Devin Carroll, CFP® & John Ross, JD

Big Picture Retirement®

Business EN ↓ 307 episodes

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.

Author

Devin Carroll, CFP® & John Ross, JD

Category

Business

Latest episode

Jun 15, 2026

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Episodes

The Surprisingly Hardest Part of Retirement 30.10.2023

For countless retirees, the greatest challenge isn't saving money, but spending it. After years of diligent saving, the transition to drawing down those hard-earned funds can be fraught with anxiety and uncertainty. But what if there was a way to ease this tension? In this episode, we explore the often unexpected emotional hurdles of retirement spending and reveal the antidote: a well-defined plan...

Social Security In Digital Dollars Only?!? 16.10.2023

In this episode, we open the phone lines and talk directly with our listeners to answer their burning questions. Suzanne's Dilemma -  Suzanne from California is on the brink of retirement and finds herself at a crossroads regarding her Social Security collection and marriage. With a mix of emotions, financial goals, and intricate social security rules, we navigated her through her options and pote...

Straight From Our Inbox: Listener Voicemails and more 09.10.2023

In today's episode, Devin and John answer a few questions from listener's voicemails! Join us as we dissect these questions, providing you with actionable insights and strategies to give you clarity and confidence about your retirement. 🎙️📈👥 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 lik...

Is Your Advisor Worth 1%? 02.10.2023

In this episode, we dive into the real worth of a financial advisor. If they're only offering investment management or just lightly touching upon financial planning, is that 1% fee justifiable? Then Devin and John talk about the evolution of how compensation for advice has changed – from its commission-based roots to percentage-based asset management fees, and now, towards the emerging trend of fl...

LLC Protection: Myths, Realities, and Navigating Personal Judgments 25.09.2023

In this episode, John dives deep into the intricacies of charging orders for LLCs. If you own an LLC, what happens when there's a personal judgment against you? How do state laws influence the level of protection? Many view LLCs as a protective measure, especially when holding valuable assets like real estate. Yet, while these structures are designed to offer a shield, are there circumstances wher...

On Air - Your Software Is Getting It WRONG 21.09.2023

In this episode, we open the phone lines and talk directly with our listeners to answer their burning questions.   Mark from Maryland starts us off, delving into the graduated progression of taxation. Devin sheds light on the historical backdrop and the ongoing challenges of the Social Security Trust Fund, underscoring the reverberations of past political decisions. Lola from Kansas grapples with...

Will Roth IRAs Become Taxable? 18.09.2023

Is it possible that Roth IRAs will be taxable in the future?  Could they change the rules and start including the distributions from a Roth as part of your taxable income?  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 "r...

Has the IRS Ended the Step-Up Basis for Trusts? 11.09.2023

In this episode, we dive into the recent IRS revenue ruling that has the financial and estate planning communities buzzing. The possibility that trust accounts may no longer benefit from a step-up in basis has caused some panic among individuals who have used trust planning as the cornerstone of their estate plans. For decades, the step-up in basis has been a cornerstone of estate planning, allowi...

Straight From Our Inbox: Listener Voicemails on Social Security and More 05.09.2023

In today's episode, Devin and John answer a few questions from listener's voicemails. Here's a glimpse of what we discuss: Carol wonders if her husband can start collecting Social Security on her benefits, despite her already receiving hers. Cynthia brings a multifaceted query on government pensions, deceased spouse benefits, and the intricacies surrounding her mother's and stepfather's financial...

Most Common Filing Age, Roth Conversions, and More 14.08.2023

 In today's episode, Devin answers some of the most common questions he receives. What's the most common age to file for Social Security? Social Security Income Limit: Single or Joint Income? Full Retirement Age Increasing to 70? Spousal Benefits Calculation Can I undo a Roth Conversion? If you're thinking "I love the Big Picture Retirement podcast" please consider rating and reviewing this show!...

Should You Loan Money to Friends and Family?! 31.07.2023

Loaning money to family and friends can be seen as a generous act when they're caught in a financial crunch. However, such acts often come with a caveat - they tend to ruin relationships. If you're diligent about saving money, it's probable that your friends and family members will be aware of this fact, even if your lifestyle isn't extravagant. Consequently, you may find yourself being viewed as...

Retirement Reality Check: Should YOU Be Worried? 17.07.2023

Description: In this episode we dive into a recent eye-opening report from the Center for Retirement Research. The data reveals a surprising disconnect: while a significant number of pre-retirees remain nonchalant about their retirement, their current savings are far from adequate to support their post-retirement lifestyle. As anxiety and fear disorders are soaring to all-time highs, it's perplexi...

