Retirement Answer Man

This is our last episode of 2022, so naturally, there will be a bit of reflection alongside the practical planning and your listener questions. Kevin Lyles also joins me in the Coach’s Corner to discuss living your best life in retirement. 

Let’s noodle on what it means to live authentically and discover the answers to some fantastic questions that will help guide you on your retirement journey. Stick around until the end of the episode to hear my word for 2023 and how I plan to review my year. 

Be the author of your hero’s journey

To be authentic literally means to be your own author. That’s what planning your retirement journey is all about. By building a framework to rock retirement you are writing your own story. 

I’m excited to wake up each day and help give you ideas to write your retirement story. By being the author of your own life you will be authentic and live without regret. To start the new chapter of your life consider where you are on your journey. The hero’s journey framework can help you navigate so that you can figure out what is important to you. 

Don’t miss the call to adventure

The hero’s journey is a cycle of constant death, rebirth, and renewal. Some version of you has to die before you can become reborn into your new self. 

If you haven’t retired yet then you are still in Act One of the hero’s journey. In this first act you are being called to something other than your full-time career. Being called to an adventure can be a powerful force. It is a force so powerful that oftentimes our first response is to resist the call. 

However, if you embrace the call you can find mentors to help you along the way. These mentors can come in the form of books and podcasts and they can be people who are further along in their journey that you can look to answer questions along the way.

Act Two requires a leap of faith

To step into Act Two you must take the leap of faith. As you journey into retirement this means stepping away from your old life and into the unknown. Along the way, you’ll face allies and enemies, but you cannot know the trials and ordeals you will encounter throughout this adventure. 

You’ll need a framework to help you navigate Act Three 

In our Third Act of your hero’s journey, you will overcome the trials and ordeals, but only if you have a framework to help us along the way. This is where I come in. Building that framework to help you through the trials and tribulations of retirement is what this show is designed to help you do. I aim to be your mentor and ally along the way.

Some version of this journey plays out in different ways throughout our lives. I’m excited to begin this new chapter with you. We’ll be focusing on building out the financial plan, but as you know, a financial plan alone isn’t the only thing you need to conquer this journey and rock retirement. I look forward to helping you build your retirement in the new year and beyond. 



  • [3:24] The hero’s journey


  • [9:01] How to live your best life in retirement


  • [19:07] What a yield curve is and why it matters
  • [20:42] Should I take my pension lump sum now or later?
  • [26:35] Ron’s experience living overseas
  • [29:56] Use the Social Security website to help optimize
  • [31:07] Can I take outside IRAs and roll them into my 401K?
  • [35:22] What should Doug do to help his spouse handle finances when he passes
  • [37:51] Whether to take small pensions now or later


  • [41:08] Choose your word for 2023

Resources Mentioned In This Episode

Joseph Campbell 

The Heroic App

Rock Retirement Club

Roger’s YouTube Channel - Roger That

BOOK - Rock Retirement  by Roger Whitney

Roger’s Retirement Learning Center

Direct download: RAM467.mp3
Category:general -- posted at: 2:00am CDT

Do you wonder what you’ll do with all your free time in retirement? Planning your time by filling your days with purpose and passion can help ease the stress that comes with the sudden emptiness of leaving behind a full-time career. 

On this episode of Retirement Answer Man, we’ll discuss how dabbling in a few different activities can help you find your purpose. You’ll also hear the answers to questions posed by listeners like you.

Coming soon to a podcast app near you: Retirement Plan Live!

Are you ready for the next Retirement Plan Live? Beginning January 4, we’ll return to our most awaited annual series. The next RPL will feature Rosie and Dwayne, a couple that retired with already constrained assets during a bear market. While helping Rosie create her feasible plan of record, I’ll also help her understand how to handle retirement in a bear market and what she can do next to help her through this challenge. 

If this will be your first Retirement Plan Live series, or even if you are a veteran RPL listener, I encourage you to listen to the entire series and join us for the live webinar at the end of January so that you can get a true sense of how the agile retirement planning process works. 

Filling your suddenly empty itinerary in retirement can feel daunting

I recently had a conversation with someone who was considering holding off on retirement because they didn’t know what they would do without the routine of work in their lives. 

We begin our social conditioning from the time we start school. School helps to begin to define the external structures of our lives by giving us a place to go, a reward system, a social network, and a vacation structure. This system continues as we enter our working years which makes it a challenge to suddenly leave this lifelong system and venture into the unknown. 

