Three Priorities That Should Shape Your Social Security Decision
Release Date: 09/01/2025
How to Buy or Sell a Business the Right Way
Big Picture Retirement®
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. 📍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...
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Inbox Question | Should Advisors Provide Client References
Big Picture Retirement®
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 📍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...
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The Federal Income Tax: Coming to an End?
Big Picture Retirement®
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 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...
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Inbox Question | Managing Allocation Across Many Accounts
Big Picture Retirement®
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 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...
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Key Changes for 2026
Big Picture Retirement®
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 Security earnings test thresholds. We also walk through the shifting rules around capital gains, the standard deduction, and the return of the SALT cap. For charitable giving, we outline the new above the line deduction, the AGI floor for itemizing, the cap tied to the highest tax rate, and the updated QCD...
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5 Things Your Attorney Doesn’t Want to Hear
Big Picture Retirement®
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, and realistic expectations. If you want to make better decisions and create an estate plan your family can actually rely on, this episode will point you in the right direction. Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their...
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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...
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Big Picture Retirement®
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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...
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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_outlineWhen 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 guaranteed income, and coordinating Social Security with the rest of your retirement plan. Devin explains how each of these goals can shape your filing strategy and why getting the timing right can support better outcomes for both income and taxes.
This episode also covers how delaying benefits can increase lifetime income for a surviving spouse, reduce tax burdens through coordinated withdrawals, and help create a stronger income floor that is not tied to the markets.
If you have flexibility in when you file, use it wisely. Social Security decisions should support your long-term goals, reflect your income needs, and fit within your overall tax and investment strategy.
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!
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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
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