Retirement Answer Man

If the market outlook has you feeling uncomfortable, you are not alone. This discomfort may cause you to want to change course, but consider that moments of extreme discomfort are often reverse indicators. Extreme discomfort can mean that you are on the right track to grow in a new direction. 

On this episode of Retirement Answer Man, I answer your questions about choosing a financial advisor, how to weather tumultuous financial markets, and using a Roth 401K. Learn what you can do in the midst of an uncertain future by pressing play. 

Is this the big one?

Weathering market downturns can be like weathering a storm. When you are in the thick of it you may wonder if this is the big one that will wreck your home and change your life. Should you just hold on tight and hope that everything will all work out? 

No. No one can hold your hand and assure you that your finances will recover.

The rules of investing change in retirement

The rules of investing when you are in the accumulation period of life don’t work the same in when you are decumulating assets. 

Since you are nearing or already into retirement you don’t have a 40-year investment timeframe to work with, so you may not be around for the next market upswing. You're in a period of life where you will need money from your investments in a short time frame. 

This is why you’ll need a well-thought-out strategy that can help you to stay agile. As the situation unfolds, you can make little adjustments as needed. Staying agile will help you maintain flexibility and retain agency. 

In a situation that feels out of your control, it is important to find ways to retain agency to do what you have to do to control the things that you can. You don’t want to feel powerless, so focus on what you can control. 

Watch out for false prophets

No one can predict what will happen in the future. However, there are many out there that claim that if you follow them they will lead you down the right path. 

We have to accept our own uncertainty and refrain from trying to figure it all out. Instead of trying to predict the future or following false prophets, it is important to create a plan that you can follow to actively navigate through these tumultuous waters which will see you through any eventuality.

How to know when it is time to switch advisors

How can you know if your financial advisor is doing a good job? What are some red flags that indicate that you should reevaluate your relationship with your advisor?

One listener is concerned about his financial advisor since they had two misunderstandings in the last two years and is wondering if he change advisors.

When researching financial advisors look for a specialist that can advise you through your specific financial situation. Consider whether they have the skillset and expertise to handle the problems and opportunities of your specific situation. Do they focus on what you need?

Is your advisor an active thinker that makes decisions or do they simply follow a checklist? Since the decisions that you are making aren’t crystal clear, it is important to have a process to think through decisions in an organized manner. Does your advisor help you with this? Do they walk you through the pros and cons of each decision?

Is the advisor product-focused or process-focused? If they are product-focused then this is a red flag. Another red flag is if they focus on trying to predict what the markets will do. Since no one can predict the future, it is important to find someone who will focus on the things that are within your control. 

Listen in to hear what else you should consider when choosing a financial advisor and when to consider finding a new one. 



  • [3:23] Moments of extreme discomfort are reverse indicators


  • [7:38] Kevin wants to give to the kids while they're still here
  • [12:15] On giving money without strings attached
  • [17:25] Kevin is relearning to show his true colors


  • [19:39] How to know when it is time to switch advisors
  • [34:05] What gives us the confidence that we will recover this time?
  • [41:50] Should Jen switch to a Roth 401K?
  • [48:23] What to use as a yield for net present value calculations


  • [50:07] Experiment with digital minimalism for a week

Resources Mentioned In This Episode

BOOK - The Checklist Manifesto by Atul Gawande

Boomer Benefits

Rock Retirement Club

Roger’s YouTube Channel - Roger That

BOOK - Rock Retirement  by Roger Whitney

Roger’s Retirement Learning Center

Direct download: RAM441.mp3
Category:general -- posted at: 2:00am CDT

We all want to leave a legacy to those we love, but leaving a legacy doesn’t mean simply making a will. To create a lasting financial and nonfinancial legacy you need to have a strategy that you can rely on. Today you’ll learn the steps to take to create a lasting legacy.

Leaving a legacy is different from estate planning

Often times we read about a hot investment or retirement planning tip in an article or hear some equally savory advice in a podcast and we jump to take action on it rather than thinking about how it could fit into our overall plan. I call this letting the tail wag the dog. 

Instead of letting the tail wag the dog, think about your actions first. Stop for a moment and think about how that new shiny idea or product would fit into your overall retirement plan. When you have a goal-based plan in place, it allows you to think through decisions in an organized way. You’ll want to use similar methods to build a plan to create the most impactful legacy that you can.