Try dabbling in something new

Since retirement completely blows up the structure and rhythm of life, it can be intimidating to step out into the unknown and venture forth without a plan. 

Having a purpose in retirement can help you transition into something new. However, not everyone knows what their purpose will be. 

Dabbling in a few areas can be one way to try out new interests. In the way that many kids dabble in various sports and artistic activities when they are young, we can do so as well as we approach retirement. By dabbling in a few different activities you can see what fits without becoming overly invested in one particular area. 

Should Suzy buy out her husband’s portion of their shared rental property?

Suzy has been going through a divorce for the past several years and is ready to finally financially settle. One of their shared assets is a $4 million property that could be used as a short-term or long-term rental. The property needs about $500,000 worth of work and it would require a $2 million loan to buy her husband out, so she is trying to decide whether it makes sense financially to take on such a mortgage at this stage in her life. 

To ensure that Suzy makes the best decision she can, it is important for her to consider what she wants her life to be like in the future. There are multiple pathways we can take in life so it is important to envision your future before jumping into any permanent decisions. 



  • [3:18] How to rock life outside the financial realm
  • [11:03] What to do to set yourself up for some structure


  • [13:25] What to do with Suzy’s rental property in her divorce
  • [20:24] How the widow’s Social Security works
  • [22:13] If I delay Social Security will I get the COLA increase as well?
  • [23:55] Should I stop contributing to my 401K?


  • [30:10] Dabble with something

Resources Mentioned In This Episode

Rock Retirement Club

Roger’s YouTube Channel - Roger That

BOOK - Rock Retirement  by Roger Whitney

Roger’s Retirement Learning Center

Direct download: RAM466.mp3
Category:general -- posted at: 2:00am CDT

Are you curious about the changes that are coming next year on the Retirement Answer Man show? Today, you’ll have a sneak peek at one of our new segments: the Rock Life segment. Bobby Dubois joins me to discuss how to ensure that you have enough energy so that you can rock retirement. 

On this episode, you’ll also hear my holiday gift-buying suggestions as well as the listener questions segment. Don’t miss out on hearing what to do with a settlement, whether to file for Social Security if you are still working, and whether you should simplify your investments in retirement. 

Don’t miss this episode to hear the answers to these listener questions, get a preview of what’s to come next year, and to get some fantastic gift ideas. 

My holiday gift guide

Buying and receiving gifts later in life can be challenging since many of us already have so much. I prefer to give experiences over anything else, but when an experience isn’t appropriate a game is my go-to gift. These are some of the games that I enjoy playing or might make great gifts for someone you love

Sequence - easy enough for the whole family to enjoy

Quix - a fast-paced dice game

Euchre - a midwesterner’s favorite

Left Center Right - this can actually be played with dice or cards

Ticket to Ride - a longer board game that’s worth learning

Pictionary - great for parties

Scattergories - another classic party game

Kids Against Maturity - a twist on Cards Against Humanity that might be more appropriate for the family

Play Nine - when golf meets cards

Tri-Ominos - a triangular domino game

Listen in to hear what our listeners recommend. One listener has a fantastic tip for learning new games. 

Should James apply for Social Security while still working full-time?

James is still working and approaching full retirement age. He would like to apply for Social Security but continue to work yet he is confused by the whole process. There isn’t much information about collecting Social Security while working full time. 

An added complication is that signing up for Social Security will automatically enroll him in Medicare. However, he still has healthcare coverage through his employer and would like to continue his employer’s coverage. 

James is right. There isn’t much information about collecting Social Security and enrolling in Medicare while still employed full-time. And what is out there is really confusing. 

You can collect Social Security at full retirement age while still working. The financial ramifications may push you into a higher tax bracket. 

Boomer Benefits can help you navigate Medicare’s complexities

One aspect of choosing to collect Social Security at full retirement age is that it will automatically enroll you in Medicare part A. Parts B and D can be delayed, but they must be turned on within eight months of leaving your employer-sponsored health plan. The good news is that Medicare part A will coordinate with your health insurance if you end up hospitalized. 

Since there are so many difficulties in navigating this question, I recommend that anyone in this situation contact a Medicare navigator like Boomer Benefits.

Boomer Benefits is a company that deeply understands Medicare and the entire enrollment process. They don’t charge the consumer and aren’t trying to sell you anything–they are simply trusted advisors. They have numerous educational resources both on their website and on YouTube.



