541: Your 2026 Reset: The Best of the Retire With Purpose Podcast
Retire With Purpose - The Retirement Podcast
Casey Weade
4.7 • 556 Ratings
🗓️ 2 January 2026
⏱️ 38 minutes
🧾️ Download transcript
Summary
What can our top five Retire With Purpose Podcast episodes of 2025 teach you about avoiding regrets, spending confidently, and living with purpose as you head into 2026?
In this episode, we discuss:
- The most common retirement regrets
- How to generate flexible, reliable income in retirement
- The Surplus Bucket Strategy and why it can help spending confidence
- How to understand your level of retirement readiness
- Why delaying joy can come at a higher cost than you think
Listen in as Founder and CEO of Howard Bailey Financial, Casey Weade kicks off the new year with a "Best Of" episode to reflect on the best moments from 2025 by revisiting the insights that resonated the most with you, the listener, this past year.
Show Notes: HowardBailey.com/541
📧 WEEKEND READING FOR RETIREES: Receive CFP® insight on 4 hand-picked financial articles delivered straight to your Inbox each Friday: https://bit.ly/3OEdGgu
📅SCHEDULE YOUR PERSONAL FINANCIAL REVIEW: Book a 15-minute call with Howard Bailey Financial to see how the topics discussed here apply to your individual situation: https://bit.ly/3T6oNDB
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 | Welcome to the Retire with Purpose podcast. My name is Casey Weed and happy new year. As we step into |
| 0:06.8 | 26, I wanted to start the year off a little differently. Instead of jumping straight into something |
| 0:12.9 | brand new, I want us all to take a moment to reflect because sometimes the most powerful |
| 0:19.3 | insights come from revisiting the conversations |
| 0:22.0 | that resonated the most. I know for me, one of my favorite phrases is it's not always |
| 0:27.3 | about learning something new, but remembering something true. And today's episode is just about |
| 0:33.7 | that. It is our best of the Retire with Purpose podcast from 2025, a collection of our |
| 0:39.5 | top five episodes of the past year. These are the conversations you listened to, shared, and |
| 0:45.6 | came back to again and again. In this episode, you're going to hear short clips from each show, |
| 0:51.7 | and if one really hits home, you can listen to the full episode by searching |
| 0:55.9 | the episode number and title wherever you stream your podcast. The five episodes were top five |
| 1:02.2 | retiree regrets and how to avoid them comparing four flexible income strategies for retirement. |
| 1:08.1 | The surplus bucket strategy, a way to spend more confidently in retirement, |
| 1:12.5 | levels of retirement readiness, where do you stand, freedom after 50, the hidden cost of delayed |
| 1:18.6 | gratification in retirement, whether you're listening on a walk, in the car, or sitting with a cup |
| 1:23.7 | of coffee. |
| 1:24.4 | I'm glad you're here. |
| 1:25.7 | Let's jump in. |
| 1:38.6 | Music with a cup of coffee. I'm glad you're here. Let's jump in. All right. So we have the regrets of retirees. We're starting with number one, which is so |
| 1:42.4 | obvious, not saving enough. Yeah, of course, |
| 1:45.7 | that's going to be their regret that gets pointed out as number one. We haven't saved enough |
| 1:49.3 | for retirement. And I go, yeah, I know, I know I'm supposed to save more for retirement. I've heard |
... |
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