Retirement Answer Man
Roger Whitney, CFP®, CIMA®, RMA, CPWA®
A top retirement podcast. Roger Whitney, CFP®, CIMA®, CPWA®, RMA, guides you on how to actually do retirement well financially and personally. This retirement podcast isn't afraid to talk about the softer side of retirement. It will teach you how to retire with confidence. Two-time PLUTUS winner for best retirement podcast / blog and the 2019 winner for best financial planner blog. This retirement podcast covers how to create a paycheck, medicare, healthcare, Social Security, tax management in retirement as well as retirement travel and other non-financial issues you'll need to address to rock retirement. Retirement isn’t an age OR a financial number. It’s finding that balance between living well today and feeling confident about your retirement. It’s about gaining more freedom to pursue the life you want. Join the rock retirement community at www.rogerwhitney.com
Episodes
Mentioned books
14 snips
Oct 28, 2026 • 56min
How to Interview a Retirement Planner
Tanya Nichols, a financial planner and Retire Agile partner, joins the conversation on choosing and evaluating a retirement planner. Topics include advisor qualifications, fees, fiduciary care, retirement income, healthcare before Medicare, Roth conversions, investment management, and whether to consolidate Vanguard and Fidelity accounts. Social Security estimates, spousal benefits, and delayed claiming also take center stage.
25 snips
Oct 21, 2026 • 47min
Medicare Update with Danielle Roberts
Danielle Roberts, co-founder of Boomer Benefits, helps older adults navigate Medicare. She discusses rising Part D premiums, drug-plan restrictions, Medicare Advantage versus Medigap, open enrollment, and the pitfalls of flashy advertising. Roger also explores building an income reserve before retirement and finding fresh perspective when financial decisions feel overwhelming.
17 snips
Oct 14, 2026 • 44min
Year-End Planning Checklist for Retirees
A practical year-end checkup for retirees, covering spending plans, taxes, Roth conversions, required distributions, charitable giving, and healthcare enrollment. Listener questions explore Social Security survivor benefits, teacher pension choices, unused capital losses, and building confidence to retire. The focus: spot deadlines and avoid costly oversights without turning planning into a major project.
13 snips
Oct 7, 2026 • 1h 4min
The Perfect Portfolio with Peter Lazaroff
Peter Lazaroff, Chief Investment Officer of PlanCorp and author of The Perfect Portfolio, explores why the best portfolio serves your life rather than mathematical perfection. They discuss aligning investments with personal goals, managing risk and uncertainty, indexing versus factor investing, bond strategies, and creating a simple, automated investment process tied to purpose.
14 snips
Sep 30, 2026 • 53min
Your Social Security Playbook: Building Your Strategy- Married Filers
A practical guide to Social Security decisions for married couples. Topics include coordinating benefits, protecting survivor income, balancing early claims against delayed benefits, and avoiding calculator-driven mistakes. Listener questions explore COLA adjustments, military pensions, investment opportunity costs, similar benefit levels, and strategies for a lower-earning spouse claiming early.
12 snips
Sep 23, 2026 • 50min
Your Social Security Playbook: Building Your Strategy- Single Filers
Social Security claiming can feel like a maze, especially for solo filers. Explore common mistakes, a practical OODA framework, and ways to weigh health, taxes, priorities, and survivor benefits. Listener questions tackle switching to survivor benefits, coordinating personal and survivor claims, and estimating benefits after early retirement. Plus, two intriguing book recommendations.
19 snips
Sep 16, 2026 • 52min
Your Social Security Playbook: The Levers You Control
Explore six ways to shape Social Security outcomes, from checking your earnings record and choosing when to claim to managing retirement income, state taxes, and spousal benefits. Listener questions examine benefit uncertainty, different claiming ages between spouses, survivor protection, and whether to draw from retirement accounts while waiting. Compare personalized what-if strategies for a more resilient retirement plan.
6 snips
Sep 9, 2026 • 38min
Your Social Security Playbook: How Your Benefit is Calculated
How does Social Security turn a lifetime of earnings into a monthly benefit? Explore work credits, the 35-year earnings record, indexing, full retirement age, and the trade-offs of claiming from 62 to 70. Plus, a look at survivor and spousal benefits, practical tax estimating, and key resources for reviewing your Social Security statement.
29 snips
Sep 2, 2026 • 55min
Your Social Security Playbook: How the System Works
Social Security takes center stage in a five-week playbook series. Explore its origins, pay-as-you-go funding model, demographic pressures, projected trust-fund shortfall, and possible routes to solvency. Listener questions tackle survivor benefits, early claiming, invested assets, and online claiming tools, along with strategies for building a flexible retirement plan amid uncertainty.
Aug 26, 2026 • 33min
Summer Reruns: Learn What to Ignore with Dr. Daniel Crosby
Daniel Crosby, psychologist and chief behavioral officer known for The Soul of Wealth, helps listeners cut through information overload. He discusses why attention is scarce and how spending reveals true values. Short practical filters are offered to decide what deserves your focus and what can be ignored. The conversation contrasts noise-driven advice with long-term priorities that shape finances and life.
