Big Picture Retirement®

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, what it can't prevent, and why even the best planning can't account for everything. Although this show...

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

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, or financial advice, you can engage Devin or John through their individual firms.  📍Contact Devin's te...

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 practical look at where AI can help with estate planning, where it can fall short, and why understanding wh...

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 to protect yourself.  Use our free retirement stress test assessment tool  https://www.carrolladvisory.c...

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 show does not provide specific tax, legal, or financial advice, you can engage Devin or John through the...

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...

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...

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...

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...

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...

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    📍Contact John's team at https://www.rossandshoalmire.com/   If you're thinking, "I love the Big Pict...

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 team at https://www.rossandshoalmire.com/   If you're thinking, "I love the Big Picture Retirement po...

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-kno...

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 John's team at https://www.rossandshoalmire.com/   If you're thinking, "I love the Big Picture Retireme...

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 th...

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 tha...

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 epis...

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.  📍Contact Devin's team at https://carrolladvisor...

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 a...

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 s...

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, an...

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...

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 D...

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.  📍Co...