Episodes

  • The 3 Parts to a Perfect Estate Plan: Part 2a: Non-Probate Transfers
    Apr 28 2025

    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 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!” 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. https://www.carrolladvisory.com/pl/2148282517

    Want to ask Devin or John your question? Just visit https://www.bigpictureretirement.com/ and click on the “Ask A Question” menu selection.

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    27 mins
  • Inbox Question | Running a Business & Collecting Benefits: What Counts Toward the Earnings Limit?
    Apr 24 2025

    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 team at https://www.rossandshoalmire.com/

    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. https://www.carrolladvisory.com/pl/2148282517

    Want to ask Devin or John your question? Just visit https://www.bigpictureretirement.com/ and click on the “Ask A Question” menu selection.

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    7 mins
  • The 3 Parts to a Perfect Estate Plan – Part 1b: Planning for Incapacity
    Apr 21 2025

    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 private pay, long-term care insurance, or Medicaid planning.

    We’ll also highlight common pitfalls like outdated or missing Powers of Attorney, and the risks of DIY estate planning that can create real problems down the road.

    If you haven’t reviewed your incapacity planning documents lately—or if you’ve never had them in place—this episode is your call to action.

    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!” 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. https://www.carrolladvisory.com/pl/2148282517

    Want to ask Devin or John your question? Just visit https://www.bigpictureretirement.com/ and click on the “Ask A Question” menu selection.

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    46 mins
  • The 3 Parts to a Perfect Estate Plan – Part 1a: Planning for Incapacity
    Apr 14 2025

    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 special series to break estate planning down into simple, practical steps. We’ll walk through the essential documents you need, the common mistakes that can derail a plan, and some of the more advanced strategies for protecting and passing on your wealth efficiently.

    Whether you’re starting from scratch or just need to update an existing plan, this series will give you the roadmap you need.

    Now, we originally thought we could cover the first part of this in a single episode—but planning for incapacity turned out to be too important to rush. In this episode, we’ll cover why incapacity planning is essential, real-life scenarios that make it critical, and the foundational documents every adult should have: Financial and Medical Powers of Attorney, and Advance Directives.

    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!” 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. https://www.carrolladvisory.com/pl/2148282517

    Want to ask Devin or John your question? Just visit https://www.bigpictureretirement.com/ and click on the “Ask A Question” menu selection.

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    31 mins
  • Inbox Question | A Better Approach to the S&P 500?
    Mar 20 2025

    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.rossandshoalmire.com/

    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. https://www.carrolladvisory.com/pl/2148282517

    Want to ask Devin or John your question? Just visit https://www.bigpictureretirement.com/ and click on the “Ask A Question” menu selection.

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    8 mins
  • Inbox Question | Cutting Work Hours at 60: Will It Reduce Social Security?
    Mar 13 2025

    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 to miss!

    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!” 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. https://www.carrolladvisory.com/pl/2148282517

    Want to ask Devin or John your question? Just visit https://www.bigpictureretirement.com/ and click on the “Ask A Question” menu selection.

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    5 mins
  • How to Travel Like a Local in Retirement (Not Just a Tourist)
    Mar 10 2025

    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 world

    If you’re looking to travel smarter, go beyond tourist hotspots, and make the most of your retirement years, this conversation is for you!

    📍 Learn more about The Good Life Abroad: https://thegoodlifeabroad.com/

    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!” 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. https://www.carrolladvisory.com/pl/2148282517

    Want to ask Devin or John your question? Just visit https://www.bigpictureretirement.com/ and click on the “Ask A Question” menu selection.

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    36 mins
  • Inbox Question | Tax Treatment of Special Needs Trusts: What You Need to Know
    Mar 6 2025

    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 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!” 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. https://www.carrolladvisory.com/pl/2148282517

    Want to ask Devin or John your question? Just visit https://www.bigpictureretirement.com/ and click on the “Ask A Question” menu selection.

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    10 mins
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