Explore every episode of the podcast Big Picture Retirement®

Dolly Parton had hundreds of millions of dollars, sophisticated estate planning, and a plan for what would happen after she was gone. Yet conflict still followed her death. In this episode, we look at what happened and the important lessons it offers about what a good estate plan can accomplish, what it can't prevent, and why even the best planning can't account for everything.

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. 

Stocks are near record highs while fixed-income yields are at levels we haven't seen in nearly 20 years. That combination may give retirees an unusual opportunity—but taking advantage of it requires thinking differently about how a retirement portfolio should be built.

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. 

Smart retirees can still miss important Social Security rules. In this episode, we cover 7 common rules that even well-informed retirees often overlook, and how those blind spots can affect taxes, benefits, and the overall retirement plan.

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. 

Can AI really help you create an estate plan, or could it create problems your family won't discover until it's too late?

In this episode, we review a real Texas will and uncover several surprising issues involving beneficiary requirements, executor compensation, and a Lady Bird deed.

It's a practical look at where AI can help with estate planning, where it can fall short, and why understanding what you're signing matters.

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. 

Do retirees actually run out of money? After reading hundreds of real retirement stories from people who did, one pattern became clear: it usually wasn't poor investing that caused the problem. In this episode, we discuss the six most common reasons retirement plans fail and what you can do now to protect yourself. 

Use our free retirement stress test assessment tool https://www.carrolladvisory.com/pl/2148821257 

Title: 7 Social Security Rules Every Retiree Needs to Know

Description: Smart retirees can still miss important Social Security rules. In this episode, we cover 7 common rules that even well-informed retirees often overlook, and how those blind spots can affect taxes, benefits, and the overall retirement plan.

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. 

Can your brokerage firm actually stop you from accessing your own money? In this episode, we walk through a real case involving a $3 million retirement account, explain when firms are allowed to place a temporary hold, and show you what you can do now to protect your independence.

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. 

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. 

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. 

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. 

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. 

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. 

Kevin asks about using leveraged ETFs (2x and 3x return) for his retirement savings. LEverage

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. 

Ann asks about making qualified charitable distributions from her 457 plan. 

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. 

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 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. 

A listener asks about a spendthrift trust for his adult "airhead" granddaughter. 

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. 

More people are using AI tools every day to ask questions, solve problems, and even talk through personal decisions.

But many users make one dangerous assumption: that their conversations are completely private.

In reality, AI systems collect and process data in ways most people don't fully understand. That information could potentially be stored, analyzed, or used in ways you didn't intend.

In this episode, we discuss how AI platforms handle user data, why you should be careful about what you share, and the simple mindset shift everyone should adopt when using AI tools.

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. 

Advances in predictive medicine are starting to raise a fascinating question: what if we could estimate our longevity with much greater accuracy?

New blood tests and biomarkers are being developed that may help identify risks for diseases years—or even decades—before symptoms appear. Some researchers believe these tools could eventually provide meaningful clues about how long we might live.

If that happens, it could have major implications for retirement planning.

Should information about your potential lifespan influence when you retire, how much you spend, or how you invest?

In this episode, we explore how predictive medicine is evolving, what scientists are learning from advanced blood testing, and whether this kind of information could one day reshape how people plan for retirement.

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. 

Most people assume the future will look like the recent past. That's called recency bias, and it can quietly wreck a retirement plan.

If the market has been strong for years, investors start believing those returns will continue forever. If the market crashes, people assume things will only get worse.

But retirement planning isn't about the last five years. It's about the next thirty.

In this episode, I explain how recency bias influences investment decisions, why it can lead retirees to take the wrong risks at the wrong time, and how to build a retirement plan that works even when the future looks very different from the past.

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. 

Saving for retirement is only half the job. In this episode, we discuss the five financial loose ends that can quietly drain retirement income and why addressing them early creates flexibility and peace of mind.

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. 

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 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. 

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 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. 

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 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. 

Most retirement advice is designed for married couples. But planning for retirement when you're single comes with a very different set of risks and decisions.

In this first episode of a five-part series, we explain why retirement planning changes when there's no spouse to share income, benefits, caregiving, or decision-making. We define what "single" really means in retirement, explore the lack of financial and personal backup, and outline how this affects Social Security, taxes, investment risk, long-term care, and estate planning.

This episode isn't about tactics. It's about mindset. When you're planning alone, the goal isn't perfection. It's resilience. In Part 2, we begin with Social Security, the foundation for many single retirees.

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. 

For many people, retirement feels less like a reward and more like a financial cliff. In this episode, we break down seven key factors that lead to a more financially stable retirement. You'll learn how small, practical decisions can add up to lasting stability, no matter how markets or headlines behave.

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. 

Selling a business isn't just about finding a buyer and shaking hands on the terms — it's about choosing the right structure. In this episode, we break down stock sales, asset sales, common tax traps, and the key details buyers and sellers often overlook.

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. 

Frank is interviewing financial advisors and asks whether it is reasonable to expect them to share client names as references.

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. 

In this episode, we break down the headlines about eliminating the federal income tax, $2,000 tariff-funded checks, and "no taxes below $150,000." We look at the math, the Supreme Court challenges, and what these proposals would actually mean for retirees.

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. 

Scott finds it difficult to manage asset allocation and buckets across multiple accounts and asks for an efficient way to coordinate everything.

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. 

