PODCAST · business
Big Picture Retirement®
by Devin Carroll, CFP® & John Ross, JD
Planning for, or already enjoying, your retirement? This is the show for you.The success of your retirement hinges on how well you connect the dots between legal, tax, and financial planning. Join your hosts John Ross, JD and Devin Carroll, CFP® as they dig beneath the surface to help you gain the confidence and clarity needed to navigate your retirement journey successfully.
Episodes
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Dolly Parton Had an Estate Plan. So What Went Wrong?
Dolly Parton had hundreds of millions of dollars, sophisticated estate planning, and a plan for what would happen after she was gone. Yet conflict still followed her death. In this episode, we look at what happened and the important lessons it offers about what a good estate plan can accomplish,...
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A Very Rare Opportunity for Retirees
Stocks are near record highs while fixed-income yields are at levels we haven't seen in nearly 20 years. That combination may give retirees an unusual opportunity—but taking advantage of it requires thinking differently about how a retirement portfolio should be built. Although this show does not...
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7 Social Security Rules Every Retiree Needs to Know
Smart retirees can still miss important Social Security rules. In this episode, we cover 7 common rules that even well-informed retirees often overlook, and how those blind spots can affect taxes, benefits, and the overall retirement plan. Although this show does not provide specific tax, legal…
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Can ChatGPT Write Your Will?
Can AI really help you create an estate plan, or could it create problems your family won't discover until it's too late? In this episode, we review a real Texas will and uncover several surprising issues involving beneficiary requirements, executor compensation, and a Lady Bird deed. It's a...
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Do Retirees Actually Run Out of Money?
Do retirees actually run out of money? After reading hundreds of real retirement stories from people who did, one pattern became clear: it usually wasn't poor investing that caused the problem. In this episode, we discuss the six most common reasons retirement plans fail and what you can do now…
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They Froze His $3,000,000 Retirement Account
Can your brokerage firm actually stop you from accessing your own money? In this episode, we walk through a real case involving a $3 million retirement account, explain when firms are allowed to place a temporary hold, and show you what you can do now to protect your independence. Although this...
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Will A Roth Conversion Save You Taxes?
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...
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The Gift Tax Loophole Congress Wants to Close
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...
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How to Get a Full Step-Up in Basis (Even If You Don't Live in a Community Property State)
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...
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The Social Security Earnings Limit May Be Eliminated
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...
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What 75 Year Old Retirees Regret Most
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...
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Inbox Question | Leveraged ETFs for Supercharging Retirement Savings
Kevin asks about using leveraged ETFs (2x and 3x return) for his retirement savings. LEverage 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...
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Inbox Question | QCD from a Workplace Retirement Plan
Ann asks about making qualified charitable distributions from her 457 plan. 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…
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You're Probably Looking at the Wrong Estate Tax
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...
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Inbox Question | Should I Use A Spendthrift Trust?
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. 📍Contact Devin's team at https://carrolladvisory.co/podcast1 📍Contact…
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How Your AI Data Could Be Used Against You
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...
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Should a Blood Test Shape Your Retirement Plan?
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...
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Why Recency Bias Is Dangerous for Today's Retirees
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...
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Five Retirement Loose Ends You Can't Ignore
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...
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Planning for Single Retirees — Part 4: Long-Term Care, Incapacity, and Estate Planning
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...
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Planning for Single Retirees — Part 3: Tax Planning and Roth Conversions
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…
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Planning for Single Retirees — Part 2: Social Security Claiming Decisions
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...
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Planning for Single Retirees — Part 1: Why Retirement Is Different When You're Solo
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,...
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7 Keys to a More Financially Stable 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...
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How to Buy or Sell a Business the Right Way
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...
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Inbox Question | Should Advisors Provide Client References
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...
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The Federal Income Tax: Coming to an End?
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...
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Inbox Question | Managing Allocation Across Many Accounts
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...
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Key Changes for 2026
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…
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5 Things Your Attorney Doesn't Want to Hear
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…
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Inbox Question | Roth Conversion Strategy for High Earners
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…
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Is This the Worst Time to Retire? 3 Ways to Prepare (Just in Case)
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...
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Inbox Question | Typical Costs of Estate Planning
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...
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The Hidden Cost of Delaying Social Security
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...
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Inbox Question | What's the Big Deal with HSAs
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...
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Inbox Question | Using IRA Withdrawals to Fund Daughter's Roth
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...
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The Great Retirement Plan Illusion
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...
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The Hidden Estate Tax Lesson in the $1.8 Billion Powerball
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...
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Why So Many Americans Are Claiming Social Security Early in 2025
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…
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Three Priorities That Should Shape Your Social Security Decision
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…
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What Millionaire Retirees Fear Most (But Rarely Talk About)
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...
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Private Equity Meets Your 401(k)
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...
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5 Mistake Most Millionaire Retirees Make
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...
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Overview of the One, Big, Beautiful Bill
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....
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Inbox Question | How Filing Early Impacts the Spousal Benefit
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…
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Why Taxes In Retirement Get More Complicated
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…
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Inbox Question | The Good Life Abroad: Would We Go?
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…
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Inbox Question | How Much Umbrella Insurance Do You Need?
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…
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Inbox Question | How the Small Estate Affidavit Process Works
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...
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Listener Q&A: Trusts, IRMAA, Inheritance Taxes, Capital Gains, and More
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…
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ABOUT THIS SHOW
Planning for, or already enjoying, your retirement? This is the show for you.The success of your retirement hinges on how well you connect the dots between legal, tax, and financial planning. Join your hosts John Ross, JD and Devin Carroll, CFP® as they dig beneath the surface to help you gain the confidence and clarity needed to navigate your retirement journey successfully.
HOSTED BY
Devin Carroll, CFP® & John Ross, JD
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Frequently Asked Questions
How many episodes does Big Picture Retirement® have?
Big Picture Retirement® currently has 313 episodes available on PodParley. New episodes are automatically indexed when they're published to the podcast feed.
What is Big Picture Retirement® about?
Planning for, or already enjoying, your retirement? This is the show for you.The success of your retirement hinges on how well you connect the dots between legal, tax, and financial planning. Join your hosts John Ross, JD and Devin Carroll, CFP® as they dig beneath the surface to help you gain the...
How often does Big Picture Retirement® release new episodes?
Big Picture Retirement® publishes regularly with 313 episodes available. Check the episode list for the typical release schedule.
Where can I listen to Big Picture Retirement®?
You can listen to Big Picture Retirement® on PodParley by clicking any episode. We provide an embedded audio player for direct listening, and you can also subscribe via your preferred podcast app using the RSS feed.
Who hosts Big Picture Retirement®?
Big Picture Retirement® is created and hosted by Devin Carroll, CFP® & John Ross, JD.
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