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Ready For Retirement

The Surprising Regrets of Wealthy Retirees | Root Talks

Ready For Retirement

James Conole, CFP®

Investment Planning, Bonds, Education, Stocks, Cash, Business, Dividend Investing, Retirement Planning, Retirement, Investing, Tax Planning

5706 Ratings

🗓️ 15 May 2025

⏱️ 16 minutes

🧾️ Download transcript

Summary

Retired with millions—but full of regret? In this episode of Root Talks, James and Ari share the real stories no one talks about: wealthy retirees who did everything “right” financially but still feel like they missed out. From sacrificing health and relationships for more savings, to realizing too late that they were planning for someone else’s version of success, these lessons are emotional, practical, and essential. What you’ll learn: Common regrets wealthy retirees confess after leaving...

Transcript

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0:00.0

James, I alluded to this a few weeks ago, but I spoke to a woman, very nice woman, who said,

0:04.9

I'm really upset. I have $3 million. And I said, look, I don't want to be mean here or anything,

0:09.4

but by you saying that, you know, there's a lot of people who would love to have $3 million.

0:13.6

So it's just weird, and I don't hear it every day. Why is it you're mad that you have $3 million? And I said it like that almost a little bit, hey, come on, why are you mad?

0:23.7

You have $3 million.

0:24.4

And she said, you're right.

0:27.0

That's why I'm asking you to explain it.

0:28.4

And she said, the reason I'm upset that I have $3 million is because I found out that I'm not going to be able to hike to the degree that I'd like and I will not be traveling because my sciatica has gotten really bad. I said, okay, that's an interesting response,

0:41.8

sad response. Tell me more on the financial side. And she said, well, I was never doing any

0:47.3

financial planning because my neighbor always had more money than me. And I always just thought I

0:53.4

needed as much money as they had. And they had, I don't remember, four or five million bucks and I always just thought I needed as much money as they had.

0:54.8

And they had, I don't remember, four or five million bucks.

0:56.8

So I just thought I needed what they had, and they were also single.

1:00.4

And so this woman eventually went on to tell me that she has this sciatica, which is essentially a nagging disease that's basically in like your hip or outer leg where

1:12.0

it's constantly just uncomfortable. You're not in like cruciating pain. Some people are, but she was

1:17.3

saying this got really bad from her continuing to sit at work. And she said, I didn't need three

1:23.8

million. I needed about two to two point two million and the last three, four years at work

1:29.4

was when this got really bad. So here I am upset thinking I don't really need this and now I can't

1:35.3

even spend what I have. So the reason that we're transparent on these episodes is because we don't

1:41.1

want you to look back going, well, now I can't do what I want to do because financially I didn't plan well. And the theme of what we're going to be discussing

1:47.7

today are what are some of the biggest lessons that we've learned from our clients. And this was

1:54.8

an actual thread left in the community from someone who says, what has root seen from clients

...

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