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
Mar 25, 2026 • 60min
Why Even the Best Retirement Calculator is Wrong
They dig into why Monte Carlo retirement tools can give misleading confidence and what those success rates actually measure. They contrast complicated vs complex problems and warn against substituting software for judgment. They list what planning tools miss, the many hidden assumptions, and how to read outcome distributions and timing of failures. They offer practical best practices for using calculators as guides, not decision-makers.
7 snips
Mar 18, 2026 • 1h 1min
Retirement Talk with Dr. Wade Pfau
Wade Pfau, retirement researcher and author of The Retirement Planning Guidebook, explains the RISA assessment and why it outperforms typical risk questionnaires. He explores real estate and reverse mortgages as retirement tools. He digs into annuities — timing, inflation protection, and fixed index products — and untangles tax timing, ACA subsidy cliffs, and how software models retirement outcomes.
Mar 11, 2026 • 50min
Healthcare Before Medicare: Retiree Feedback
Practical strategies for handling health coverage before Medicare, including timing COBRA and ACA transitions. Real retiree tips like part-time work benefits, company retiree plans, and creative risk-sharing approaches. Survey highlights on subsidy use and warnings about Medicaid or policy changes. Quick action on identifying supportive people for retirement planning.
Mar 4, 2026 • 1h 8min
How to Feel Loved with Dr. Harry Reis
Dr. Harry Reis, social psychologist and professor who studies close relationships, shares research-backed ways to deepen connection and belonging. He explains the seesaw model for reciprocal sharing. Short, practical mindsets like listening to learn, radical curiosity, multiplicity, and gradual vulnerability are highlighted. Live Q&A tackles one-sided talks, love languages, and moving toward more face-to-face connection.
Feb 25, 2026 • 46min
Healthcare Before Medicare: Creating Your Own Action Plan
Taylor Schulte, retirement planner and founder of Define Financial who focuses on retirement healthcare and tax strategies. They discuss using a step-by-step OODA framework to organize five-year cashflow and MAGI estimates. Short-term bridges like COBRA, ACA cliffs, and trade-offs between Roth conversions, Social Security timing, and simplicity get practical attention.
Feb 18, 2026 • 53min
Healthcare Before Medicare: How to Lower Your Costs
Practical ways to lower health costs before Medicare by staying healthy, timing care, and shopping prescriptions. Clear comparisons of coverage options like COBRA, part-time employer plans, and private policies. A plain breakdown of how ACA premium tax credits and the 400% federal poverty level cliff affect premiums. Tips on managing MAGI, withdrawal tactics, and avoiding surprises at tax reconciliation.
10 snips
Feb 11, 2026 • 45min
Healthcare Before Medicare: Your Options
A clear tour of pre-Medicare health care options, from using COBRA as a temporary bridge to navigating ACA marketplace plans. Practical tips on checking provider networks and enrollment rules are highlighted. Creative alternatives like part‑time employer coverage and cautionary notes about private plans and health‑share arrangements are discussed.
Feb 4, 2026 • 42min
Healthcare Before Medicare: What Happens When You Retire Before 65?
A clear look at the three biggest healthcare problems retirees face when leaving employer coverage. Short segments on sticker shock from lost employer subsidies and the tax effects of paying premiums from IRAs. Discussion of narrowed provider networks and tough tradeoffs to keep trusted doctors. A walkthrough of complex ACA choices, subsidy interactions, and practical planning steps to review your healthcare assumptions.
10 snips
Jan 28, 2026 • 28min
Retire on FIRE: Rocking an Early Retirement- The Challenges of Retiring Early
Listeners in their 50s–70s share reflections on purpose, work, health, and the changing seasons of retirement. Stories explore balancing financial readiness with enjoying memorable experiences now. Practical tips cover health plan shopping, maintaining marketable skills, finding meaningful projects and community, and serving others to create lasting purpose.
Jan 21, 2026 • 48min
Retire on FIRE: Rocking an Early Retirement- Henry and Lucy's Resources
Henry and Lucy dive into the realities of early retirement, exploring pivotal trade-offs and their emotional hurdles. They confront the challenge of giving up earned income and navigate the complexities of Social Security assumptions. The couple outlines their after-tax assets and strategies for financial independence. Listeners are treated to personal insights about sabbaticals and the importance of intentionality in retirement, leaving them with actionable advice and a renewed sense of confidence in their own journeys.
