Retirement Answer Man

Making retirement decisions brings plenty of questions and over the next month, I’ll be tackling your retirement questions. While I love answering your questions, I also enjoy hearing your thoughts. In today’s episode, there are a couple of questions that I’d love to hear your feedback on. If you have any thoughts to share with other listeners please respond to the 6-Shot Saturday newsletter. If you’re not signed up, head on over to and scroll down to the bottom of the page to get weekly tips, news, and resources in your inbox every Saturday morning.

Deciding to spend large sums of money in retirement can be unnerving

Early on in retirement is when people want to have the most fun, but it can also be the most daunting time to spend money. Even if the numbers say that you’ll be ok financially, you can never be certain if you may need that cash when you’re 90. Making the decision to spend large amounts of money in retirement can be daunting.

I got to thinking about decision-making recently when I wrote the biggest check I have ever written. This check will (hopefully) be an investment in my business, but it was still a difficult decision to make that took a lot of thought and counsel from others. 

How I employ my own decision-making tactics

I actually practiced what I preached and used the same decision-making process that I teach on the show. I started with my vision by projecting where I want to be in the future. I thought about how this decision fits into my long-term goals for myself and my company. Then, I got to thinking about the result that I hoped for as well as the worst-case scenario. 

I seek the counsel of others

Since I know I have blind spots in my own decision-making when it comes to myself and my business, I enlisted the help of others to bounce my ideas off of. I started with my wife, Shawna, then sought counsel from Nichole, and others that understand my situation. I encouraged them to challenge my assumptions and poke at my blind spots. We walked through alternatives and discussed opportunity costs. Ultimately, it was up to me to make the judgment call. I won’t know for quite some time whether I made the right decision, however, I know that the process that I used to make this decision was sound. 

With the right process, you can be secure in your decision making

I share this with you, because you may be wondering if you should spend $30,000 to take an epic family trip next year, buy that vacation home, or RV across the country. The memories you create may be well worth the money, but you won’t know if you made the right choice until you reach the end of the road. Nobody can tell you what the correct decision will be for you, but if you work through your decision in an organized way starting with your vision then you’ll know that you made the best decision that you could. 

Speaking of big decisions, Wendy is trying to decide whether to increase her savings now that she and her husband will be empty nesters. Or should they continue to save for retirement at the same rate while taking time to travel and enjoy more of life now while they are both still healthy? Listen in to hear the details of her situation and then let her know what you think by responding in our 6-Shot Saturday newsletter. What would you do if you were in her shoes?



  • [1:32] My process as I work through a big decision


  • [11:05] Daniel’s comment on needs, wants, and wishes and my response
  • [14:22] A consideration on relocating in retirement
  • [17:10] Travel now or increase savings and retire early?
  • [20:50] Bond accrual structural strategy
  • [22:24] A Roth conversion question
  • [26:06] On retirement regret


  • [31:46] Check out our decision-making worksheet in 6-Shot Saturday

Resources Mentioned In This Episode

Boomer Benefits

PODCAST - Deep Questions with Cal Newport 

Episode 402 - The Tax Toolbox with Andy Panko

Episode 416 - Retirement Plan Live: Why We Moved

Episode 426 - How to Plan Your Agile Retirement: A Feasible Retirement Strategy

BOOK - Wooden: A Lifetime of Observations and Reflections by John Wooden 

BOOK - Born Standing Up by Steve Martin 

BOOK - So Good They Can’t Ignore You by Cal Newport

BOOK - Unstoppable Teams by Alden Mills

BOOK - Antifragile by Nassim Nicholas Taleb

BOOK - The Way I Heard It by Mike Rowe

BOOK - How to Decide by Annie Duke

BOOK - Grit by Angela Duckworth

Rock Retirement Club

Roger’s YouTube Channel - Roger That

BOOK - Rock Retirement  by Roger Whitney

Work with Roger

Roger’s Retirement Learning Center

Direct download: RAM429.mp3
Category:general -- posted at: 2:00am CST