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.

Inbox Question | Roth Conversion Strategy for High Earners 11/13/2025

Is This the Worst Time to Retire? 3 Ways to Prepare (Just in Case) 11/10/2025

Inbox Question | Typical Costs of Estate Planning 11/06/2025

The Hidden Cost of Delaying Social Security 11/03/2025

Inbox Question | What’s the Big Deal with HSAs 10/30/2025

Inbox Question | Using IRA Withdrawals to Fund Daughter’s Roth 10/16/2025

The Great Retirement Plan Illusion 10/06/2025

The Hidden Estate Tax Lesson in the $1.8 Billion Powerball 09/29/2025

Why So Many Americans Are Claiming Social Security Early in 2025 09/22/2025

Three Priorities That Should Shape Your Social Security Decision 09/01/2025

Three Priorities That Should Shape Your Social Security Decision When should you claim Social Security? For high-net-worth retirees, this is not a simple decision. In this episode, we explain why Social Security is not just a monthly check but a strategic part of a well-built retirement plan. Devin begins by challenging the common belief that wealthy retirees do not need to think about Social Security. In reality, those with more assets often have more choices, and those choices make the timing decision even more important. You will learn about the three core priorities that should guide how and when you file: protecting a surviving spouse, maximizing guaranteed income, and coordinating Social Security with the rest of your retirement plan. Devin explains how each of these goals can shape your filing strategy and why getting the timing right can support better outcomes for both income and taxes. This episode also covers how delaying benefits can increase lifetime income for a surviving spouse, reduce tax burdens through coordinated withdrawals, and help create a stronger income floor that is not tied to the markets. If you have flexibility in when you file, use it wisely. Social Security decisions should support your long-term goals, reflect your income needs, and fit within your overall tax and investment strategy. 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. /episode/index/show/bigpictureretirement/id/38038720

What Millionaire Retirees Fear Most (But Rarely Talk About) 08/25/2025

What Millionaire Retirees Fear Most (But Rarely Talk About) For many affluent retirees, the biggest financial fear isn’t market volatility or rising taxes. It’s this simple question: What happens if I’m not the one here to manage the plan? In this episode, we talk about a deeply personal concern shared by countless couples. When one spouse manages the investment strategy, the tax planning, and the long-term vision, the other is often left trusting that everything will work out. That trust may work fine today, but what if something changes tomorrow? What if the surviving spouse is left with a complex financial plan they don’t fully understand? Devin shares his own story, including the moment he realized his wife might struggle to carry on the plan they had built together. From that fear came action; a series of steps to make sure she would not only inherit assets, but also confidence and clarity. You’ll hear about the simple, practical moves you can make to protect the person you love, including how to start the conversation, what to document, and how to choose someone you both trust. This episode is a must-listen if you’ve ever thought, I just want to make sure my spouse will be okay if something happens to me. 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. /episode/index/show/bigpictureretirement/id/37942760

Private Equity Meets Your 401(k) 08/18/2025

Private Equity Meets Your 401(k) Should everyday investors be allowed to hold private equity, venture capital, or even crypto in their 401(k)s? A new executive order suggests it might soon be possible. In this episode, we walk through the real implications of this move, especially for retirement savers who may not be equipped to handle the risks. We start with a quick quiz that highlights a troubling truth: most 401(k)-only investors don’t understand basic financial principles like compound interest, inflation, or diversification. If many people struggle with the fundamentals, what happens when we layer in high-fee, illiquid, and opaque investments? You'll hear what’s already allowed in retirement plans, why private equity firms are pushing for broader access, and what dangers exist when complexity is added to accounts that are supposed to be simple and secure. We share a personal example from our own experience with illiquid private investments and explain why adding these as standalone options could backfire for plan participants. This episode also explores why this change might be happening now, what fiduciaries need to consider, and why protecting investors requires more than just offering new choices. It requires clear guidance, thoughtful planning, and honest conversations about financial literacy. 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. /episode/index/show/bigpictureretirement/id/37857820

