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.

Will A Roth Conversion Save You Taxes? 06/15/2026

The Gift Tax Loophole Congress Wants to Close 06/08/2026

How to Get a Full Step-Up in Basis (Even If You Don’t Live in a Community Property State) 06/02/2026

The Social Security Earnings Limit May Be Eliminated 05/11/2026

What 75 Year Old Retirees Regret Most 05/04/2026

Inbox Question | Leveraged ETFs for Supercharging Retirement Savings 04/23/2026

Inbox Question | QCD from a Workplace Retirement Plan 04/16/2026

You’re Probably Looking at the Wrong Estate Tax 04/06/2026

You’re Probably Looking at the Wrong Estate Tax Unless you’re listening to this while flying in your own Gulfstream, federal estate taxes probably aren’t something you need to worry about. In 2026, they only apply to estates over $15 million, or $30 million for married couples, so they impact a very small percentage of people. But state-level estate and inheritance taxes are a different story. In this episode, we break down how these lesser-known taxes work, which states still impose them, and why they can catch even well-prepared retirees off guard. While many states have eliminated these taxes to keep retirees from leaving, 12 states plus Washington, D.C. still have estate taxes, and five have inheritance taxes. Maryland is the only state that has both. If your goal is to pass on wealth efficiently, where you live could matter more than you think. 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/40740825

Inbox Question | Should I Use A Spendthrift Trust? 04/02/2026

How Your AI Data Could Be Used Against You 03/23/2026

Should a Blood Test Shape Your Retirement Plan? 03/16/2026

Why Recency Bias Is Dangerous for Today’s Retirees 03/09/2026

Five Retirement Loose Ends You Can’t Ignore 02/16/2026

Planning for Single Retirees — Part 4: Long-Term Care, Incapacity, and Estate Planning 02/09/2026

Planning for Single Retirees — Part 4: Long-Term Care, Incapacity, and Estate Planning In this last episode of our Planning for Single Retirees series, we tackle the part of retirement planning that matters most when you don’t have a built-in safety net: what happens if you can’t manage life or money on your own. Today, John is joined by estate planning attorney Lisa Shoalmire to walk through the real-world planning issues facing “senior orphans,” including how to set up financial and medical decision-makers, what to do if you don’t have a trusted family member, and how bank agency accounts and professional care managers can step in when needed. They also cover how isolation increases the risk of scams and exploitation, why consolidating accounts and simplifying your finances matters more as you age, and the estate planning details single retirees should get right now—from probate choices to charitable bequests and protections against bad actors. If you’re single, widowed, divorced, or simply planning without a spouse you can rely on, this episode is about protecting your independence, your dignity, and your plan—before a crisis forces decisions for you. 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/40040600

Planning for Single Retirees — Part 3: Tax Planning and Roth Conversions 02/02/2026

Planning for Single Retirees — Part 3: Tax Planning and Roth Conversions The tax planning process doesn’t change for single retirees—but the margin for error does. In this episode, we explain why taxes behave differently when there’s only one tax bracket, no spousal coordination, and no survivor window to clean things up later. We discuss why IRMAA thresholds hit sooner for single filers and how small income decisions can have outsized consequences. We walk through a simple framework that focuses on understanding your income baseline, where your assets are held, how Medicare premiums factor into tax decisions, and why time horizon matters more when there’s only one lifetime to plan around. This episode isn’t about squeezing out every last tax advantage. It’s about protecting flexibility, avoiding irreversible mistakes, and building a plan that works without a backup. 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/39958160

Planning for Single Retirees — Part 2: Social Security Claiming Decisions 01/26/2026

Planning for Single Retirees — Part 2: Social Security Claiming Decisions For single retirees, Social Security isn’t just another filing decision. It’s the foundation of the entire retirement income plan. In this episode, we explain why claiming decisions matter more when there’s no spouse, no survivor benefit, and no backup income stream. We walk through the four filters we use with single clients, including prior marriages, life expectancy, retirement income needs, and the tradeoffs between delaying Social Security and drawing from investment assets. We also discuss the emotional side of these decisions—fear of running out of money, fear of dying too early, and the pressure of making irreversible choices alone. This episode isn’t about finding the “perfect” strategy. It’s about building a plan you can stick with, even when markets and assumptions don’t cooperate. 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/39873970