How to begin creating your legacy plan

There are a couple of steps you can take to begin creating a strategy that will allow you to develop a lasting legacy. 

The first step is to consider what you can afford to do. You can do this by determining how much excess capital you have. This can be a tricky number since there are so many unknowns to consider. These unknowns make it hard to determine how much you will have at the end of your life. 

Consider what is feasible considering your resources and your projected spending. You can gain a better understanding by using a plan of record. If you have never used a plan of record, keep your eyes open for this week’s 6-Shot Saturday newsletter to get a free template. If you aren’t signed up for the newsletter, head on over to to fill out the form and subscribe. 

What are your legacy goals?

Now that you have determined what is feasible given your life vision and resources you can move on to step 2. Consider what kind of financial and nonfinancial impact you want to have. What do you want to accomplish?

Do you want to be able to contribute to your children’s retirement savings? Or maybe you want to help them buy their first home. 

Do you want to create a nonfinancial impact by developing the tradition of having a weekly family dinner? Do you plan on being an exemplar and coaching them through tough choices?

Create intentionality with your legacy strategy by framing it in financial and nonfinancial ways and considering the impact you want to have during and after your life. 

After these first two steps, you can begin to create your strategy. You’ll want to think about maintaining flexibility with your strategy since markets won’t always cooperate with your plans. Your legacy should be built with discretionary money. The tactics will come easy if you focus on creating a strategy first. Listen in to hear how to build your lasting legacy. 



  • [2:43] Doctors don’t want you to engage and ask questions
  • [8:00] Leaving a legacy is different from estate planning
  • [13:17] What impact do you want to have during your life?
  • [18:09] Take time making large stake decisions
  • [25:50] The tactics are easy if you take these previous steps first


  • [27:22] The differences between the representative payee program and advanced designation in Social Security
  • [32:20] How to create a discount factor using a household balance sheet
  • [40:09] My thoughts on taking Social Security at 68 instead of 70
  • [41:25] How the IRMAA brackets work
  • [45:30] Reimbursing your Medicare Part B premiums from your HSA


  • [47:05] Map out what kind of financial and nonfinancial legacy that you want to leave

Resources Mentioned In This Episode

BOOK - Retirement Planning Guidebook by Dr. Wade Pfau


How to Be a Better Advocate for Your Health

LTCI Partners

Rock Retirement Club

Roger’s YouTube Channel - Roger That

BOOK - Rock Retirement  by Roger Whitney

Roger’s Retirement Learning Center

Direct download: RAM440.mp3
Category:general -- posted at: 2:00am CDT

When you think about leaving a legacy do you immediately think about passing on your assets? 

What may be more important than passing on money is leaving behind a nonfinancial legacy to those that you love. Have you considered how you will do this? 

If you would like to leave more than just a trust fund to your family then you won’t want to miss this episode of Retirement Answer Man. You’ll learn about setting a nonfinancial legacy objective, plus strategies, tactics, and more.

Should you panic about a bear market?

I just want to acknowledge that it can be challenging to have confidence in your retirement plan right now. We are now in a bear market which means that stocks are down 20% from their highs. That can give you plenty of anxiety, but since that bear market is paired with decreasing bond prices, this can lead to outright panic. 

Now is the time to reflect on your retirement plan. If you have created an objective-based agile retirement plan you will be able to weather this storm. Have confidence in your strategic plan. 

What is the objective of leaving a nonfinancial legacy?

It will be nice to leave money for your loved ones but wouldn’t you like to leave more? 

To truly leave a legacy you need to be an exemplar. An exemplar is defined as one who serves as a role model or an example. 

Even if there is a gap in where you are in life and where you would like to be, your children and grandchildren are learning how to navigate the world based on your example. They emulate you, so being an exemplar is the best nonfinancial legacy that you can create. 

The more you can encourage others the better exemplar you will be. To encourage means to give courage to someone else. Give your loved ones the courage to lead their best lives. Help them on their journey to be their best selves. You can use finances to help others on their journey but encouragement is even more important.

