560: By the Numbers: Can You Really Beat the Market by Avoiding the Worst Days?
Retire With Purpose - The Retirement Podcast
Casey Weade
4.7 • 556 Ratings
🗓️ 17 April 2026
⏱️ 26 minutes
🧾️ Download transcript
Summary
What if trying to avoid the market's worst days is actually one of the fastest ways to sabotage your retirement plan?
Topics covered in this episode:
- Why best and worst market days often occur back-to-back
- The math of gains vs. losses — and why it's not equal
- The "lost decade" and what it teaches investors
- Why avoiding bad years matters more than avoiding bad days
- How reduced volatility strategies can stabilize retirement outcomes
Today's article is from Morningstar titled You Can Beat the Stock Market by Avoiding Its Worst Days. But You Won't. 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/560
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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 avoiding just a handful of bad days in the market could dramatically improve your returns, even double them? |
| 0:06.7 | Well, today, we're testing that theory and exploring how it really impacts your retirement income strategy. |
| 0:27.0 | Welcome to the Retire with Purpose podcast. It is my mission to deliver clarity and purpose and elevate meaning in your life. And if you're not sure what that means, well, stick |
| 0:31.2 | around, find out, explore some of our other episodes. Week in and week out, we provide you a |
| 0:36.8 | variety of different types of content, |
| 0:38.6 | both financial and non-financial. You're always going to want to look out for those episodes |
| 0:42.8 | titled Freedom After 50 if you're interested in that non-financial type of content that |
| 0:48.1 | relates to that retirement phase of life. If you're looking for the by the numbers episodes, then look for the episodes |
| 0:55.5 | titled By the Numbers where we dive into the more financially related content as it relates |
| 1:00.2 | to your retirement. And of course, we bring you world-class guest week in and week out. So listen |
| 1:06.3 | up. Today, we're going to be covering an article from our weekend reading email that went out this past Friday. |
| 1:12.7 | That is an email that hits your inbox every Friday. |
| 1:15.0 | And it includes four articles on trending topics curated by myself, includes summaries, takeaways, |
| 1:21.2 | and you receive all kinds of other great resources as a subscriber as well. |
| 1:25.6 | Go ahead and sign up by texting us the key letters, W.R. to 888-599-4491. |
| 1:32.1 | We will get you signed up. |
| 1:33.9 | And you can receive the other three articles that we're not going to be covering today. |
| 1:37.3 | We're going to be covering an article from Morningstar titled, You Can Beat the Stock Market by avoiding its worst days, but you won't. And I am going to |
| 1:47.3 | cover this content today with my good friend, fellow certified financial planner practitioner, |
| 1:52.4 | Marshall Johnson. Hey, hey, good buddy. What's going on? Hey, well, it looks like we're talking numbers |
| 1:57.2 | today. One of my favorite things to do. I know you saw me pulling out the good old spreadsheet trying to dim the lights around here. So I'm pretty excited to get into this as I think |
| 2:06.8 | there's some strong relationship here between this article and what retirees are trying to accomplish. |
... |
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