Is This the Worst Time to Retire? 3 Ways to Prepare (Just in Case)
Release Date: 11/10/2025
Inbox Question | Roth Conversion Strategy for High Earners
Big Picture Retirement®
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 📍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...
info_outline
Is This the Worst Time to Retire? 3 Ways to Prepare (Just in Case)
Big Picture Retirement®
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...
info_outline
Inbox Question | Typical Costs of Estate Planning
Big Picture Retirement®
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 📍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...
info_outline
The Hidden Cost of Delaying Social Security
Big Picture Retirement®
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 through their individual firms. 📍Contact Devin’s team at ...
info_outline
Inbox Question | What’s the Big Deal with HSAs
Big Picture Retirement®
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 📍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...
info_outline
Inbox Question | Using IRA Withdrawals to Fund Daughter’s Roth
Big Picture Retirement®
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 📍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...
info_outline
The Great Retirement Plan Illusion
Big Picture Retirement®
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 📍Contact John’s team at If you’re thinking, "I love the Big Picture Retirement podcast!” please consider rating and reviewing...
info_outline
The Hidden Estate Tax Lesson in the $1.8 Billion Powerball
Big Picture Retirement®
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 their individual firms. 📍Contact Devin’s team at 📍Contact John’s...
info_outline
Why So Many Americans Are Claiming Social Security Early in 2025
Big Picture Retirement®
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 John through their individual firms. 📍Contact Devin’s team at ...
info_outline
Three Priorities That Should Shape Your Social Security Decision
Big Picture Retirement®
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 core priorities that should guide how and when you file: protecting a surviving spouse, maximizing...
info_outlineEveryone’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.
📍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.