Devin Carroll, CFP® & John Ross, JD
Big Picture Retirement®
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.
Author
Devin Carroll, CFP® & John Ross, JD
Category
Podcast website
Latest episode
Jun 15, 2026
Where to listen?
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Episodes
Inbox Questions | When Should You Stop Using TurboTax? 02.01.2025 12:40
Today, we tackle a question many retirees face: Can you manage your taxes with DIY software like TurboTax, or is it time to bring in a professional? We'll explore the challenges of navigating tax complexities in retirement, including 401(k) rollovers, RMDs, and other scenarios that could make filing trickier than expected. If you're thinking, "I love the Big Picture Retirement podcast!" please co...
Inbox Questions | When Should You Use An LLC? 20.12.2024 9:38
We answer a question from a 44-year-old Pittsburgh bus driver earning over six figures annually who maxes out a Roth IRA, contributes 10.5% to a 457 plan, and is covered by a pension. He owns five rental properties in his name and wonders if and when he should transfer them to an LLC. If you're thinking, "I love the Big Picture Retirement podcast!" please consider rating and reviewing this show!...
5 Reasons 2025 Could Be a Turbulent Year for Stocks 16.12.2024 32:22
Could 2025 be a stormy year for the stock market? In this episode, we explore five potential triggers that could send markets into turmoil. From the unpredictability of Trump-era "tape bombs" to a potential bursting of the AI bubble, we break down the risks investors should watch for. We also examine how protectionist trade policies, signs of an economic slowdown, and a possible Federal Reserve po...
Inbox Questions | Capital Gains on the Sale of Home 12.12.2024 7:02
Today, we tackle a question from Patrick about the nuances of capital gains taxes on the sale of a primary residence. We break down how community property laws can impact your tax liability, the role of improvements in calculating your cost basis, and other key considerations to keep in mind when selling your home. If you're thinking, "I love the Big Picture Retirement podcast!" please consider ra...
What Trump's Tax Policies Mean for Your Retirement 09.12.2024 32:04
How could Trump's tax policies impact your retirement plans? In this episode, we break down the potential changes, from tax cuts to shifting brackets, and discuss what they could mean for your savings, Social Security, and investment strategies. If you're thinking, "I love the Big Picture Retirement podcast!" please consider rating and reviewing this show! This helps us support more people -- jus...
BOI Reporting Delayed: The Future of the Corporate Transparency Act 05.12.2024 21:59
In this episode, we're diving into the latest legal drama surrounding the Corporate Transparency Act (CTA). A federal judge in Texas has temporarily blocked this law, which would have required U.S. businesses to report detailed information about their stakeholders to the government. What does this mean for business owners? Is this a win for small businesses or just a delay in the inevitable? We'll...
What Your Will WON'T Do 04.11.2024 45:54
In this episode, we're breaking down common myths about what a Will can actually take care of. A lot of people think a will covers everything, but it's not that simple! We'll explain how probate works, why some assets don't go through your will, and what your will can't control — like retirement accounts or jointly owned property. We'll also talk about other tools you might need to make sure your...
5 Ways to Make Your Retirement Recession-Ready 29.10.2024 30:32
In this episode, we break down simple strategies to protect your retirement savings when the market gets rough. We'll start with why staying calm is key and how planning ahead can help you avoid emotional decisions. You'll learn how to match your investments with both your comfort level and your financial goals, plus why a balanced mix and a short-term "spending bucket" can keep you from selling a...
Is Downsizing Right for Your Retirement? 21.10.2024 42:24
Today we discuss the pros and cons of downsizing in retirement. We discuss how selling your home can reduce expenses, simplify your lifestyle, and free up money for travel or investments. But we also cover the potential downsides, like emotional attachment to your family home and the hidden costs of moving. Tune in to help decide if downsizing is the right move for you. If you're thinking, "I love...
How Long Will I Live? Planning for Longevity in Retirement 14.10.2024 21:39
In this episode, we talk about an important part of retirement planning that many people overlook—figuring out how long you might live. We explain why using average life expectancy or guessing based on family history can be risky, and why it's important to plan for a longer life. We also share tools that can help you estimate how long your savings need to last, whether you're planning on your own...
3 Ways to Pay for Long-Term Care 07.10.2024 35:13
Long-term care is a reality that many retirees will face, but the question is—how will you pay for it? In this episode, we break down the three primary ways to cover long-term care expenses. We'll walk you through the pros and cons of each option and explain why planning ahead is critical. Plus, we'll introduce a tool that can help you estimate the actual costs of care in your area. Whether you're...
Monte Carlo Simulations: Is Your "Probability of Success" Trustworthy? 30.09.2024 38:27
In this episode, we take a closer look at Monte Carlo simulations—a tool used in retirement planning to estimate your chances of success. But are those percentages really reliable? Can an 85% or 90% success rate give you confidence in your retirement plan? We'll explain how these simulations work, how different assumptions can lead to very different results, and why you shouldn't just rely on past...
The Stock Market Gamble Most Investors Lose 23.09.2024 38:05
In this episode, we explore the realities of stock-picking, revealing that it's a gamble where the odds are heavily stacked against the average investor. Studies show that most individual stocks underperform or lose value over time, so we make a strong case for the smarter and more reliable approach. If you're thinking, "I love the Big Picture Retirement podcast!" please consider rating and revie...
