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Investing · Roger Whitney, CFP®, CIMA®, RMA, CPWA®

Retirement Answer Man

by 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

Latest episodes

Showing 20 · updated from the feed

Your Social Security Playbook: Building Your Strategy- Single Filers

#27 trending · Business

Roger Whitney explains how solo filers can make a confident Social Security claiming decision without getting overwhelmed by complexity. He covers the biggest mistakes to

Sep 23
50 min

Your Social Security Playbook: The Levers You Control

Roger Whitney explains six levers that can influence Social Security benefits: reviewing your earnings record, choosing when to claim, managing retirement income, reconsi

Sep 16
52 min

Your Social Security Playbook: How Your Benefit is Calculated

How is your Social Security benefit actually calculated? In this episode, Roger explains how you qualify for retirement benefits, how your earnings history determines you

Sep 9
37 min

Your Social Security Playbook: How the System Works

Social Security is one of the most important pieces of a retirement plan, but how does the system work, and will it remain financially viable for future retirees? Roger b

Sep 2
54 min

Summer Reruns: Learn What to Ignore with Dr. Daniel Crosby

In this summer replay, Roger talks with Dr. Daniel Crosby about learning what to ignore in an age of information overload. They explore how to filter financial advice, al

Aug 26
32 min

Summer Reruns: Gabbing with Gretchen Rubin- Your Personality and How it Plays into Your Retirement Planning

This Summer Replay revisits Roger’s 2018 conversation with Gretchen Rubin about the Four Tendencies and how understanding your personality can help you create a retiremen

Aug 19
21 min

Summer Reruns: Keep Investments Simple with Peter Lazaroff

As part of Roger’s summer replay series, he revisits a conversation with Peter Lazaroff about the value of elegant simplicity in retirement investing. They discuss why mo

Aug 12
41 min

Summer Reruns: Retiring Single with Tanya Nichols

August is encore month on the Retirement Answer Man podcast, giving Roger an opportunity to step back, reflect, and revisit some of the show's most impactful conversation

Aug 5
24 min

Retirement Toolkit: Never Worry About Money Again with Jesse Mecham

What if budgeting wasn't about restriction, but about giving every dollar a purpose? This week, Roger sits down with Jesse Mecham, founder of YNAB (You Need A Budget), to

Jul 29
1 h 05 min

Retirement Toolkit: How do you Balance Optimization with Simplification

How do you know when it's worth optimizing your retirement plan and when it's better to keep things simple? This week, Roger answers a listener question by exploring Aris

Jul 22
53 min

Retirement Toolkit: How to Rebalance a Retirement Portfolio

This week Roger explains why rebalancing is one of the most important disciplines in retirement planning. In the Retirement Toolkit, he explores the difference between a

Jul 15
55 min

Retirement Toolkit: How Does Step Up in Cost Basis Work

This week Roger talks about one of the biggest challenges retirees face today: information overload. He explains why more information doesn't always lead to better decisi

Jul 8
49 min

Retirement Toolkit: How Required Minimum Distributions (RMDs) Work

This week Roger explores the idea of "digging where your feet are" and how focusing on what you can do today can reduce anxiety about the future and regret about the past

Jul 1
45 min

IRMAA: The Medicare Premium Surprise and How to Avoid It

This week Roger breaks down IRMAA Medicare surcharges and why retirees should understand them without letting them dominate retirement planning decisions. He explains how

Jun 24
49 min

Mutual Funds vs. ETFs- Which is Better for Retirement?

This week, a simple quote about wasting time sparks a deeper conversation about why retirement isn't meant to be endlessly optimized. In the Retirement Toolbox, we compar

Jun 17
1 h 04 min

Know What You Pay: A Guide to Investment & Advice Costs

Roger Whitney explores the relationship between cost and value in retirement planning, focusing on how to better understand the fees associated with financial advice, inv

Jun 10
41 min

Take the Retirement Leap of Faith with Jordan Grumet

Roger Whitney explores the idea that retirement always involves both excitement and uncertainty. While people spend years gathering information, running projections, and

Jun 3
58 min

Decluttering for Retirement: Your Step-by-Step Plan

In this episode, retirement expert Roger Whitney and Marie Kondo consultant Dr. Lindsey Hardegree explore the transformative power of decluttering. They discuss how clear

May 27
1 h 01 min

Decluttering for Retirement: Why It's So Hard and How to Push Through

Roger Whitney continues the decluttering series by focusing on the hidden challenges that keep people stuck. Rather than treating decluttering as a massive life overhaul,

May 20
44 min

Decluttering for Retirement: How a Simpler Life Helps You Rock Retirement

Roger Whitney continues the decluttering series by exploring the opportunities that come from simplifying your life, finances, and relationships. He explains how reducing

May 13
39 min

Chart trend

Position in the Investing chart (US), last 90 days.

#31
all-time peak
186
days in the top 50 since Nov 2024

Chart positions

Where Retirement Answer Man ranks today in each Apple Podcasts chart (US, Sep 24, 2026).

#172 ▲ 10 Business US
#44 ▲ 18 Investing US

What listeners say

A curated, balanced selection of Apple Podcasts reviews.

Timely and varied information to round out the retirement experience. One of the trifecta of retirement podcasts with the others being The Retirement and IRA Show and Retirement Planning Education

PJM-NYC · Jul 2026

I so appreciate Roger’s knowledge and perspective. This podcast helps build and maintain your nest egg, sure. But Roger also helps me think through the personal and ethical implications of my decisions, in an exceedingly non-judgmental way. And he helps listeners improve the quality of their retired years, beyond their net worth.

debh · Jun 2026

This episode starts with a “what if I know nothing” approach, and built up to a much more sophisticated Q and A for an investor with a $10M portfolio. That’s what I love about these >600 episodes. There is always a new nugget you can build upon if you can stomach the redundancy (or fast forward). It reinforces sound advice about Timeframe and building the 3 key buckets: Contingency, liquidity, and growth funds. Thanks Roger

Semi-Retired in Colorado · Apr 2026

There are a lot of podcasts out there, but if you’re starting the think about retirement (or have already retired) this is my favorite. Roger covers the technical and emotional needs as one shifts from accumulating wealth to decumulation, and never loses focus on enjoying that retirement.

J@(& · Dec 2025

Looks like this podcast is going the route of other good podcasts which is increasing the length. Last 2 sessions are over 1 hour with this week 1.5 hours. About 2x longer than it should be. Was a good podcast but simply isn’t worth that investment of time. It’s a shame because I enjoyed it.

Johhny64 · Oct 2024

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