In this episode, Devin and John break down the key tax and retirement planning changes coming in 2026 and what they mean for your income, benefits, and long term strategy. We cover the latest Social Security COLA update, the expected increase to Medicare Part B premiums, and the new Social Security earnings test thresholds. We also walk through the shifting rules around capital gains, the standard deduction, and the return of the SALT cap. For charitable giving, we outline the new above the line deduction, the AGI floor for itemizing, the cap tied to the highest tax rate, and the updated QCD limit of one hundred eleven thousand dollars. If you want to understand how the 2026 landscape could affect your plan, this episode gives you the practical guidance you need.

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. 

In this episode, John talks about the 5 things that he hates to hear from his clients. You will learn why certain statements (and thinking) slow everything down, what your attorney wishes you understood before walking into the meeting, and how to approach your plan with clarity, calm thinking, and realistic expectations. If you want to make better decisions and create an estate plan your family can actually rely on, this episode will point you in the right direction.

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. 

Meera and her husband have $4.5 million in retirement accounts and a $430K income. They want guidance on when to start Roth conversions, how much to convert each year, and whether to continue 401(k) contributions.

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. 

Everyone's wondering if this is the worst time to retire. With high valuations, stubborn inflation, and constant uncertainty, it's easy to feel uneasy about your timing. In this episode, we look at what history teaches from past "lost decades," why the order of returns matters, and how to protect your plan without panic.

You'll learn three ways to prepare just in case: build a spending bucket, stress-test your plan, and rethink your risk exposure. Retirement success isn't about timing the market. It's about preparation and peace of mind.

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. 

David asks for a general idea of what estate planning services typically cost, following up on the six-part podcast series.

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. 

You've heard it a thousand times: "Wait until 70 to file for Social Security." But if that's such obvious advice, why do most retirees file earlier? In this episode, we uncover the hidden cost of waiting and the trade-offs most experts ignore. You'll learn how early withdrawals, taxes, and real-life emotions all change the math—and why the "right" answer isn't the same for everyone.

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. 

Daryl wants a simple explanation of why Health Savings Accounts matter and what makes them such a powerful retirement planning tool.

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. 

John asks if taking larger IRA withdrawals beyond his RMD to fund his daughter's Roth IRA makes sense as a strategy to reduce future RMDs, lower estate taxes, and pass on tax-free assets.

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. 

Many retirees think they have a plan when what they really have is an investment pitch dressed up as planning. This episode uncovers why that illusion is dangerous, the costly mistakes it hides, and how to spot the difference between true planning and portfolio sales.

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. 

Winning the lottery may be rare, but estate tax mistakes aren't. In this episode, we use the recent $1.8 billion Powerball jackpot to highlight how generational wealth can be eroded by estate taxes and how tools like a BDIT can help protect growth assets. We'll also show why this strategy isn't just for lottery winners, but for anyone holding assets with explosive growth potential.

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. 

So far in 2025, early Social Security filings have jumped dramatically compared to last year. Nearly half of those filing early say they're doing so because they're worried about cuts. But will filing early really help? In this episode, we talk about what the data shows, what most people get wrong about Social Security cuts, and how to think about your filing strategy with clarity, not fear. 

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. 

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 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. 

 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 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. 

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 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. 

You've done the hard work. You saved consistently, built a seven-figure portfolio, and are ready to enjoy retirement. But even millionaire retirees can make mistakes that put their plans at risk. In this episode, Devin shares the five most common retirement mistakes he sees among high-net-worth clients. These include missing long-term tax planning opportunities, underestimating healthcare and long-term care costs, failing to plan for success as well as failure, approaching income withdrawals without structure, and overpaying for financial advice. If you want to get the most out of what you've saved, this episode will help you avoid costly missteps and retire with more clarity and control.

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. 

In this episode, we break down the newly signed One Big Beautiful Bill Act (OBBBA) and what it means for retirees. From the extension of the 2017 tax cuts to new rules around Roth conversions, Social Security taxation, and a brand-new "Senior Deduction"—there's a lot packed into this legislation. We'll walk you through the major provisions, highlight how they may affect your retirement income strategy, and share practical planning moves to consider.

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.

Today we answer a question from Ken, a recent retiree at 63, about how his Social Security claiming decision impacts his wife's future spousal benefit. We break down how spousal benefits are calculated, whether the FRA (Full Retirement Age) amount is frozen when you claim early, and how COLA (Cost of Living Adjustments) factor into the equation.

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. 

Most retirees think tax planning ends with knowing their tax bracket, but that's just the beginning. In this episode, we unpack how different income sources interact in retirement, and how seemingly smart decisions can trigger hidden taxes, Medicare surcharges, and other costly surprises. Learn how to avoid the traps and make your retirement income work smarter.

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. 

Today we answer a question from Chris about The Good Life Abroad and whether we plan to take a trip with the company. We share our thoughts on the concept, what interests us about their offerings, and whether a future review might be on the horizon.

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. 

Today we answer a question from Sandi about how much umbrella insurance coverage you really need — especially as you approach retirement. We discuss why someone might choose a $2 million policy, how assets like home value, retirement accounts, and savings factor in, and share real-world examples to help you gauge whether you're over- or underinsured.

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. 

Today we answer a question from Peter about what happens when a parent dies with a fully planned estate that avoids probate — and how the Small Estate Affidavit process works in practice. We discuss handling unexpected estate assets like refund checks, whether you can open an estate bank account without letters testamentary, and who's responsible for final taxes and bills

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. 

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 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.