Big Picture Retirement

Today we answer a question from Ken, a recent retiree at 63, about how his Social Security claiming decision impacts his wife’s future spousal benefit. We break down how spousal benefits are calculated, whether the FRA (Full Retirement Age) amount is frozen when you claim early, and how COLA (Cost of Living Adjustments) factor into the equation. Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their individual firms. 

Most retirees think tax planning ends with knowing their tax bracket, but that’s just the beginning. In this episode, we unpack how different income sources interact in retirement, and how seemingly smart decisions can trigger hidden taxes, Medicare surcharges, and other costly surprises. Learn how to avoid the traps and make your retirement income work smarter. Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their individual firms. 

Today we answer a question from Chris about The Good Life Abroad and whether we plan to take a trip with the company. We share our thoughts on the concept, what interests us about their offerings, and whether a future review might be on the horizon. Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their individual firms. 

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. 

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. 

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 after the sale of a property? What about the "2 out of 5 years" exemption? Paying Inheritance Taxes – If all your accounts list beneficiaries, how will state inheritance taxes (like Pennsylvania's) get paid on time? Step-Up in Basis with TOD Deeds – In Oklahoma, does property with a Transfer on Death deed still receive a step-up in basis? Impact of Home Sale on IRMAA and Roth Conversions – How does selling a vacation home affec

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 Provide for special needs or disabled heirs without jeopardizing government benefits Handle contingency planning, including what happens if a beneficiary predeceases you Protect minor children using trusts instead of relying on court-supervised guardianships We also highlight common mistakes—like failing to update your estate plan after major life events—and share practical steps to avoid them. Although this show does not pro

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. 

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. 

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. 

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. 

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 individual firms. 

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. 

In this inbox episode, we break down how the Social Security earnings limit works—especially for C corp owners who split income between salary and dividends. Learn what counts toward the limit, what doesn’t, and how smart income structuring can help you avoid benefit reductions. Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their individual firms. 

In the first part of our series on estate planning, we laid the groundwork for why incapacity planning matters and what documents you need to get started. But there’s more to it than just having your paperwork in order. In this second episode on planning for incapacity, we take the conversation further by focusing on what happens when long-term care is needed. We’ll walk through the different types of care—home care, assisted living, and nursing homes—and how to plan ahead financially using private pay, long-term care insurance, or Medicaid planning. We’ll also highlight common pitfalls like outdated or missing Powers of Attorney, and the risks of DIY estate planning that can create real problems down the road. If you haven’t reviewed your incapacity planning documents lately—or if you’ve never had them in place—this episode is your call to action. Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their individual firms. 

Today kicks off a brand-new series on estate planning. Estate planning is one of those things everyone knows they should do—but far too many people put it off, sometimes until it’s too late. And the truth is, whether your financial situation is complex or pretty straightforward, having a solid estate plan isn’t just about what happens after you're gone. It’s also about making things easier for your loved ones—and protecting yourself—while you're still here. That’s why we’re launching this special series to break estate planning down into simple, practical steps. We’ll walk through the essential documents you need, the common mistakes that can derail a plan, and some of the more advanced strategies for protecting and passing on your wealth efficiently. Whether you’re starting from scratch or just need to update an existing plan, this series will give you the roadmap you need. Now, we originally thought we could cover the first part of this in a single episode—but planning for incapacity turned out to be too im

John asks about buying the individual sectors of the S&P 500 and rebalancing based on performance instead of simply buying an index fund. Devin shares the pros and cons that he can see with this strategy and shares what he thinks is a better approach.  Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their individual firms. 

Rosemary’s husband is scaling back to 32 hours a week as part of his transition plan before switching careers. With Social Security in mind, she asks: Will this reduced income impact their future benefits? In this episode, we break down how Social Security calculates benefits, whether lower earnings in the final working years can reduce your check, and what to consider before making the shift. If you’re thinking about adjusting your workload before retirement, this is an episode you won’t want to miss! Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their individual firms. 

Planning to travel in retirement? In this episode, I sit down with Andrew Motiwalla from The Good Life Abroad to discuss how retirees can make the most of their travel experiences—without the stress. We talk about: ✅ Why travel is at the top of most retirees' bucket lists ✅ How to plan trips that align with your passions ✅ The best underrated destinations for immersive experiences ✅ How to avoid common travel planning pitfalls ✅ How long-term travel is changing the way retirees experience the world If you’re looking to travel smarter, go beyond tourist hotspots, and make the most of your retirement years, this conversation is for you!

This week, we’re diving into a question about the tax treatment of Special Needs Trusts. There are two types—First-Party and Third-Party trusts—but how does each one affect taxes? We’ll break down key differences in taxation, who reports the income, and what trustees need to consider when filing returns. If you or a loved one rely on a Special Needs Trust, understanding the tax implications is essential. Tune in for a clear and practical breakdown! Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their individual firms.