Retirement Answer Man

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