REPLAY | The Surprisingly Hardest Part of Retirement
Release Date: 03/03/2025
Inbox Question | How Much Umbrella Insurance Do You Need?
Big Picture Retirement®
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 📍Contact John’s team at If you’re...
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Inbox Question | How the Small Estate Affidavit Process Works
Big Picture Retirement®
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 📍Contact John’s team at...
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Listener Q&A: Trusts, IRMAA, Inheritance Taxes, Capital Gains, and More
Big Picture Retirement®
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...
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The 3 Parts to a Perfect Estate Plan – Part 3: Protecting the Beneficiaries’ Inheritance (Estate Planning Series Finale)
Big Picture Retirement®
In the final installment of our 3-part estate planning series, we dive into one of the most overlooked—but critically important—aspects of planning: protecting your heirs’ inheritance. It’s not enough to simply leave assets to your loved ones. Without proper planning, those assets could be exposed to divorce, lawsuits, creditors, or mismanagement. We’ll explore how using trusts can provide long-term protection and flexibility, and why leaving assets outright may be a costly mistake. You’ll learn how to: Safeguard inheritances from a beneficiary’s divorce or personal liabilities...
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Inbox Question | Home Equity for Long Term Care
Big Picture Retirement®
Today we answer Jeff’s question about using home equity to pay for end-of-life care — from tapping into equity for in-home support to selling the home to cover nursing home costs. In high-cost states like California, many seniors are house rich and cash poor, and this episode explores strategies to help families navigate that challenge. 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 📍Contact John’s team at If you’re thinking, "I love the...
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The 3 Parts to a Perfect Estate Plan – Part 2c: Common Mistakes & Oversights
Big Picture Retirement®
In this episode, we shine the light on common estate planning mistakes that can derail even the best intentions. We discuss the risks of failing to update beneficiary designations and why relying solely on joint ownership can create unexpected complications. 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 📍Contact John’s team at If you’re thinking, "I love the Big Picture Retirement podcast!” please consider rating and reviewing this show!...
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Inbox Question | Medicaid for Parents
Big Picture Retirement®
Today we answer a question from Cathy about helping aging parents in California navigate care costs, preserve limited resources, and explore options like pro bono legal support. 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 📍Contact John’s team at 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...
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The 3 Parts to a Perfect Estate Plan – Part 2b: Tax Considerations
Big Picture Retirement®
In this episode, we cover key tax considerations around wealth transfer. We cover the differences between federal estate tax and state inheritance tax, and explain why the stepped-up basis is such a powerful tool for minimizing capital gains taxes for heirs. 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 📍Contact John’s team at If you’re thinking, "I love the Big Picture Retirement podcast!” please consider rating and reviewing this show!...
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Inbox Question | Company Stock in 401K
Big Picture Retirement®
In this episode, Brian asks some great questions about using Net Unrealized Appreciation (NUA) for company stock inside a 401(k). We dive into the rules, timing, and strategies that could lead to major tax savings—if you do it right. We cover: What exactly is NUA and why it matters Can you use NUA before retirement? Do you need to be age 59½? Can you move the stock out in segments, or does it have to be all at once? Common mistakes that could cost you Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their...
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The 3 Parts to a Perfect Estate Plan: Part 2a: Non-Probate Transfers
Big Picture Retirement®
In this episode, we explore how to pass on your assets smoothly and efficiently—without dragging your loved ones through probate court. You’ll learn why probate can be costly and time-consuming, and how non-probate strategies like beneficiary designations, joint ownership, and revocable living trusts can help you keep more money in your family’s hands and less in legal fees. 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 📍Contact John’s team at...
info_outlineFor 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. With the right roadmap, retirees can grant themselves permission to spend, savoring the fruits of their labor with the confidence that their financial future remains secure. Join us as we share real-life stories of this struggle and offer insights into crafting a plan that truly brings 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!
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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.