Retirement planning with tax, legal, and financial context.
Big Picture Retirement® is a practical retirement-planning show built around listener questions and planning scenarios. Devin and John Ross move between tax rules, legal structures, financial tradeoffs, and side conversations with an easy, conversational rhythm.
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Big Picture Retirement® approaches retirement planning as a web of decisions that touch taxes, law, investments, family, health, and personal behavior. The show is conversational, but the subject matter is concrete. Devin and John Ross often begin with a listener question or a recent article, then use it as a doorway into a broader planning issue. A question about making a qualified charitable distribution from a workplace 457 plan becomes a lesson in the difference between an IRA, a deemed IRA, and a retirement plan that merely feels IRA-like. That kind of distinction is the show’s natural territory. It likes the fine print. It also likes plain English. Episodes move comfortably from estate taxes to spendthrift trusts, from Roth conversion timelines to business-sale structures, and from AI privacy concerns to the uncomfortable planning implications of predictive medical data. The tone is measured and practical, with enough humor to keep the material human. A tangent about pollen, the Villages, public speaking, Skid Row, or obsolete radio branding may sit beside a discussion of depreciation recapture or capital gains treatment. Those detours are part of the texture, not the destination. The show keeps returning to how decisions actually play out over time. It questions finish-line-only planning, simple withdrawal rules, blind cash hoarding, and assumptions that new tools or new information automatically make better choices obvious. The single-retiree episodes show that emphasis especially clearly, using Roth conversions and cumulative tax charts to frame retirement as a movie rather than a snapshot. Business-owner episodes add another layer, showing how buyer and seller incentives can clash before a deal ever reaches the closing table. The hosts also make space for caution. AI searches, private financial facts, health predictions, family support concerns, and estate-control tools all receive scrutiny rather than hype. The show does not present itself as personal advice, and it repeatedly points listeners back to their own tax, legal, and financial advisors. Its appeal is the combination of specificity and restraint. Big Picture Retirement® gives planning-minded listeners a steadier way to think through complicated retirement choices without pretending that every household should land on the same answer.
Made for: For pre-retirees, retirees, single retirees, business owners, and planning-minded families who want practical context before making major retirement decisions. It best fits listeners comfortable with detailed explanations and advisor-level tradeoffs.
What sets it apart: The show connects retirement questions across legal, tax, and financial domains instead of treating them as separate checklists. Its listener-question format and conversational back-and-forth make technical planning issues feel specific without becoming personal advice.
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.
A Roth conversion becomes a movie here, so you can stop planning retirement from one snapshot.
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Short reviews from the PlayNext desk, based on the episodes we processed.
Devin and John Ross discuss retirement withdrawals, taxes, and what a CD balance can buy after inflation.
Devin and John Ross take up two ways retirement planning can stall: weighing every decision until nothing gets done, and trusting that a savings balance will be enough on its own. They move from that tension to the loose ends that can change what a plan actually delivers.
A Roth conversion can look different when the tax tradeoff is followed year by year.
For a single retiree considering Roth conversions, the final balance tells only part of the story. Devin and CFP Nick Domachowski discuss a client who passed on conversions after seeing when the projected tax savings would break even.
Devin and John Ross explain why buyers and sellers may prefer different ways to structure a business sale.
Devin and John Ross take up a familiar sticking point in a business sale: the buyer may want the assets, while the seller would rather sell company stock. They make the disagreement concrete with equipment.
Paul Haavardsrud unpacks Canadian money stories, from ski-hill VIP pricing to French butter tariffs.
Real-estate freedom, taught in plain numbers.
The hosts discuss the $1.8 billion Powerball jackpot and use it as a springboard to explore estate tax lessons and financial planning for sudden wealth.
Hosts Devin and John Ross discuss why many Americans are claiming Social Security early in 2025 and challenge conventional filing advice.
The hosts discuss the illusion of retirement planning while getting sidetracked by Halloween candy preferences.
The hosts answer a listener's question about whether qualified charitable distributions can be made from a 457 plan, explaining the rules and upcoming changes to 1099 reporting.
The hosts discuss Texas pollen and property taxes before introducing the topic of estate taxes.
A listener asks about using a spendthrift trust for an adult granddaughter who struggles with money management, and the hosts discuss the pros and cons.
Devin and John discuss a recent federal case where a financial executive's AI data was used against him in securities fraud charges.
Devin and John discuss whether knowing your exact death date would be beneficial for retirement planning, concluding it would be emotionally overwhelming.
Devin and John Ross use a GoBankingRates article to sort five retirement loose ends, starting with whether a mortgage, car payment, or even a financed house has to stop someone from retiring.
Big Picture Retirement® centers this episode on tax planning for single retirees and why the same income can be taxed more harshly when brackets are compressed.
Big Picture Retirement® focuses on how to buy or sell a business the right way, with Devin and John Ross saying more than a third of U.S.
This episode covers tax considerations in estate planning, including estate taxes, stepped-up basis, and capital gains.