Episodes

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. 📍Contact Devin’s team at https://carrolladvisory.co/podcast1 📍Contact John’s team at https://www.rossandshoalmire.com/ If you’re thinking, "I l...

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 marke...

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. 📍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! T...

You’ve heard it a thousand times: “Wait until 70 to file for Social Security.” But if that’s such obvious advice, why do most retirees file earlier? In this episode, we uncover the hidden cost of waiting and the trade-offs most experts ignore. You’ll learn how early withdrawals, taxes, and real-life emotions all change the math—and why the “right” answer isn’t the same for everyone. Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John throug...

Daryl wants a simple explanation of why Health Savings Accounts matter and what makes them such a powerful retirement planning tool. 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 thi...

John asks if taking larger IRA withdrawals beyond his RMD to fund his daughter’s Roth IRA makes sense as a strategy to reduce future RMDs, lower estate taxes, and pass on tax-free assets. 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 Retire...

Many retirees think they have a plan when what they really have is an investment pitch dressed up as planning. This episode uncovers why that illusion is dangerous, the costly mistakes it hides, and how to spot the difference between true planning and portfolio sales. 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 http...

Winning the lottery may be rare, but estate tax mistakes aren’t. In this episode, we use the recent $1.8 billion Powerball jackpot to highlight how generational wealth can be eroded by estate taxes and how tools like a BDIT can help protect growth assets. We’ll also show why this strategy isn’t just for lottery winners, but for anyone holding assets with explosive growth potential. Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through...

So far in 2025, early Social Security filings have jumped dramatically compared to last year. Nearly half of those filing early say they’re doing so because they’re worried about cuts. But will filing early really help? In this episode, we talk about what the data shows, what most people get wrong about Social Security cuts, and how to think about your filing strategy with clarity, not fear. Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or Jo...

When should you claim Social Security? For high-net-worth retirees, this is not a simple decision. In this episode, we explain why Social Security is not just a monthly check but a strategic part of a well-built retirement plan. Devin begins by challenging the common belief that wealthy retirees do not need to think about Social Security. In reality, those with more assets often have more choices, and those choices make the timing decision even more important. You will learn about the three co...

For many affluent retirees, the biggest financial fear isn’t market volatility or rising taxes. It’s this simple question: What happens if I’m not the one here to manage the plan? In this episode, we talk about a deeply personal concern shared by countless couples. When one spouse manages the investment strategy, the tax planning, and the long-term vision, the other is often left trusting that everything will work out. That trust may work fine today, but what if something changes tomorrow? What...

Should everyday investors be allowed to hold private equity, venture capital, or even crypto in their 401(k)s? A new executive order suggests it might soon be possible. In this episode, we walk through the real implications of this move, especially for retirement savers who may not be equipped to handle the risks. We start with a quick quiz that highlights a troubling truth: most 401(k)-only investors don’t understand basic financial principles like compound interest, inflation, or diversificat...

You’ve done the hard work. You saved consistently, built a seven-figure portfolio, and are ready to enjoy retirement. But even millionaire retirees can make mistakes that put their plans at risk. In this episode, Devin shares the five most common retirement mistakes he sees among high-net-worth clients. These include missing long-term tax planning opportunities, underestimating healthcare and long-term care costs, failing to plan for success as well as failure, approaching income withdrawals wit...

In this episode, we break down the newly signed One Big Beautiful Bill Act (OBBBA) and what it means for retirees. From the extension of the 2017 tax cuts to new rules around Roth conversions, Social Security taxation, and a brand-new "Senior Deduction"—there’s a lot packed into this legislation. We’ll walk you through the major provisions, highlight how they may affect your retirement income strategy, and share practical planning moves to consider. Although this show does not provide specific ...

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. 📍Contact De...

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 fi...

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. 📍Contact Devin’s team at https://carrolladvisory.co/podcast1 📍Contact John’s team at https://www.rossandshoa...

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. 📍Conta...

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 ind...

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 no...

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 lear...

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 tea...

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 https://carrolladvisory.co/podcast1 📍Contact John’s team at https://www....

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...