Retirement Answer Man

Rosie and Dwayne retired in a bear market and now they wonder if they will have enough money to rock retirement. We will explore that question all month long in this Retirement Plan Live. 

Over the course of the next few weeks, you’ll learn about Rosie and Dwayne and their journey, their goals, their resources, and their investment strategy. Then we’ll wrap up this series together with a live webinar on February 2. Don’t miss out on the exciting finale, sign up at

Meet Rosie and Dwayne

Rosie and Dwayne live a fairly simple lifestyle. They don’t own a big house or drive flashy cars. They don’t take lavish vacations or eat at fancy restaurants. Although they live simply they do have their own retirement dreams.

When Rosie retired a year and a half ago she figured the worst of the Covid debacle was behind her. She had seen the flash bear market, but since then, the markets seemed to be doing well. Unfortunately, within a year of retiring, she watched her assets decrease by 25%. Now she is left wondering if she’ll ever be able to live out her retirement dreams. 

Rosie and Dwayne both worked in the IT sector before Covid hit. While Rosie was able to work from home, Dwayne was laid off and has since begun flexible part-time work. Working from home simply enticed Rosie to fully dive into retirement. 

What Rosie loves about retirement

Rosie loves the time freedom that retirement brings. She has plenty to do to keep busy: spending her days with her grandkids, at the pickleball court, going to exercise classes, and cooking. Rosie is a natural organizer and creates a weekly plan complete with to-do lists. 

Enjoying the love of family and friends and traveling are what brings her joy and how she desires to spend her time in retirement. 

Rosie’s fears about retirement

With Covid and the subsequent bear market, Rosie feels that she is missing out on fully enjoying retirement. She is very aware of the passing years and understands that time is precious. She feels frustrated that she may not have enough time to do all the things that she wants to do and go to all the places she wants to go. 

Her financial situation is much different than it was a year ago although that hasn’t caused her to change her spending habits. She’s trying not to let her emotions drive her decision-making. 

Rosie understands that she needs a clear mind and that she should stay the course that she and her husband laid out with their financial advisor. While she understands that logically, she is still concerned about their future.

Over the course of this series, Rosie is looking for more input and a better understanding of what changes she needs to make to ensure that she can live out her retirement dreams.

You can follow along with Rosie by using the Agile Retirement Planning process

Follow along over the next four episodes to hear how we use the Agile Retirement Planning process to discover if she and Dwayne are really ready to live out their retirement dreams.

As we work through this Retirement Plan Live series you can follow along and participate in your own retirement plan with the same helpful worksheets that Rosie is using to guide you on your way. Make sure that you are signed up for the 6 Shot Saturday email newsletter to get each week’s worksheet delivered to your inbox. 



  • [1:35] Just say no to New Year’s resolutions


  • [6:05] Let’s meet Rosie
  • [15:17] What Rosie thinks about retirement so far
  • [23:56] What makes her most frustrated
  • [26:54] How retirement has been financially
  • [30:45] Rosie’s top ten values


  • [38:44] Is there an optimal balance among the allocation between tax categories
  • [43:43] How to factor a whole life insurance policy into your retirement plan
  • [47:51] The max limits to a 457 and 403B
  • [50:42] Is it ever better to take Social Security at 62?


  • [54:33] Make daily resolutions to improve your energy, work, and relationships

Resources Mentioned In This Episode

Morningstar The Long View podcast #186 - Roger Whitney: Retirement Planning Is Not Financial Planning

Rock Retirement Club

Roger’s YouTube Channel - Roger That

BOOK - Rock Retirement  by Roger Whitney

Roger’s Retirement Learning Center

Direct download: RAM468.mp3
Category:general -- posted at: 2:00am CDT