How Kamala Harris's Housing Plan Could Drastically Change Wealth Transfer 16.09.2024 29:37
In this episode, we unpack Vice President Kamala Harris's ambitious plan to lower housing costs, which would be funded by adopting Senator Elizabeth Warren's sweeping estate tax overhaul. We explore the major changes proposed, including reducing the estate tax exclusion to $3.5 million, significantly increasing estate tax rates, and imposing new restrictions on popular estate planning tools like G...
Ed Slott Explains How to Outmaneuver the Tax Trap in Retirement 09.09.2024 35:59
Today we're joined by Ed Slott, the expert's expert on retirement planning, to talk about how to make the most of your retirement savings and avoid costly tax surprises. Ed explains why converting to Roth IRAs could be a smart move, the risks of sticking with traditional IRAs, and how to get ready for the taxes that come with required minimum distributions (RMDs). With Ed's advice, you'll learn ho...
Listener Voicemails: Super-funding 529s, Sophisticated Trusts, and Boosting Social Security Benefits 03.09.2024 46:04
In this episode, we're answering more listener voicemails about Social Security, gifting money, and estate planning. First, we help a listener who's trying to figure out the best way to maximize his wife's Social Security benefits. He's getting close to his full retirement age in 2025 and wants to make sure they get the most out of their benefits. Next, we talk about a question regarding "superfun...
Listener Q&A: Demystifying Brokerage Statements, Retirement Readiness, and Investment Strategies 26.08.2024 33:40
Today, Devin and Alexander are back answering listener questions. Tune in as we explore: Jamie's request for a detailed walkthrough of a monthly brokerage account statement, explaining where to find and understand fees, and demystifying various financial terms in plain English. Carl's situation as a 58-year-old with a diversified $1.1 million nest egg, seeking advice on overcoming the fear of reti...
Listener Voicemails: Social Security, Trusts, and IRA Math Mysteries 19.08.2024 35:17
In this episode we're answering listener voicemails and tackling some tough questions about Social Security, RMDs, estate planning, and more. First up, we help Diane, whose husband is a minister, figure out why his Social Security benefits don't include his housing allowance, even though he pays taxes on it. Then, we talk through a listener's concerns about how changing the title on a brokerage ac...
Listener Q&A: Navigating RMDs, Investment Strategies, and Retirement Income Planning 12.08.2024 38:53
In this episode of Big Picture Retirement, Devin is joined by Alexander Davis, a financial advisor at Carroll Advisory Group, to address some of the most pressing questions from our listeners. Together, they answer a range of questions, including: Charles' query on the order and process of completing Required Minimum Distributions (RMDs) before making Roth Conversions. Ted's strategy on transition...
Listener Q&A: Tax Strategies, Inheritances, Annuities, and More 05.08.2024 28:58
In this episode, Devin and John dive into a variety of listener questions, discussing annuities, maxing out retirement plans, why HSAs aren't widely talked about, IRMAA, and more. Tune in as we explore: Claudia's Situation: Understanding the distribution requirements for inherited qualified and unqualified MYGA accounts in light of recent tax law changes. We discuss the tax implications of cashing...
Listener Q&A: Navigating Taxes, Trusts, and More 29.07.2024 42:55
In this episode of Big Picture Retirement, we're back answering more of our listener-submitted questions. Join us as we cover: Anna's Query : When will NESARA begin? Ron's Question : Clarification on calculating taxes on Social Security benefits using our Cheat Sheet, specifically addressing whether AGI already includes SS benefits or if an additional 50% is added. Anne's Concerns : Discussing the...
Navigating Social Security: Listener Questions Answered 22.07.2024 35:51
In this episode of the Big Picture Retirement podcast, we dive into listener questions about Social Security, tackling a wide range of scenarios to help you navigate the complexities of your benefits. Lois asks about the earnings limit for survivor benefits versus other benefits for someone born in 1955. She's been told she must repay two months of benefits because her earnings exceeded the limit....
Listener Questions Answered: Reverse Mortgages, Healthcare Before Medicare, and More! 15.07.2024 44:28
In this episode, we tackle a diverse range of listener questions from reverse mortgages, annuities, Roth conversions, healthcare before the Medicare age, and a lot more. Tune in as we discuss: Al's Question: Recommendations for reverse mortgages and the conditions under which they can be beneficial. Paul's Inquiry: Using deferred annuities, specifically laddering Fixed Income Annuities with no fe...
Answering Listener Questions on Social Security 08.07.2024 40:22
In this episode, Devin dives deep into the Social Security questions sent in by our listeners. Topics include questions on the earnings limit, spousal benefits, survivor benefits, and the big one...how future benefit cuts could impact retirees 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 l...
The Power of Donor Advised Funds 10.06.2024 30:59
If you regularly donate to your church or other charities, donor advised funds (DAFs) might be something you want to look into. These funds offer some big perks. First off, you get a potential tax deduction in the year you contribute, even if the money is given out to charities gradually. Secondly, you have the freedom to decide when to donate. This means if you're facing a high tax bill one year,...
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