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Retirement Answer Man

Replay: Overcoming Frugality in Retirement with Dr. Dan Crosby

Retirement Answer Man

Roger Whitney, CFP®, CIMA®, RMA, CPWA®

Lifeplanning, Retirementplanning, Financialplanning, Saving, Careerplanning, Self-improvement, Education, Retirementpodcast, Investing, Business, Investmentmanagement, Retirement

4.71.1K Ratings

🗓️ 23 July 2025

⏱️ 29 minutes

🧾️ Download transcript

Summary


In this enlightening episode, we tackle the often overlooked mental shift required in retirement: transitioning from a saver to a spender. Join us as we revisit a compelling conversation with Dr. Daniel Crosby, Chief Behavioral Officer at Orion Advisory Services. We'll explore the psychological barriers many face in letting go of frugality and how to embrace the resources they've accumulated to enhance their lives. Discover practical strategies to gain confidence in spending, overcome the fear of uncertainty, and ultimately, live a fulfilling retirement without the regret of dying with too much money. Tune in for insights that could transform your approach to retirement!

*This episode originally aired March 20, 2024

OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN

  • [00:30] Overcoming frugality is a major crisis for many in retirement

INTERVIEW WITH DAN CROSBY

  • [01:19] Roger introduces Daniel Crosby.
  • [02:50] How do we overcome frugality?
  • [04:30] There are a lot of behavioral things that change when you leave full-time work.
  • [09:45] How to gain confidence in the midst of uncertainty.
  • [17:22] People are wired to avoid regret.
  • [18:01] What are some basic things people can do to overcome frugality?
  • [22:16] You can't undo 40 years of programming in 4 minutes- experiment with behavior and small commitments.

TODAY’S SMART SPRINT SEGMENT

  • [25:15] In the next seven days, I challenge you to examine your retirement plan and ask yourself- is there something else I should add that’s important to my life?

RESOURCES

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Transcript

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0:00.0

One of the aspects that's often shortchanged in retirement planning is the internal work necessary to adjusting from being a saver to being a spender.

0:14.0

Boy, ain't that the truth? It's all in our heads, baby. Welcome to the show dedicated to helping you not just survive retirement, but to have the confidence

0:22.2

to lean in and rock retirement. Overcoming frugality and doing the mental work to give yourself

0:31.8

permission to use resources to create a great life, so you don't die with too much money,

0:40.7

is a major crisis for many people in retirement, especially those that by good fortune and hard work, et cetera, have the

0:45.5

means to do so. And today, we're going to revisit a conversation we had with Dr. Daniel

0:51.2

Crosby on overcoming frugality.

0:54.7

We're going to talk about how to gain confidence in the midst of uncertainty,

0:58.8

because there's always reasons to not spend money and ways that we can overcome frugality

1:05.1

in order to lean into the kind of life we want to create.

1:09.1

So let's dive in with Dr. Daniel Crosby.

1:15.9

So we're here at Daniel Crosby, Chief Behavioral Officer at Orion Advisory Services.

1:23.0

Daniel, how are you? Great. Great to be here, Roger. I appreciate you hanging out with me on this 10th anniversary month, which is sort of insane to think about.

1:32.4

Ten years thinking about one subject is been one of the best things I've ever done, not just professionally, but personally, of focus.

1:40.5

Today, I wanted to explore with you one of the threads that I've found along the way that I've been pulling in trying to find frameworks to help people empower themselves.

1:53.9

So we think of retirement crisis as people not having enough for retirement, which is a huge crisis.

1:59.5

That is the main crisis.

2:01.0

Yeah. It really is. But there's also another crisis, which is sort of feels uncomfortable to talk about,

2:06.4

but it's a crisis of people that have been successful either through, well, a combination of effort,

2:11.9

effort and serendipity and luck and all that, of accumulating enough wealth. And when you become a really good accumulator and you've done it for decades, it has,

2:23.2

I would imagine, a self-fulfilling loop of affirmation and comfort, etc.

2:29.5

And I've discovered a lot of these people have a hard time harvesting and using, in this case, their financial

...

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