Unmasking the IUL Sales Pitch with Andy Panko 10.07.2023

In this episode we tackle the topic of Indexed Universal Life Insurance (IUL), a product often peddled by salespeople as the ultimate retirement solution. However, is all as it seems? We're delighted to welcome guest expert Andy Panko of Tenon Financial and host of the Retirement Planning Education podcast. Together, we dissect the IUL strategy, shedding light on the hidden truths and outright fal...

What is a Female? Why Definitions Matter In Estate Planning 03.07.2023

In the world of estate planning, words hold immense power. Does your estate plan have a definitions page that clearly defines the key terms? If not, there could be massive issues 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...

The 5 Surprise Retirement Expenses 19.06.2023

Retirement is often seen as a time of financial stability, but for many people, it can come with several surprises. Here are five retirement surprises you should be aware of, along with examples of how they can impact your retirement strategy. If you're thinking "I love the Big Picture Retirement podcast" please consider rating and reviewing this show! This helps me support more people -- just lik...

Inheritance Missteps: Navigating Trusts and Children 12.06.2023

In this episode, John and Devin dive into some of the nuances of inheritance planning, particularly when it comes to setting up trusts for children. As is the case with most important things, there are lots of hidden "gotchas" that can have unintended consequences. If you're thinking "I love the Big Picture Retirement podcast" please consider rating and reviewing this show! This helps me support m...

Lessons Learned from a Heart Attack 05.06.2023

Devin shares a personal story of how technology and a professional's inability to interpret the output of that technology led to financial and psychological consequences. The experience was as eye-opening as it was terrifying and taught Devin a valuable lesson about the importance of second opinions and the limitations of relying solely on technology or established routines. Devin's story doesn't...

4 Things Singles Should Know About Filing for Social Security 31.05.2023

Navigating the Social Security filing process as a single individual can be a daunting task. The considerations you need to make differ from those of married couples. In this episode, we aim to simplify this process and provide you with the essential information you need before filing for Social Security. Reasources mentioned in this episode: SSI Blog: Survivors' Benefits: Exceptions to the Marria...

Direct Indexing: Revolutionizing Investment Strategies or Just Hype? 23.05.2023

In this week's episode of the Big Picture Retirement podcast, we dive deep into the world of Direct Indexing. As a fairly new approach in the investment ecosystem, it promises tailored portfolio customization and potentential tax optimization. But are these benefits worth the potential pitfalls and complexities? Today Devin is joined by Alec and Alexander, two members of the advisory staff at Carr...

The Optimal Retirement Withdrawal Strategy 15.05.2023

The sequence that you use to withdraw your money in retirement can make a massive difference in the amount of taxes you pay AND how long your money lasts. In today's episode, we're talking about an alternate way to think about taking withdrawals that very few people are talking about. If you're thinking about retiring, or you've just retired, you're going to be glad you listened to this episode. I...

3 Reasons for Roth Conversions 08.05.2023

Roth conversions have become a trending topic, and for good reason. After paying taxes throughout one's life, it's desirable to strategically reduce taxes during retirement, if feasible. Nevertheless, the viability of a Roth conversion depends on individual circumstances, and after reviewing hundreds of Roth conversion plans, we've observed three primary reasons why a Roth conversion may be benefi...

How Divorce Attorneys Miss the Big Picture 01.05.2023

While divorce may mark the end of a marriage, it is also a critical juncture in a person's financial and estate planning, as it can significantly impact their future wealth, retirement, and inheritance. In this context, divorce attorneys who fail to consider the bigger picture of estate and financial planning may unwittingly leave their clients vulnerable to financial pitfalls and missed opportuni...

The 5 Phases of Saving for Retirement 24.04.2023

Saving for retirement is a lifelong process that unfolds through various stages. While the steps may differ based on individual circumstances, a general framework can be outlined. Each stage requires a different approach to ensure a secure and comfortable retirement. If you're thinking "I love the Big Picture Retirement podcast" please consider rating and reviewing this show! This helps me support...

Reverse Mortgages- Understanding the Pros and Cons 03.04.2023

"Is a reverse mortgage a good idea? It could be but there are certainly some pros and cons to think about before signing those papers. In today's episode, we break down what you should know." If you're thinking "I love the Big Picture Retirement podcast" please consider rating and reviewing this show! This helps me support more people -- just like you -- move toward a confident retirement. Just sc...

The Retirement Tax Torpedo 27.03.2023

The calculation the IRS uses to determine how you pay taxes on retirement income creates a danger zone where taxes can be SIGNIFICANTLY amplified. If you fall into this danger zone, you could pay a MUCH higher tax rate on your retirement income. 

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