Is This the Worst Time to Retire? 3 Ways to Prepare (Just in Case)
Big Picture Retirement®
Devin Carroll
4.7 • 545 Ratings
🗓️ 10 November 2025
⏱️ 31 minutes
🧾️ Download transcript
Summary
Everyone's wondering if this is the worst time to retire. With high valuations, stubborn inflation, and constant uncertainty, it's easy to feel uneasy about your timing. In this episode, we look at what history teaches from past "lost decades," why the order of returns matters, and how to protect your plan without panic.
You'll learn three ways to prepare just in case: build a spending bucket, stress-test your plan, and rethink your risk exposure. Retirement success isn't about timing the market. It's about preparation and peace of mind.
Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their individual firms.
📍Contact Devin's team at https://carrolladvisory.co/podcast1
📍Contact John's team at https://www.rossandshoalmire.com/
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Transcript
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| 0:00.0 | The Big Picture Retirement Show does not provide tax, legal, or financial advice. |
| 0:04.3 | Listeners are encouraged to seek out their own advisors in these areas. |
| 0:11.0 | Everyone, welcome to the Big Picture Retirement Show. |
| 0:13.7 | I'm your host, Devin, joined by my co-host, John Ross. |
| 0:18.4 | I got off my cadence there a little bit, I noticed. John, I screwed that up. |
| 0:22.0 | You think we should redo the opening? Nah. Just let it go? I'll give them the howdy anyway. Howdy. All right. Good. So, John, I ran across an article the other day. I was in between meetings, and I think I was, I don't know, market-wide or somewhere. And I came across this article that said, is this the worst time to retire? It's kind of a scary article. Retirement is kind of what we do. So I decided I need to read this article and see what people are saying. A good clickbait fear-inducing headline. Well, you know, most headlines are fear-inducing, right? They have figured out that Fear sells better than anything. As it always has. And it's going to make you click. |
| 0:57.2 | And once you click, are fear-inducing, right? They have figured out that fear sales better than anything. |
| 0:54.4 | As it always has. And it's going to make you click. And once you click, you're going to get some |
| 0:59.2 | ad served to you, maybe some affiliate offers. You might. And you never know what'll come of that. |
| 1:04.0 | Anyway, so this article went into looking at where we are in the market now, comparing that going back to the 1970s, |
| 1:15.4 | and it gave a couple of tips, you know, to retiring well. |
| 1:21.4 | And it was just all kind of meh type of vice, right? |
| 1:25.3 | Just very generic. |
| 1:26.7 | Surface level, yeah. did it did make me start |
| 1:31.5 | thinking about this is a concern that a lot of retirees have you know to set this up properly if you look at |
| 1:38.0 | where we are in the market now a lot of people are holding their breath this can't last you know the |
| 1:41.9 | market's setting new highs it It seems like every week. |
| 1:45.0 | And it has been. Yeah. And if you look at a lot of the traditional measurements of valuation in the market, |
| 1:51.1 | you know, there's there's three that people are talking a lot about right now. There's the, |
| 1:55.8 | the Schiller, price to earnings ratio, which is the Cape Index. There is the just forward-looking PE that a lot of people use, the price to earnings ratio, which is the CAPE index. There is the just forward-looking PE |
| 2:02.6 | that a lot of people use, the price to earnings ratio on its own that's based on the forward |
| 2:06.7 | earnings. And then there's the Buffett indicator that's Warren Buffett's indicate. And that was |
... |
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