Strategies to use to leave a nonfinancial legacy

Life is full of the mundane, the day today. But the peaks, pits, and transitions are the flagship moments that we remember. These are the moments that influence how we view the world. If you can help someone during one of these moments in their lives, it may go a long way in transforming their future. 

You can help your community by looking out for these moments in their lives and accentuating them. During the peaks, help them to put an exclamation point on that moment in time so that they can look back and reflect on that high. 

You won’t be able to fix their pits, but you can show up and help them through. 

An encouraging word can help mark transitions in ways that you may not predict.

Fill in the pits. Mark the transitions. Celebrate the peaks. This is how to leave a lasting legacy.

Listen in to hear how you can help your loved ones be the best versions of themselves through your nonfinancial legacy. 



  • [3:22] What is the objective of leaving a nonfinancial legacy?
  • [9:05] Strategies for leaving a nonfinancial legacy
  • [17:55] Tactics for creating a nonfinancial legacy


  • [20:52] How to use a solo 401K
  • [28:28] Should you buy one $10,000 Ibond or multiple smaller amounts?
  • [31:02] The pro-rata rule and Roth conversions
  • [35:35] How can non-sporty people add exercise into their lives?


  • [39:37] Listen to somebody with full presence

Resources Mentioned In This Episode

BOOK - The Power of Moments by Chip Heath

BOOK - Giftology by John Ruhlin

BOOK - Tiny Habits by BJ Fogg

Check out Boomer Benefits, their services are free to you!

Rock Retirement Club

Roger’s YouTube Channel - Roger That

BOOK - Rock Retirement  by Roger Whitney

Roger’s Retirement Learning Center

Direct download: RAM439.mp3
Category:general -- posted at: 5:37pm CDT

We all want to leave a legacy behind after we pass. The legacy you chose to leave is up to you. This episode is part of a 5 part series on leaving a lasting legacy. Today’s episode focuses on leaving a financial legacy. Make sure to look out for the next episode so that you can learn how to leave a non-financial legacy. 

Subscribe to 6-Shot Saturday

We also have the answers to several listener questions on this episode and many others. To submit your own questions for me to answer on the show simply hit reply to the 6-Shot Saturday newsletter. If you aren't subscribed, consider signing up to receive a weekly summary of the show along with any helpful links or tidbits that I find interesting and want to pass along. 

The difference between estate planning and financial legacy 

Estate planning and leaving a financial legacy are not the same. There is a difference between the two. When you pass away you will leave behind property, financial assets, and maybe some liabilities. Estate planning is the official process of closing the books on your financial life. If you leave behind more assets than liabilities then those assets will have to go somewhere. The probate process spells out how that will work. 

You get to decide how to distribute your assets. When deciding who will receive your assets it is important to analyze the outcomes you are trying to achieve. This process is the way to leave your financial legacy. 

Planning the outcomes 

If you are married, it is important to ensure that your surviving spouse financially secure. That is usually the first consideration in leaving a financial legacy. 

Those that have children often choose to leave their legacy to their children, others choose to leave their bequeath to friends or charitable organizations. It is important to remember that if you don’t approve of the financial trajectory that one of your children is on, you don’t have to enable their poor behaviors. You get to choose who to bless with your assets and how. You do not have to support behaviors that you don’t want to support. There are strategies you can use to help your family while at the same time protecting them from themselves. 

There are obstacles that could stand in the way of achieving the financial legacy outcomes that you desire. Our culture makes discussing money a taboo subject. This could stand in the way of the outcome you seek. Many people avoid planning their legacy and choose to ignore this type of plan. A lack of planning will mean that you won’t achieve the outcome you seek. 

Strategies and tools to leave a financial legacy

When you pass you’ll want to transfer your assets as efficiently as possible. While a will is the first tool that you should have in place, many people are surprised to realize that a will is not that efficient since it must pass through probate. There are other ways that you can pass your assets on to those you love without having to go through the probate process. 

A living trust is a revocable trust that bypasses probate. The trust document not only states who receives the assets, but it can also define how those assets are managed.

Another way to efficiently manage your financial legacy is through beneficiary designations. By designating your beneficiaries in your IRAs and 401Ks these assets will bypass probate and flow to your chosen beneficiaries. Make sure that you revisit your beneficiaries regularly to ensure that they are up to date.

