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PODCAST

Big Picture Retirement®

Devin Carroll, CFP® & John Ross, JD

Planning for, or already enjoying, your retirement? This is the show for you. The success of your retirement hinges on how well you connect the dots between legal, tax, and financial planning. Join your hosts John Ross, JD and Devin Carroll, CFP® as they dig beneath the surface to help you gain the confidence and clarity needed to navigate your retirement journey successfully.

business investing

All Episodes

36:54

Why Recency Bias Is Dangerous for Today's Retirees

Big Picture Retirement® ·

2026/03/09

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

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29:31

Five Retirement Loose Ends You Can't Ignore

Big Picture Retirement® ·

2026/02/16

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

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01:10:04

Planning for Single Retirees — Part 4: Long-Term...

Big Picture Retirement® ·

2026/02/09

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

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32:34

Planning for Single Retirees — Part 3: Tax Planning...

Big Picture Retirement® ·

2026/02/02

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

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33:59

Planning for Single Retirees — Part 2: Social...

Big Picture Retirement® ·

2026/01/26

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

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31:53

Planning for Single Retirees — Part 1: Why Retirement...

Big Picture Retirement® ·

2026/01/19

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,

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36:16

7 Keys to a More Financially Stable Retirement

Big Picture Retirement® ·

2026/01/05

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

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47:52

How to Buy or Sell a Business the Right Way

Big Picture Retirement® ·

2025/12/15

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

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12:36

Inbox Question | Should Advisors Provide Client...

Big Picture Retirement® ·

2025/12/11

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

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31:19

The Federal Income Tax: Coming to an End?

Big Picture Retirement® ·

2025/12/08

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

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09:04

Inbox Question | Managing Allocation Across Many...

Big Picture Retirement® ·

2025/12/04

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

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36:13

Key Changes for 2026

Big Picture Retirement® ·

2025/12/01

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

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34:01

5 Things Your Attorney Doesn't Want to Hear

Big Picture Retirement® ·

2025/11/24

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

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08:30

Inbox Question | Roth Conversion Strategy for High...

Big Picture Retirement® ·

2025/11/13

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

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31:11

Is This the Worst Time to Retire? 3 Ways to Prepare...

Big Picture Retirement® ·

2025/11/10

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

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09:22

Inbox Question | Typical Costs of Estate Planning

Big Picture Retirement® ·

2025/11/06

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

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33:22

The Hidden Cost of Delaying Social Security

Big Picture Retirement® ·

2025/11/03

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

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08:13

Inbox Question | What's the Big Deal with HSAs

Big Picture Retirement® ·

2025/10/30

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

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07:08

Inbox Question | Using IRA Withdrawals to Fund...

Big Picture Retirement® ·

2025/10/16

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

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26:14

The Great Retirement Plan Illusion

Big Picture Retirement® ·

2025/10/06

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

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99 results

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