544: Freedom After 50: Are You Living for Your Resume—or Your Eulogy?
Retire With Purpose - The Retirement Podcast
Casey Weade
4.7 • 556 Ratings
🗓️ 16 January 2026
⏱️ 26 minutes
🧾️ Download transcript
Summary
What if the real measure of a successful retirement isn't what you've built, but who you've been, and how your money supports the life you want to be remembered for?
In this episode, we discuss:
- Resume virtues vs. eulogy virtues
- Why many retirees feel "lost" after achieving everything they worked for
- How purpose changes the way you think about money, work, and time
- Using financial planning to create freedom, not pressure
- Redefining identity, success, and legacy after 50
Today's article is from The Root of All titled, Living for the Eulogy. Listen in as Founder and CEO of Howard Bailey Financial, Casey Weade is joined by Les McDaniel to explore how redefining success through purpose, legacy, and "eulogy virtues" can transform retirement.
Show Notes: HowardBailey.com/544
📧 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 | What if the real measure of success isn't what you've accomplished, but how you'll be remembered? |
| 0:06.0 | Today's conversation is about shifting from chasing achievements to living with intention. |
| 0:20.7 | Hey, this is Casey Weed. Welcome to the show. If you're new to the show, I want you to know what to expect. We're going to be bringing you week in and week out financial and non-financially related conversations with world-class guests. And right now you're joining us for one of our Friday episodes. Every Friday, we bring to you a conversation that comes from our weekend reading for retirees email series. |
| 0:43.4 | So every single Friday, we're sending out this amazing email with four articles that we have curated. |
| 0:49.2 | We have went through hundreds of articles, sifted them down to four articles that we felt were the best to put in front |
| 0:54.8 | of you for this weekend, along with summaries and takeaways for myself, articles spanning everything |
| 1:01.2 | from financial planning concept to the non-financial side of retirement as well. |
| 1:06.1 | So make sure you get the email. And when you do sign up to get the email, I'll also send you a free |
| 1:10.8 | digital copy of my Wall Street Journal bestselling book, Job Optional. All you have to do is text |
| 1:16.0 | us the key letters, W.R. to 888-59-449.1. This is a Freedom After 50 episode today. |
| 1:24.7 | That's on the non-financial side of retirement. So if you're looking for more |
| 1:27.9 | conversations like that, just look for those episodes titled Freedom After 50. And if you're |
| 1:33.4 | looking for more of those numbers related conversations, look for those conversations labeled |
| 1:38.8 | by the numbers. So today I am joined by our retirement coach, our certified retirement coach, financial advisor. I got Les McDaniel here with me today. I am so happy to be here. It's so good to be with you. Well, you picked an article out for us this week. Actually, Marshall picked this article out for us. Did he? He sent it to us, he said, I think you guys should cover this one. I really like it. Okay. We got our By the Numbers guy coming into the heart side of things here. You know, and I think what we're going to do here in the coming weeks is we're going to bring Marshall into this conversation. We're going to do a little three-way conversation and see if we can't bring you an even better conversation with more content. We're going to give that a shot. |
| 2:17.9 | That can be fine. |
| 2:18.4 | If you don't like it, shoot us an email. |
| 2:20.5 | And be nice, though. Be nice. You don't have to, like, rip into us. Yeah. Yeah, tell us. Let us know. We want to know. Or if you love it, write an honest rating and review for the podcast here on iTunes. Now, this article we're going to be discussing today. |
| 2:34.0 | It comes from the root of all |
| 2:37.1 | substack. And so that's a blog, and it is written by Jacob Schroider. I was a little skeptical |
| 2:44.0 | when I saw the article. You send it over. I feel like this happens to me all the time. |
| 2:47.8 | He does. Not just with you. It happens with Marshall, too. Marshall will send me say, well, we should have this conversation. Most of the time, my response |
| 2:54.9 | is, eh, we've done that before. And I had the same response with this one. Yeah. And I have to talk to you |
... |
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