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Retire With Purpose - The Retirement Podcast

573: The Life Transition Every Retiree Must Learn to Master

Retire With Purpose - The Retirement Podcast

Casey Weade

Education, Business, Self-improvement, Investing

4.7564 Ratings

🗓️ 3 July 2026

⏱️ 20 minutes

🧾️ Download transcript

Summary

Retirement isn't just about leaving your career; it's about learning how to navigate one of life's biggest transitions with confidence and resilience. As part of our "Freedom After 50" series, best-selling author Bruce Feiler shares why the most fulfilling retirements come from embracing change instead of resisting it.

Topics covered in this episode: 

  • Why retirement is often a "lifequake," not just a life event
  • The three phases everyone experiences during major life transitions
  • How to avoid getting stuck after retirement
  • How couples can navigate retirement transitions together
  • A simple exercise to identify where you are and what you need most

Listen in as Founder and CEO of Howard Bailey Financial, Casey Weade and Bruce Feiler provide thoughtful insights and advice on how it applies to your unique financial situation.

Show Notes: HowardBailey.com/573

📧 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

Click on a timestamp to play from that location

0:00.0

Most of us were taught to expect a linear life, school, work, retirement, stability.

0:06.7

Bruce Filer says life is not linear anymore, and the people who thrive are the ones who learn how to move through disruption with purpose.

0:16.7

Bruce is one of America's leading voices on life transitions, family meeting, and ritual.

0:22.4

His newest book, A Time to Gather, explores how rituals help people and families reconnect in a time of disconnect.

0:37.2

Bruce, welcome back.

0:39.1

Casey, it's nice to be with you.

0:40.3

Thank you for inviting me.

0:41.5

I'm excited to get into this series with you.

0:44.5

I know we have a few different episodes that we're going to do.

0:46.7

We're going to cover some of the things we talked about previously,

0:49.2

but I know you're working on some new stuff as well,

0:51.5

so I can't wait to get into that.

0:52.9

But I want to start at the

0:54.6

beginning, and I think we have a great flow for these different episodes that are going to be

0:58.9

released. I really think in sequential order, and I really felt like it made sense for us to start

1:04.4

these conversations around life transitions. I might say, you may not say this yourself,

1:10.1

but you're the master of life transitions. So let's, you may not say this yourself, but you're the master of life

1:11.1

transitions. So let's start with misunderstandings around life transitions. What do most people

1:17.2

misunderstand around life transitions? I think that the number one thing that people misunderstand

1:24.2

is that we think that all of the change that we're all experiencing every day.

1:30.8

Like, everybody listening to us has the sense of, like, I'm off track or off kilter,

1:36.7

like the life I was expecting to live is not necessarily the life I am living.

...

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