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
13 snips
May 13, 2026 • 39min
Decluttering for Retirement: How a Simpler Life Helps You Rock Retirement
The conversation explores how simplifying possessions, finances, and relationships creates mental space and reduces overwhelm. It examines the limits of risk tolerance questionnaires and suggests building portfolio buckets from purpose and time horizon. Practical tips cover consolidating accounts, donor-advised funds, trimming digital inputs, and writing down personal motivations to stick with decluttering.
29 snips
May 6, 2026 • 50min
Decluttering for Retirement: It's More Than Cleaning Out Your Closet
A fresh series reframes retirement as a chance to reset identity and shed what holds you back. Topics include emotional letting go illustrated by a car sale story, physical belongings and heirlooms that anchor past lives, financial clutter like scattered accounts, and relationship obligations that steal time. The show ends with listener questions and a seven-day awareness sprint to inventory things, money, and people.
35 snips
Apr 29, 2026 • 58min
How Long Will You Live After Retirement?
Dr. Bobby Du Bois, physician and longevity coach who advises on cardiac risk and dementia considerations, joins to rethink how long to plan for. They explore lifespan assumptions, mortality trade-offs for money versus time, using actuarial and cardiac tools to personalize estimates. Practical steps and a simple framework help you choose conservative or moderate planning horizons.
15 snips
Apr 22, 2026 • 48min
Listener Questions: How Do I Create a Diversified Portfolio?
Clear breakdown of diversification vs market risk and why asset allocation matters most. Practical rules for building portfolios and the four inputs that drive allocation decisions. A three-bucket retirement plan for contingency, liquidity, and growth. Pros and cons of allocation funds, S&P 500 vs total market, and the buy-borrow-die strategy. Short, actionable review to refine your retirement plan.
20 snips
Apr 15, 2026 • 48min
Listener Questions: What Should I Be Doing When I'm Two Years from Retirement?
Practical steps for the two-years-out retirement timeline. Clear guidance on handling inflation risk and hedging strategies. How to design your retirement life first, then map income from Social Security and pensions. Tips on positioning accounts, building after-tax cash for flexibility, and timing Roth conversions to reduce tax and Medicare surprises.
Apr 8, 2026 • 42min
Listener Questions: Should I Take Social Security Early and Invest It?
A lively discussion about whether to claim Social Security early and invest the benefits. Short mathematical scenarios explore how investment returns and lifespan change the outcome. Clear reasons for claiming early versus delaying are weighed. Practical tips on inherited Roth moves, avoiding 401(k) fees, and downloading your Social Security statement are highlighted.
Apr 1, 2026 • 43min
Listener Questions: Should I Move My 401K into an IRA When I Retire?
They discuss whether to roll a 401(k) into an IRA and the key reasons for keeping or consolidating retirement accounts. Health insurance and budgeting for out-of-pocket retirement costs get practical attention. The limits of retirement planning software and how AI can act as a thinking partner are explored. The show also highlights meaningful travel stories and a seven-day experiential gift challenge.
29 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.
