Big Picture Retirement

Unless you're listening to this while flying in your own Gulfstream, federal estate taxes probably aren't something you need to worry about. In 2026, they only apply to estates over $15 million, or $30 million for married couples, so they impact a very small percentage of people. But state-level estate and inheritance taxes are a different story. In this episode, we break down how these lesser-known taxes work, which states still impose them, and why they can catch even well-prepared retirees off guard. While many states have eliminated these taxes to keep retirees from leaving, 12 states plus Washington, D.C. still have estate taxes, and five have inheritance taxes. Maryland is the only state that has both. If your goal is to pass on wealth efficiently, where you live could matter more than you think. Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their individual firms. 

A listener asks about a spendthrift trust for his adult "airhead" granddaughter.  Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their individual firms. 

More people are using AI tools every day to ask questions, solve problems, and even talk through personal decisions. But many users make one dangerous assumption: that their conversations are completely private. In reality, AI systems collect and process data in ways most people don't fully understand. That information could potentially be stored, analyzed, or used in ways you didn't intend. In this episode, we discuss how AI platforms handle user data, why you should be careful about what you share, and the simple mindset shift everyone should adopt when using AI tools. Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their individual firms. 

Advances in predictive medicine are starting to raise a fascinating question: what if we could estimate our longevity with much greater accuracy? New blood tests and biomarkers are being developed that may help identify risks for diseases years—or even decades—before symptoms appear. Some researchers believe these tools could eventually provide meaningful clues about how long we might live. If that happens, it could have major implications for retirement planning. Should information about your potential lifespan influence when you retire, how much you spend, or how you invest? In this episode, we explore how predictive medicine is evolving, what scientists are learning from advanced blood testing, and whether this kind of information could one day reshape how people plan for retirement. Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their individual firms. 

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 wrong risks at the wrong time, and how to build a retirement plan that works even when the future looks very different from the past. Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their individual firms. 

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. 

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 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 dig

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 only one lifetime to plan around. This episode isn't about squeezing out every last tax advantage. It's about protecting flexibility, avoiding irreversible mistakes, and building a plan that works without a backup. Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their individual firms. 

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 early, and the pressure of making irreversible choices alone. This episode isn't about finding the "perfect" strategy. It's about building a plan you can stick with, even when markets and assumptions don't cooperate. Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their individual firms. 

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 mindset. When you're planning alone, the goal isn't perfection. It's resilience. In Part 2, we begin with Social Security, the foundation for many single retirees. Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their individual firms. 

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. 

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. 

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. 

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. 

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. 

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 limit of one hundred eleven thousand dollars. If you want to understand how the 2026 landscape could affect your plan, this episode gives you the practical guidance you need. Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their individual firms. 

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 provide specific tax, legal, or financial advice, you can engage Devin or John through their individual firms. 

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. 

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. It's about preparation 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. 

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.