Planning for Single Retirees — Part 4: Long-Term Care, Incapacity, and Estate Planning
Release Date: 02/09/2026
Planning for Single Retirees — Part 4: Long-Term Care, Incapacity, and Estate Planning
Big Picture Retirement®
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 accounts and professional care managers can step in when needed. They also cover how...
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Planning for Single Retirees — Part 3: Tax Planning and Roth Conversions
Big Picture Retirement®
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 Medicare premiums factor into tax decisions, and why time horizon matters more when there’s...
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Planning for Single Retirees — Part 2: Social Security Claiming Decisions
Big Picture Retirement®
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 emotional side of these decisions—fear of running out of money, fear of dying too...
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Planning for Single Retirees — Part 1: Why Retirement Is Different When You’re Solo
Big Picture Retirement®
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, long-term care, and estate planning. This episode isn’t about tactics. It’s about...
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7 Keys to a More Financially Stable Retirement
Big Picture Retirement®
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 📍Contact John’s team at If you’re thinking, "I love the Big Picture Retirement podcast!”...
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How to Buy or Sell a Business the Right Way
Big Picture Retirement®
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 📍Contact John’s team at If you’re thinking, "I love the Big Picture Retirement podcast!” please consider rating and reviewing this...
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Inbox Question | Should Advisors Provide Client References
Big Picture Retirement®
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 📍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 retirement. Just scroll down to the “ratings and...
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The Federal Income Tax: Coming to an End?
Big Picture Retirement®
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 📍Contact John’s team at If you’re thinking, "I love the Big Picture Retirement podcast!” please consider rating and reviewing this...
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Inbox Question | Managing Allocation Across Many Accounts
Big Picture Retirement®
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 📍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 retirement. Just scroll down to the...
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Key Changes for 2026
Big Picture Retirement®
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 deduction, the AGI floor for itemizing, the cap tied to the highest tax rate, and the updated QCD...
info_outlineIn 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 accounts and professional care managers can step in when needed. They also cover how isolation increases the risk of scams and exploitation, why consolidating accounts and simplifying your finances matters more as you age, and the estate planning details single retirees should get right now—from probate choices to charitable bequests and protections against bad actors.
If you’re single, widowed, divorced, or simply planning without a spouse you can rely on, this episode is about protecting your independence, your dignity, and your plan—before a crisis forces decisions for you.
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.