We answer a question from a 44-year-old Pittsburgh bus driver earning over six figures annually who maxes out a Roth IRA, contributes 10.5% to a 457 plan, and is covered by a pension. He owns five rental properties in his name and wonders if and when he should transfer them to an LLC. 

If you’re thinking, "I love the Big Picture Retirement podcast!” please consider rating and reviewing this show! This helps us support more people -- just like you -- move toward a confident retirement. Just scroll down to the “ratings and reviews” section, tap to rate with five stars, and select “Write a Review.” Then be sure to let us know what you loved most about the episode!

Also, if you haven’t done so already, follow the podcast. We add new content every week, and if you’re not following, you’ll likely miss out. Follow now! 

Don’t miss the Big Picture Retirement Planning Cheat Sheet. We've distilled the essential brackets, thresholds, and rules of retirement into an easy-to-digest, three-page summary. 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://www.carrolladvisory.com/ 

Contact John’s team at https://www.rossandshoalmire.com/ 

Could 2025 be a stormy year for the stock market? In this episode, we explore five potential triggers that could send markets into turmoil. From the unpredictability of Trump-era “tape bombs” to a potential bursting of the AI bubble, we break down the risks investors should watch for. We also examine how protectionist trade policies, signs of an economic slowdown, and a possible Federal Reserve policy pivot could create turbulence. If you're looking to stay ahead of the curve and prepare for what’s next, this is the episode for you.

If you’re thinking, "I love the Big Picture Retirement podcast!” please consider rating and reviewing this show! This helps us support more people -- just like you -- move toward a confident retirement. Just scroll down to the “ratings and reviews” section, tap to rate with five stars, and select “Write a Review.” Then be sure to let us know what you loved most about the episode!

Also, if you haven’t done so already, follow the podcast. We add new content every week, and if you’re not following, you’ll likely miss out. Follow now! 

Don’t miss the Big Picture Retirement Planning Cheat Sheet. We've distilled the essential brackets, thresholds, and rules of retirement into an easy-to-digest, three-page summary. 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://www.carrolladvisory.com/ 

Contact John’s team at https://www.rossandshoalmire.com/ 

Today, we tackle a question from Patrick about the nuances of capital gains taxes on the sale of a primary residence. We break down how community property laws can impact your tax liability, the role of improvements in calculating your cost basis, and other key considerations to keep in mind when selling your home.

If you’re thinking, "I love the Big Picture Retirement podcast!” please consider rating and reviewing this show! This helps us support more people -- just like you -- move toward a confident retirement. Just scroll down to the “ratings and reviews” section, tap to rate with five stars, and select “Write a Review.” Then be sure to let us know what you loved most about the episode!

Also, if you haven’t done so already, follow the podcast. We add new content every week, and if you’re not following, you’ll likely miss out. Follow now! 

Don’t miss the Big Picture Retirement Planning Cheat Sheet. We've distilled the essential brackets, thresholds, and rules of retirement into an easy-to-digest, three-page summary. 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://www.carrolladvisory.com/ 

Contact John’s team at https://www.rossandshoalmire.com/ 

How could Trump’s tax policies impact your retirement plans? In this episode, we break down the potential changes, from tax cuts to shifting brackets, and discuss what they could mean for your savings, Social Security, and investment strategies. 

If you’re thinking, "I love the Big Picture Retirement podcast!” please consider rating and reviewing this show! This helps us support more people -- just like you -- move toward a confident retirement. Just scroll down to the “ratings and reviews” section, tap to rate with five stars, and select “Write a Review.” Then be sure to let us know what you loved most about the episode!

Also, if you haven’t done so already, follow the podcast. We add new content every week, and if you’re not following, you’ll likely miss out. Follow now! 

Don’t miss the Big Picture Retirement Planning Cheat Sheet. We've distilled the essential brackets, thresholds, and rules of retirement into an easy-to-digest, three-page summary. 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://www.carrolladvisory.com/ 

Contact John’s team at https://www.rossandshoalmire.com/ 

In this episode, we’re diving into the latest legal drama surrounding the Corporate Transparency Act (CTA). A federal judge in Texas has temporarily blocked this law, which would have required U.S. businesses to report detailed information about their stakeholders to the government. What does this mean for business owners? Is this a win for small businesses or just a delay in the inevitable? We'll break down the law, the court’s decision, and what might happen next—all in plain English. 

If you’re thinking, "I love the Big Picture Retirement podcast!” please consider rating and reviewing this show! This helps us support more people -- just like you -- move toward a confident retirement. Just scroll down to the “ratings and reviews” section, tap to rate with five stars, and select “Write a Review.” Then be sure to let us know what you loved most about the episode!

Also, if you haven’t done so already, follow the podcast. We add new content every week, and if you’re not following, you’ll likely miss out. Follow now! 

Don’t miss the Big Picture Retirement Planning Cheat Sheet. We've distilled the essential brackets, thresholds, and rules of retirement into an easy-to-digest, three-page summary. 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://www.carrolladvisory.com/ 

Contact John’s team at https://www.rossandshoalmire.com/ 

In this episode, we’re breaking down common myths about what a Will can actually take care of. A lot of people think a will covers everything, but it’s not that simple! We’ll explain how probate works, why some assets don’t go through your will, and what your will can’t control — like retirement accounts or jointly owned property. We’ll also talk about other tools you might need to make sure your plans really happen the way you want. Join us to learn what your will really does and avoid surprises for your family down the road.

If you’re thinking, "I love the Big Picture Retirement podcast!” please consider rating and reviewing this show! This helps us support more people -- just like you -- move toward a confident retirement. Just scroll down to the “ratings and reviews” section, tap to rate with five stars, and select “Write a Review.” Then be sure to let us know what you loved most about the episode!

