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.