568: The 4 Emotional Phases of Retirement with Fritz Gilbert
Retire With Purpose - The Retirement Podcast
Casey Weade
4.7 • 564 Ratings
🗓️ 5 June 2026
⏱️ 21 minutes
🧾️ Download transcript
Summary
What happens when the retirement you worked so hard for doesn't feel as fulfilling as you imagined, and how can you rediscover purpose, structure, and joy in this next chapter of life?
As part of our "Freedom After 50" series, topics covered in this episode include:
- Why the "honeymoon phase" of retirement eventually fades
- Why curiosity may be the single most important retirement skill
- Practical ways to experiment, reinvent yourself, and find purpose again
- How retirees can avoid getting stuck in the "lost and loss" phase
- Why retirement planning should include far more than finances
Today's article is from The Retirement Manifesto titled, The 4 Phases of Retirement. 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/568
📧 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 | Today, I'm joined by my friend Fritz Gilbert, the founder of the Retirement Manifesto, |
| 0:13.7 | an award-winning blog dedicated to helping people achieve a great retirement. |
| 0:18.9 | You have probably heard Fritz on the show before, and today is going to be a |
| 0:24.1 | treat. We're going to be discussing the four emotional phases of retirement. Most people imagine |
| 0:29.0 | retirement as a finish line. The day the alarm clock goes away, the calendar opens up, and every |
| 0:34.7 | day just feels like Saturday. But what happens when every day really is Saturday? |
| 0:40.9 | And it stops feeling special. |
| 0:42.6 | Well, Fritz is going to talk to us about those four emotional phases of retirement, why the honeymoon phase eventually ends, and how to avoid getting stuck in what some retirees describe as the lost years. If you're new to the show, |
| 0:57.2 | I want you to know what to expect. My mission here is to deliver clarity and purpose and elevate |
| 1:01.4 | meaning in your life. And if you're not sure what that means, well, stick around. We bring you |
| 1:06.9 | both financial and non-financial related conversations week in and week out. |
| 1:10.9 | If you're looking for those more financially oriented conversations, look for those |
| 1:14.4 | episodes titled by the numbers. |
| 1:16.5 | If you're looking for those non-financial topics, then look for those titled Freedom |
| 1:20.1 | After 50, and that's what you've joined us for here today. |
| 1:22.9 | And always accompanying these conversations, we have an email that goes out every Friday with four |
| 1:29.2 | articles, update you on the things that I am reading that I want to keep in front of our audience. |
| 1:34.7 | And also, if you've never signed up before, we'll send you a free digital copy of my Wall Street |
| 1:38.7 | Journal bestseller job optional. To get signed up, just text us the key letters WR to 888-599-4491. With that, let's get into it. Fritz, |
| 1:50.2 | welcome back, my friend. Casey, nice to see you again, man. Appreciate you having me on. |
| 1:54.6 | Hey, it's always a riot getting together with you. And I know our listeners always enjoy the kind of concepts you bring to the |
| 2:02.8 | table because, hey, real-life retirees tend to have that real-life experience that you can't get |
... |
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