3 Ways to Pay for Long-Term Care
10/07/2024
3 Ways to Pay for Long-Term Care
Long-term care is a reality that many retirees will face, but the question is—how will you pay for it? In this episode, we break down the three primary ways to cover long-term care expenses. We’ll walk you through the pros and cons of each option and explain why planning ahead is critical. Plus, we’ll introduce a tool that can help you estimate the actual costs of care in your area. Whether you’re planning for yourself or a loved one, this episode will give you the insights you need to make an informed decision about long-term care expenses. 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 to the “ratings and reviews” section, tap to rate with five stars, and select “Write a Review.” Then be sure to let us know what you loved most about the episode! Also, if you haven’t done so already, follow the podcast. We add new content every week, and if you’re not following, you’ll likely miss out. Follow now! Don’t miss the Big Picture Retirement Planning Cheat Sheet. We've distilled the essential brackets, thresholds, and rules of retirement into an easy-to-digest, three-page summary. Want to ask Devin or John your question? Just visit and click on the “Ask A Question” menu selection. 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 Contact John’s team at
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Monte Carlo Simulations: Is Your “Probability of Success” Trustworthy?
09/30/2024
Monte Carlo Simulations: Is Your “Probability of Success” Trustworthy?
In this episode, we take a closer look at Monte Carlo simulations—a tool used in retirement planning to estimate your chances of success. But are those percentages really reliable? Can an 85% or 90% success rate give you confidence in your retirement plan? We’ll explain how these simulations work, how different assumptions can lead to very different results, and why you shouldn’t just rely on past returns. 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 to the “ratings and reviews” section, tap to rate with five stars, and select “Write a Review.” Then be sure to let us know what you loved most about the episode! Also, if you haven’t done so already, follow the podcast. We add new content every week, and if you’re not following, you’ll likely miss out. Follow now! Don’t miss the Big Picture Retirement Planning Cheat Sheet. We've distilled the essential brackets, thresholds, and rules of retirement into an easy-to-digest, three-page summary. Want to ask Devin or John your question? Just visit and click on the “Ask A Question” menu selection. 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 Contact John’s team at
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The Stock Market Gamble Most Investors Lose
09/23/2024
The Stock Market Gamble Most Investors Lose
In this episode, we explore the realities of stock-picking, revealing that it’s a gamble where the odds are heavily stacked against the average investor. Studies show that most individual stocks underperform or lose value over time, so we make a strong case for the smarter and more reliable approach. 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 to the “ratings and reviews” section, tap to rate with five stars, and select “Write a Review.” Then be sure to let us know what you loved most about the episode! Also, if you haven’t done so already, follow the podcast. We add new content every week, and if you’re not following, you’ll likely miss out. Follow now! Don’t miss the Big Picture Retirement Planning Cheat Sheet. We've distilled the essential brackets, thresholds, and rules of retirement into an easy-to-digest, three-page summary. Want to ask Devin or John your question? Just visit and click on the “Ask A Question” menu selection. 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 Contact John’s team at
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How Kamala Harris’s Housing Plan Could Drastically Change Wealth Transfer
09/16/2024
How Kamala Harris’s Housing Plan Could Drastically Change Wealth Transfer
In this episode, we unpack Vice President Kamala Harris’s ambitious plan to lower housing costs, which would be funded by adopting Senator Elizabeth Warren’s sweeping estate tax overhaul. We explore the major changes proposed, including reducing the estate tax exclusion to $3.5 million, significantly increasing estate tax rates, and imposing new restrictions on popular estate planning tools like GRATs and grantor trusts. We also discuss the broader implications of these changes, such as the potential impact on wealth transfer strategies and the generational transfer of 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 -- move toward a confident retirement. Just scroll down to the “ratings and reviews” section, tap to rate with five stars, and select “Write a Review.” Then be sure to let us know what you loved most about the episode! Also, if you haven’t done so already, follow the podcast. We add new content every week, and if you’re not following, you’ll likely miss out. Follow now! Don’t miss the Big Picture Retirement Planning Cheat Sheet. We've distilled the essential brackets, thresholds, and rules of retirement into an easy-to-digest, three-page summary. Want to ask Devin or John your question? Just visit and click on the “Ask A Question” menu selection. 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 Contact John’s team at
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