542: By the Numbers: From Fear to Freedom — Learning How to Spend in Retirement
Retire With Purpose - The Retirement Podcast
Casey Weade
4.7 • 556 Ratings
🗓️ 9 January 2026
⏱️ 36 minutes
🧾️ Download transcript
Summary
You saved diligently for decades — so why does giving yourself permission to spend still feel so hard?
In this episode, we discuss:
- Why many retirees underspend despite having a secure financial plan
- Emotional and psychological barriers to spending
- How lifelong, "saver" habits impact retirement decisions
- Low-risk strategies to help build spending confidence
Today's article is from the Kitces blog titled, Helping Underspenders And "Savers" Understand They CAN Spend More With 4 Stages Of "Experiments". Listen in as Founder and CEO of Howard Bailey Financial, Casey Weade, breaks down the article and provides thoughtful insights and advice on how it applies to your unique financial situation.
Show Notes: HowardBailey.com/542
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ABOUT HOWARD BAILEY FINANCIAL: Our mission is to help others gain clarity in purpose and elevate meaning in their lives through personal and practical financial strategies. Our Retire With Purpose™ Framework starts with establishing your unique financial philosophy — the true meaning and purpose for your money in retirement. Through continued education, one-on-one meetings, and a comprehensive team planning approach, we have helped retirees across the country secure their financial futures. And while we can't work with everyone, our goal is to provide value to everyone we meet. Our team of advisors and support specialists strive to deliver the very best experience in pre-retirement and retirement planning. Learn more about our process here: https://howardbailey.com/our-process
Transcript
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| 0:00.0 | Research shows that underspending in retirement is far more common than most people realize, |
| 0:05.6 | even among households with strong financial plans. |
| 0:09.3 | Today, we break down the psychological roadblocks behind that behavior and what you can do to move from security to satisfaction. |
| 0:17.6 | Music to satisfaction. |
| 0:31.3 | Hey, this is Casey and welcome to the Retire with Purpose podcast. |
| 0:35.7 | Where does my mission deliver clarity and purpose and elevate meaning in your life? |
| 0:37.9 | If you're wondering what that means, maybe you're new to the show. I want you to know what to expect moving forward. We have both financial and |
| 0:43.4 | non-financially related conversations here on the podcast with world-class guests and every single |
| 0:49.1 | Friday. We're bringing you a short form conversation that alternates between the financial and the non-financial. |
| 0:56.0 | If you're looking for those non-financial episodes, I encourage you to look for those episodes titled Freedom After 50. |
| 1:02.7 | If you're looking for those that are a little bit more by the numbers, well, look for those episodes titled by the numbers. |
| 1:08.7 | And that is what we're doing today. |
| 1:10.9 | When we join you on Friday, we're usually discussing an article in greater depth that is part of our weekend reading for retirees email series. |
| 1:19.8 | So every single Friday, we release an email to our subscribers with four articles on trending topics all designed to keep you on top of the best |
| 1:30.2 | in investment strategy, income strategy, tax strategy, but also the latest research on the non-financial |
| 1:36.1 | aspects of this next phase of your life. We'll deliver to you those articles along with |
| 1:40.8 | summaries, takeaways from myself. And if you sign up, we'll also send |
| 1:45.4 | you a free digital copy of my Wall Street Journal bestselling book, job optional. All you have to do |
| 1:50.5 | to get signed up is to text us the key letters, WR to 888-59499491. We'll send you a link to get |
| 1:58.7 | yourself signed up so that you can receive that weekly email, dive in deeper, and get the other three articles. |
| 2:04.7 | Today we are discussing an article that was written by our good friend over at Kittsies, Michael Kitsy, and that is the kitts.com blog, also known as nerds, I view. |
| 2:16.0 | And the article is titled Helping Unders Spenders and Savers |
... |
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