  • [1:34] Roger’s holiday gift buying guide


  • [10:30] Should James file for Social Security if he is still working?
  • [14:10] What to do with a settlement
  • [23:10] Whether to simplify investments
  • [29:20] If I just retired can I still make a Roth contribution?


  • [30:37] The 3 pillars to building energy in our lives
  • [34:32] Intentionally observe what works for you


  • [45:00] Go buy a game or experiment on yourself

Resources Mentioned In This Episode

Cozy Earth - enter RAM at checkout to receive a 35% discount!

Boomer Benefits

Boomer Benefits on YouTube


Oura Ring

Stacking Benjamins

Rock Retirement Club

Roger’s YouTube Channel - Roger That

BOOK - Rock Retirement  by Roger Whitney

Roger’s Retirement Learning Center

Direct download: RAM465.mp3
Category:general -- posted at: 5:53pm CDT

Is it worth investing in individual stocks or should you simply go with ETFs? Joe has recently parted ways with his financial planner and is beginning to manage his portfolio himself and was wondering about the benefits of these choices. 

Tanya Nichols and I will explore Joe’s questions as well as others on this episode of Retirement Answer Man. Listen in to hear the benefits of owning ETFs vs individual stocks, how to structure your Roth conversions, and what to do about health insurance before Medicare. 

Making decisions is rarely a cut-and-dry process

When making decisions, we usually look for a clear answer: yes or no, do it or don’t do it, jump or don’t jump. However, judgment calls are rarely so simple. Usually, we are operating without all of the pertinent information, so we have to make assumptions about how the future will look. 

The process of brainstorming is messy. There is no crystal clear way to go about making decisions, and once you do you probably won’t know if you chose correctly. 

When confronted with choices you’ll want to have a framework to explore decisions in an organized way. Then you’ll want to relax and consider all the options. When you take the pressure off you’ll have more opportunities to come to a good decision. Next, dive into the process and see what comes. You may explore several different scenarios before coming upon your final decision.

What I’m reading

My strategy for reading this year has been to make reading my default activity. Reading is what I go to when I’m waiting in line, have spare time at home, or when I’m taking a walk (via audiobooks, of course!). This new mindset has led me to read 33 books so far this year. Today I wanted to share with you the most recent books I have read and my thoughts on them. 

Boys in the Boat by Daniel James Brown is an inspiring book that I highly recommend. It chronicles a member of a crew team in the 1920s and 30s and his life journey from childhood and then on to the 1936 Olympics. 

Quit was written by Annie Duke the author of Thinking in Bets. Annie was a professional poker player turned decision-making expert. In this volume, she examines how hard it is to quit something once you have started.

Put Your Ass Where Your Heart Wants to Be by Steven Pressfield is a fast read–you could finish it in a day. This is a great book that helps people work on challenging goals. This book will help you get past the resistance. 

Courage Is Calling by Ryan Holiday is a book that will enrich your soul. 

It Takes What It Takes was written by Trevor Moawad who was a performance coach for elite athletes. This book on mental conditioning promotes the thesis that if you want to be great at something you have to make a choice to do the things to make you great. Making the choice to be exceptional clears the path to greatness because it takes everything else off the table. 

The Dichotomy of Leadership by Jocko Willink was written for leaders on the aspects of finding the virtuous mean. 

If you have any great book recommendations I’d be happy to hear them. Just head on over the Ask Roger page and leave an audio suggestion or write it in. 



  • [1:23] On making decisions
  • [4:11] What I’ve been reading


  • [19:33] Should Joe invest in individual stocks or ETFs
  • [27:36] What to put in Roth conversions
  • [32:45] What should Todd do about insurance between the ages of 58 and Medicare?
  • [42:22] Looking for resources on the ex-pat life


  • [44:38] Treat people as they could be

Resources Mentioned In This Episode

Align Financial

BOOK - Boys in the Boat by Daniel James Brown

BOOK - Quit by Annie Duke

BOOK - Put Your Ass Where Your Heart Wants to Be by Steven Pressfield

BOOK - Courage Is Calling by Ryan Holiday

BOOK - It Takes What It Takes by Trevor Moawad

BOOK - The Dichotomy of Leadership by Jocko Willink

Phil Stutz

Rock Retirement Club

Roger’s YouTube Channel - Roger That

BOOK - Rock Retirement  by Roger Whitney

Roger’s Retirement Learning Center


Direct download: RAM464.mp3
Category:general -- posted at: 2:00am CDT