Retirement Answer Man

Retirement can be tricky. There are so many unknowns, so preparing yourself mentally can be a challenge. 

Mental toughness is the ability to remain positive and proactive in the most adverse situations. Our Retirement Plan Live volunteer, Rosie, is having to rely on mental toughness to stay on target through an extra challenging early retirement.

Join Rosie and me today as we discuss the impact that the bear market had on her finances at the start of her retirement. 

Rosie is trying to get her retirement back on track

Rosie and her husband Dwayne didn’t retire in the best circumstances. Inflation and market fluctuations haven’t been on their side. This sequence of returns at the beginning of their retirement is not faring well for their portfolio. Now they are trying to assess whether they are on a feasible path or whether they’ll need to make some adjustments. 

Simply by walking through this process they are already being proactive. They are assessing the damage and seeing how they can shape a plan for the future to get back on track. 

It’s challenging to enjoy the go-go years without a safety net

While Rosie is more risk-averse, her husband Dwayne enjoys researching and investing in individual stocks. He uses about 10% of their total savings to play around in the market investing in his favorite publicly traded companies. 

Rosie estimates that about 75% of their total portfolio is in stocks and this makes her feel a bit anxious especially since their portfolio is down about 20% from last year. 

She would like to be enjoying her go-go years, however, without a healthy cash reserve in place, or a long-term care plan, she doesn’t have the security in place to let loose and rock retirement.

Without a cash bucket set up, their $8,500 per month is coming from a systematic selling of their investments, but she’s not sure where they should go from here. 

Don’t miss the culmination of the past four episodes

If your retirement isn’t going to plan, it is important to acknowledge where you are now so that you can mitigate the damages and reset your course. You can’t simply ignore the situation and wait for someone to tell you that everything is going to be okay. You’ll need to understand the nuances of your financial situation to determine the best way forward. 

Join us on February 2 at 7 pm CST for the grand finale of this year’s Retirement Plan Live. I’ll walk Rosie through her retirement plan and we’ll determine whether or not it is feasible. Then we’ll look for risks and opportunities. As a participant, you’ll have the opportunity to ask questions and see how the process plays out. 

After the live meetup, consider joining the Rock Retirement Club. The Club was created to give new retirees a solid framework and trusted tools to use to build a feasible, resilient retirement plan that will give members the confidence to rock retirement. In addition, RRC members have created an amazing, inviting community filled with people on the same journey. Learn more by joining the live meetup. 



  • [4:47] Rosie’s questions
  • [7:12] Understanding Rosie’s annuity
  • [16:52] Understanding the software we use
  • [18:32] Understanding the sequence of returns risk
  • [27:07] Rosie’s experience with advisors


  • [36:36] Do you calculate using tax-deferred dollars to create a paycheck in retirement?
  • [44:32] Using a draw-down strategy for a 401K
  • [47:57] How to get a better interest rate from cash


  • [50:40] Reassess your trajectory to achieving your goals

Resources Mentioned In This Episode

Join the live meetup on February 2 at

Money Guide Pro Elite retirement tool

New Retirement Calculator

Rock Retirement Club

Roger’s YouTube Channel - Roger That

BOOK - Rock Retirement  by Roger Whitney

Roger’s Retirement Learning Center

Direct download: RAM471.mp3
Category:general -- posted at: 2:00am CDT

Take a breath, check yourself, and then observe where things are at. 

That’s what Rosie and I are doing on this episode of Retirement Plan Live.

After the last episode in which Rosie planned out all her hopes and dreams for retirement, today we’re taking a look at her financial picture. We’ll walk through the sources of her social, human, and financial capital to see where she and her husband stand financially. 

Listen in and create your own plan as we go. Make sure to sign up for 6-Shot Saturday to ensure that you get all the worksheets to work through your own retirement plan with me and Rosie.

Sign up for the grand finale on Feb 2, 2023

Have you signed up for the live webinar on February 2? This will be the grand finale to this year’s Retirement Plan Live. We’ll see if Rosie’s dream retirement is feasible with her resources. We’ll also identify potential risks and opportunities that she should watch out for. Head on over to LiveWithRoger to register. 

How will Rosie pay for those retirement dreams?

We can never know anything for certain, about our financial future, but we can build a solid framework to build up our confidence in our plan. Last week, Rosie laid out her retirement goals and as she did so she tied those into her values. Our goals are really just a representation of our values. 