Listen in to hear tactics you can use to leave your legacy both during your life and beyond. 



  • [3:20] Estate planning and leaving a financial legacy are not the same
  • [6:13] What outcomes do you want?
  • [10:45] Obstacles to the outcomes
  • [12:14] Strategies and tools to use to leave your legacy
  • [17:48] Tactics to use to leave a legacy during your life
  • [23:12] The ways you could give


  • [26:08] Dave’s question on investment classes
  • [35:44] What exactly is the market?
  • [40:11] Carl’s question on selling a large position in one stock


  • [44:15] Be courageous. Act in the presence of fear

Resources Mentioned In This Episode

LTCI Partners

Make sure that you are signed up for the 6-Shot Saturday newsletter!

Rock Retirement Club

Roger’s YouTube Channel - Roger That

BOOK - Rock Retirement  by Roger Whitney

Roger’s Retirement Learning Center

Direct download: RAM438.mp3
Category:general -- posted at: 10:00pm CDT

Have you considered the legacy you will leave to those whose lives you touch? Does leaving a legacy need to be financial or something more? 

This month we explore how to leave a lasting legacy in an organized way. You’ll learn the ways that you can leave an enduring legacy during your life and beyond. 

Today we are defining legacy and noodling on what that means both financially and non financially. Next week, we’ll discuss the different strategies that you can use to leave a financial legacy, the following week we’ll explore non-financial legacies, and in the 4th episode of this series, you’ll learn how to create your own legacy strategy. 

Live a life true to yourself

Some people are spurred into retirement because they have trouble compartmentalizing work and so it bleeds into other areas of their lives. They choose retirement to escape the pace of a grueling work life.

However, many high performers experience a lot of guilt upon retirement. They may feel an obligation to their team or their clients to continue working and feel held back by other people’s expectations, but living a life true to yourself means letting go of others’ expectations. 

Learn how to not just survive retirement, but gain the confidence to rock retirement. Sign up for the 6-Shot Saturday newsletter to receive a weekly email with a summary of the answers to the questions from the show, plus links, tools, books, and other resources that will help you on your retirement journey

What do you think of when you hear the word legacy? 

When you hear the word legacy do you simply think of money or does legacy mean something more? 

My mom died young–she was only 48 when she passed. When I think back on her legacy I don’t consider the check I received from the lawyer a few months later. Instead, I am reminded of our conversations and debates on how best to live life. You could say that this podcast is an indirect result of her legacy. 

Mom insisted on living a life of delayed gratification so that she could save for the future–a future that she never got to enjoy. I argued that living life in the present was the way to go. However, finding a balance between living well today and delaying gratification is the best way to live a life without regret. Ultimately, that is what this podcast is all aobut. 

What does legacy mean? 

The dictionary defines legacy as money or property given in a will, or something handed down from an ancestor. 

When you die you will leave a legacy. What you choose to leave behind is up to you. 

A nonfinancial legacy includes lessons, memories, and experiences that you share with others. How are you actively working to build a nonfinancial legacy in retirement? 

A financial legacy could be money, property, or other mementos that generally come to your loved ones in a sterile way. A financial legacy could give your heirs the financial fuel they need to get started or continue on their journey through life. Make sure to tune in next week to hear what tools you can use to build your financial legacy. 



  • [5:35] What do you think of when you hear the word legacy?


  • [14:48] A Daily Stoic blog post
  • [16:14] Responses to Wendy’s question about postponing travel
  • [19:03] A Roth conversion question from Joel
  • [22:22] Joe’s question on planning for inflation
  • [27:12] What should Joe’s CFP be doing in response to the current market conditions?
  • [33:02] Where I learned to fly fish in Colorado


  • [34:17] Expand your thinking on legacy

Resources Mentioned In This Episode

Legacy Is Not for You from the Daily Stoic blog

Boomer Benefits - check out their FREE 6-day mini-course!

Episode 429 - Should I Retire Earlier If I Have Health Issues?

IRS Publication 505

Rock Retirement Club

Roger’s YouTube Channel - Roger That

BOOK - Rock Retirement  by Roger Whitney

Roger’s Retirement Learning Center


Direct download: RAM437.mp3
Category:general -- posted at: 2:00am CDT