485: Top 5 Retiree Regrets and How to Avoid Them
Retire With Purpose - The Retirement Podcast
Casey Weade
4.7 • 564 Ratings
🗓️ 21 February 2025
⏱️ 26 minutes
🔗️ Recording | Apple Podcasts | RSS
🧾️ Download transcript
Summary
You want to ensure you have all your ducks in a row before entering retirement. Today, we're pulling back the curtain on the biggest retiree regrets so that they don't become yours too.
In this episode, we discuss:
- Do you need to be a millionaire to retire?
- The Social Security "breakeven" number
- Pros and cons of bringing debt into retirement
- Preparing for a forced retirement
Today's article is from The Retirement Manifesto titled, 5 Top Regrets of Retirees (and how to avoid them). 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/485
📧 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/3z5mXIw
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 | On today's show, the top regrets of today's retirees and steps that you can take to avoid them. |
| 0:14.5 | Hey, this is Casey Weed, and it is my mission here on the podcast to deliver clarity and purpose and elevate meaning in your life. |
| 0:23.7 | If you're new to the show, I want you to know what to expect. We have wide-ranging conversations on a variety of different topics. |
| 0:29.7 | It's not all about the numbers here at Retire with Purpose. We like to discuss both the financial and non-financial aspects of life in retirement and life |
| 0:39.2 | over 50. If you're looking specifically for some of that non-financial content, I'd like to point |
| 0:44.5 | you to our freedom after 50 episodes with our certified retirement coach, Les McDaniel. |
| 0:50.7 | And today I am joined by my good friend and fellow certified financial planner for a |
| 0:55.9 | little bit more of a financial conversation. I have Marshall Johnson here with me. Hey, hey, |
| 0:59.9 | what's up, buddy? Hey, we are going to be covering a weekend reading article. And that weekend reading, |
| 1:05.2 | what is weekend reading? Well, weekend reading, this is a resource you have to get signed up for. |
| 1:09.4 | We send out an email every single |
| 1:11.4 | Friday. My team and myself, we go out, we do the work, we sift through all the garbage on |
| 1:15.7 | the internet and find you some gold. And we deliver to you four different articles on a variety |
| 1:21.2 | of different topics, all designed to elevate your life in retirement. You have summaries and |
| 1:25.4 | takeaways from myself. And you also have a litany of other |
| 1:28.4 | resources that are going to end up in that weekend email. So make sure you get yourself signed up. |
| 1:33.0 | And if you've never signed up before, we'll send you a free digital copy of my Wall Street Journal |
| 1:37.0 | bestselling book. Job optional. Just text the key letters, WR to 888-599-4491, and we will get you signed up to get that weekly email. Today, we are |
| 1:49.5 | going to be discussing a article, our blog post, written by one of my favorite podcast guest, Fritz Gilbert. |
| 1:57.3 | Yes, sir. I highly encourage you. Check out his blog. If you've been on weekend reading list for a while, we love Fritz. |
| 2:03.6 | And we like to include a lot of Fritz Gilbert content in those weekly emails from time to time, |
| 2:08.6 | because there's just a lot of gold that he puts out. |
... |
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