Also, if you haven’t done so already, follow the podcast. We add new content every week, and if you’re not following, you’ll likely miss out. Follow now! 

Don’t miss the Big Picture Retirement Planning Cheat Sheet. We've distilled the essential brackets, thresholds, and rules of retirement into an easy-to-digest, three-page summary. 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://www.carrolladvisory.com/ 

Contact John’s team at https://www.rossandshoalmire.com/ 

In this episode, we break down simple strategies to protect your retirement savings when the market gets rough. We’ll start with why staying calm is key and how planning ahead can help you avoid emotional decisions. You'll learn how to match your investments with both your comfort level and your financial goals, plus why a balanced mix and a short-term “spending bucket” can keep you from selling at the wrong time. We’ll also cover how fees impact your savings and why it’s worth checking if they’re delivering good value. Finally, we’ll share the benefits of regularly reviewing your plan and how smart tax strategies can give you a boost during downturns.

If you’re thinking, "I love the Big Picture Retirement podcast!” please consider rating and reviewing this show! This helps us support more people -- just like you -- move toward a confident retirement. Just scroll down to the “ratings and reviews” section, tap to rate with five stars, and select “Write a Review.” Then be sure to let us know what you loved most about the episode!

Also, if you haven’t done so already, follow the podcast. We add new content every week, and if you’re not following, you’ll likely miss out. Follow now! 

Don’t miss the Big Picture Retirement Planning Cheat Sheet. We've distilled the essential brackets, thresholds, and rules of retirement into an easy-to-digest, three-page summary. 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://www.carrolladvisory.com/ 

Contact John’s team at https://www.rossandshoalmire.com/ 

Today we discuss the pros and cons of downsizing in retirement. We discuss how selling your home can reduce expenses, simplify your lifestyle, and free up money for travel or investments. But we also cover the potential downsides, like emotional attachment to your family home and the hidden costs of moving. Tune in to help decide if downsizing is the right move for you.

If you’re thinking, "I love the Big Picture Retirement podcast!” please consider rating and reviewing this show! This helps us support more people -- just like you -- move toward a confident retirement. Just scroll down to the “ratings and reviews” section, tap to rate with five stars, and select “Write a Review.” Then be sure to let us know what you loved most about the episode!

Also, if you haven’t done so already, follow the podcast. We add new content every week, and if you’re not following, you’ll likely miss out. Follow now! 

Don’t miss the Big Picture Retirement Planning Cheat Sheet. We've distilled the essential brackets, thresholds, and rules of retirement into an easy-to-digest, three-page summary. 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://www.carrolladvisory.com/ 

Contact John’s team at https://www.rossandshoalmire.com/ 

In this episode, we talk about an important part of retirement planning that many people overlook—figuring out how long you might live. We explain why using average life expectancy or guessing based on family history can be risky, and why it’s important to plan for a longer life. We also share tools that can help you estimate how long your savings need to last, whether you’re planning on your own or with a partner. Making a solid plan for how long you’ll need your money is key to a secure retirement.

Resources to use: 

Actuaries Longevity Illustrator (ALI) https://www.longevityillustrator.org/  

SSA Life Expectancy Calculator https://www.ssa.gov/oact/population/longevity.html  

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://www.carrolladvisory.com/ 

Contact John’s team at https://www.rossandshoalmire.com/ 

Long-term care is a reality that many retirees will face, but the question is—how will you pay for it? In this episode, we break down the three primary ways to cover long-term care expenses. We’ll walk you through the pros and cons of each option and explain why planning ahead is critical. Plus, we’ll introduce a tool that can help you estimate the actual costs of care in your area. Whether you’re planning for yourself or a loved one, this episode will give you the insights you need to make an informed decision about long-term care expenses.

If you’re thinking, "I love the Big Picture Retirement podcast!” please consider rating and reviewing this show! This helps us support more people -- just like you -- move toward a confident retirement. Just scroll down to the “ratings and reviews” section, tap to rate with five stars, and select “Write a Review.” Then be sure to let us know what you loved most about the episode!

Also, if you haven’t done so already, follow the podcast. We add new content every week, and if you’re not following, you’ll likely miss out. Follow now! 

Don’t miss the Big Picture Retirement Planning Cheat Sheet. We've distilled the essential brackets, thresholds, and rules of retirement into an easy-to-digest, three-page summary. 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://www.carrolladvisory.com/ 

Contact John’s team at https://www.rossandshoalmire.com/ 

In this episode, we take a closer look at Monte Carlo simulations—a tool used in retirement planning to estimate your chances of success. But are those percentages really reliable? Can an 85% or 90% success rate give you confidence in your retirement plan? We’ll explain how these simulations work, how different assumptions can lead to very different results, and why you shouldn’t just rely on past returns. 

If you’re thinking, "I love the Big Picture Retirement podcast!” please consider rating and reviewing this show! This helps us support more people -- just like you -- move toward a confident retirement. Just scroll down to the “ratings and reviews” section, tap to rate with five stars, and select “Write a Review.” Then be sure to let us know what you loved most about the episode!

Also, if you haven’t done so already, follow the podcast. We add new content every week, and if you’re not following, you’ll likely miss out. Follow now! 

Don’t miss the Big Picture Retirement Planning Cheat Sheet. We've distilled the essential brackets, thresholds, and rules of retirement into an easy-to-digest, three-page summary. 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://www.carrolladvisory.com/ 

Contact John’s team at https://www.rossandshoalmire.com/