As we walk through Rosie’s finances we analyze three different types of capital: social, human, and financial. Social capital includes guaranteed payment sources. The most familiar example of social capital is Social Security. Rosie and Dwayne don’t have any pensions, but Rosie is collecting $2200 per month from Social Security. Soon Dwayne will also receive $1800 per month from Social Security as well. In about six years they will begin to receive a small annuity payment. 

Dwayne is the one providing human capital with his flexible part-time work online. This work contributes between $15-20,000 per year. He plans to continue working part-time for about six more years. 

Their financial capital includes $30,000 in after-tax assets, $680,000 in pre-tax assets, and $55,000 in tax-free assets. 

Build your net worth statement as you listen

Listen in to hear what other kinds of assets Rosie and Dwayne have as we walk through building a net worth statement. When was the last time you updated your net worth statement? 

January is a great time to observe where you are financially so that you can marshall your resources to ensure that you can achieve your goals. As Rosie and I build her net worth statement you can too. 



  • [4:20] Their social capital
  • [6:30] Their human capital
  • [7:35] Their financial capital
  • [9:02] Their other assets


  • [15:54] A Social Security error - who to call?
  • [19:36] What can Sarah do to get closer to retirement under less than ideal circumstances?
  • [24:00] How to know if benefits will continue to increase


  • [26:56] Update your net worth statement

Resources Mentioned In This Episode - overpayment

Social Security episodes 228229230231232

Rock Retirement Club

Roger’s YouTube Channel - Roger That

BOOK - Rock Retirement  by Roger Whitney

Roger’s Retirement Learning Center


Direct download: RAM470.mp3
Category:general -- posted at: 2:00am CDT

Setting big goals is great, but they have to be the right goals or else they could become a trap. Rosie joins us again today to set her retirement goals. In this episode, you’ll hear her financial goals for her needs, wants, and wishes. We’ll discuss her financial expectations for each of these categories and how her goals fit into her values. 

Don’t miss out on this second episode of Retirement Plan Live. When you finish listening, head on over to to register for the live meet-up on February 2 where we will break down Rosie’s plan in detail and decide whether or not she’ll be able to live out her retirement dreams. 

Goals must be driven by values

In the previous episode, you met Rosie and learned about her situation and her values. We start each Retirement Plan Live series with values because values are what drive our goals. If you set your goals up too rigidly or shoot for the wrong goals then you are working toward something without really desiring it.

Goals are important to have because they framework of what you are trying to achieve. Listen in to learn how Rosie uses her values to drive her goals. 

What makes a base great life? 

What does it take to build a base great life? The base great life is the line in the sand that you can’t cross. It is what you need to have in place to secure a basic life worth living. 

Rosie estimates that it would take about $5000 per month (excluding healthcare costs) to live her base great life. Listen in to hear what she includes in her base great life and why this doesn’t mean eating rice and beans every day. 

Rosie’s wants and wishes

Rosie values travel and would love to spend about $24,000 per year for the next 5 years on travel expenses. After that, she estimates that she would continue to travel but would slow down on spending but still spend around $15,000 per year for the following 8 years. 

Other discretionary expenses would include $10,000 per year on eating out more frequently and spending on loved ones. Adding in these extra wants and wishes would take Rosie and her husband about $117,000 per year.

Follow along and create your own agile retirement plan 

This week, I encourage you to look at your retirement goals with fresh eyes so as not to limit your thinking. Really hone in on what it takes to build your base great life, then add in the layers that build up your wants and wishes. Shed away your inhibitions as you consider your wishes category.

As you listen to Rosie’s journey, why not follow along for yourself? Make sure you are signed up for the 6-Shot Saturday newsletter to receive the corresponding worksheets for each episode. Every week during the Retirement Plan Live series we’ll send out a worksheet to help you work through each stage in the agile retirement planning process. 



  • [4:03] What is a base great life?
  • [10:45] Discretionary spending


  • [25:33] Can Tim’s wife retire?
  • [32:37] Can Crimaud collect Social Security without a green card?
  • [35:25] How to work in tithing in retirement


  • [40:38] Revisit your needs, wants, and wishes

Resources Mentioned In This Episode

Collecting Social Security in Canada

Rock Retirement Club

Roger’s YouTube Channel - Roger That

BOOK - Rock Retirement  by Roger Whitney

Roger’s Retirement Learning Center

Direct download: RAM469.mp3
Category:general -- posted at: 2:00am CDT

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