571: You've Saved for Retirement — So Why Does Spending Still Feel Wrong?
Retire With Purpose - The Retirement Podcast
Casey Weade
4.7 • 564 Ratings
🗓️ 19 June 2026
⏱️ 24 minutes
🧾️ Download transcript
Summary
You've accrued wealth to finally retire, but your "best" retirement involves learning how to enjoy the life your wealth was meant to support. As part of our "Freedom After 50" series, hospice doctor Jordan Grumet explores how to discover what truly brings you fulfillment once money is no longer the main objective.
Topics covered in this episode:
- The emotional transition from accumulation to retirement
- Why reaching financial independence doesn't automatically create peace of mind
- The 3 phases of spending and how expectations often clash with reality
- Ways to spend with confidence while staying aligned with your values
Today's article is from the The Purpose Code blog titled How I Finally Stopped Caring About Spending. 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/571
📧 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 | Why do so many people spend 30, even 40 years building wealth, only to feel uncomfortable |
| 0:05.0 | actually using it? If you've ever felt guilty spending money, even when you know you can |
| 0:10.6 | afford it, today's conversation is for you. |
| 0:39.6 | Welcome to the podcast. My name's Casey. It is my mission to deliver clarity and purpose and elevate meeting in your life. Now, if you're new to the show, you might be wondering what that means. Well, we're bringing you conversations that are both financially related and non-financially related for this retirement phase that you may be approaching or already in in your life. If you're seeking out those conversations that are strictly |
| 0:44.7 | financially oriented, look for those episodes titled by the numbers. If you're looking for that |
| 0:49.4 | non-financial content, look for those episodes titled Freedom After 50, which is what you're |
| 0:53.4 | joining for today. |
| 0:55.5 | And most of these conversations that we release on Friday, they actually tie back into an article |
| 1:00.7 | that we included in our weekend reading for retirees email that comes out every single Friday, |
| 1:05.7 | four articles on trending topics to keep you up to speed. So to get on that list and also get a free copy of |
| 1:13.0 | my Wall Street Journal bestselling book Job Optional, all you have to do is text us the key letters |
| 1:17.2 | WR to 888-599-4491, which gets you a link to get signed up, or you can also check out a link |
| 1:24.6 | in the show notes as well or the description of the podcast. |
| 1:28.7 | Today we are talking to Dr. Jordan Grumman. |
| 1:33.1 | Dr. Jordan Grummet is the author of several books we've discussed on the show with him in the past. |
| 1:39.9 | He is also the host of the Earn and Invest podcast and his substack, The Purpose Code. |
| 1:45.2 | I encourage you to check it out. |
| 1:46.6 | We include a lot of his content in our weekend reading. |
| 1:50.1 | So I'm excited to talk a little bit more about one of those posts that he had with him personally. |
| 1:55.4 | It was titled, How I Finally Stopped Caring About Spending. Jordan, welcome to the show, and I'm sure everyone's |
| 2:04.7 | wondering, how do you just not care about spending? Well, here's the thing. I realized that worrying |
| 2:12.6 | about spending made me miserable. It made me miserable when I didn't have money. It made me miserable when I did have money. And it made me miserable when I started concentrating on spending because I thought it was going to make me happy. I came to this weird conclusion. I have an unhealthy relationship with money. And specifically, I think spending is going to make me happy and it almost never does. |
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