5 Mistake Most Millionaire Retirees Make 07/21/2025

Overview of the One, Big, Beautiful Bill 07/14/2025

Inbox Question | How Filing Early Impacts the Spousal Benefit 07/03/2025

Why Taxes In Retirement Get More Complicated 06/24/2025

Inbox Question | The Good Life Abroad: Would We Go? 06/19/2025

Inbox Question | How Much Umbrella Insurance Do You Need? 06/05/2025

Inbox Question | How the Small Estate Affidavit Process Works 05/29/2025

Listener Q&A: Trusts, IRMAA, Inheritance Taxes, Capital Gains, and More 05/26/2025

Listener Q&A: Trusts, IRMAA, Inheritance Taxes, Capital Gains, and More 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 taxable? Capital Gains on a Vacation Home – Should you delay estate planning until after the sale of a property? What about the "2 out of 5 years" exemption? Paying Inheritance Taxes – If all your accounts list beneficiaries, how will state inheritance taxes (like Pennsylvania's) get paid on time? Step-Up in Basis with TOD Deeds – In Oklahoma, does property with a Transfer on Death deed still receive a step-up in basis? Impact of Home Sale on IRMAA and Roth Conversions – How does selling a vacation home affect your income-based Medicare premiums and Roth conversion strategies? Medicare Enrollment Rules at Age 65 – Are you legally required to enroll in Medicare at 65 if not on a qualifying employer plan? Trusts and Anonymity – How can you use estate planning tools while keeping your affairs private and self-directed? Probate Friendliness by State – Which states make probate easy, and which ones almost demand a trust-based plan? Inherited IRAs and Roth Conversions – Can a beneficiary convert inherited IRA funds into a Roth IRA for future tax-free growth? If you’ve ever had a nuanced question about retirement or estate planning, chances are someone else has too—and we’re tackling them head-on in this packed Q&A episode. 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. /episode/index/show/bigpictureretirement/id/36709735

The 3 Parts to a Perfect Estate Plan – Part 3: Protecting the Beneficiaries’ Inheritance (Estate Planning Series Finale) 05/19/2025

The 3 Parts to a Perfect Estate Plan – Part 3: Protecting the Beneficiaries’ Inheritance (Estate Planning Series Finale) 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 how to: Safeguard inheritances from a beneficiary’s divorce or personal liabilities Provide for special needs or disabled heirs without jeopardizing government benefits Handle contingency planning, including what happens if a beneficiary predeceases you Protect minor children using trusts instead of relying on court-supervised guardianships We also highlight common mistakes—like failing to update your estate plan after major life events—and share practical steps to avoid them. 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. /episode/index/show/bigpictureretirement/id/36619345

Inbox Question | Home Equity for Long Term Care 05/15/2025

The 3 Parts to a Perfect Estate Plan – Part 2c: Common Mistakes & Oversights 05/12/2025

Inbox Question | Medicaid for Parents 05/08/2025

The 3 Parts to a Perfect Estate Plan – Part 2b: Tax Considerations 05/05/2025

Inbox Question | Company Stock in 401K 05/01/2025

The 3 Parts to a Perfect Estate Plan: Part 2a: Non-Probate Transfers 04/28/2025

Inbox Question | Running a Business & Collecting Benefits: What Counts Toward the Earnings Limit? 04/24/2025

The 3 Parts to a Perfect Estate Plan – Part 1b: Planning for Incapacity 04/21/2025

The 3 Parts to a Perfect Estate Plan – Part 1b: Planning for Incapacity 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 📍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. /episode/index/show/bigpictureretirement/id/36239555

The 3 Parts to a Perfect Estate Plan – Part 1a: Planning for Incapacity 04/14/2025

The 3 Parts to a Perfect Estate Plan – Part 1a: Planning for Incapacity 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 📍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. /episode/index/show/bigpictureretirement/id/36121660

Big Picture Retirement®

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