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Ready For Retirement

Retiring at 54: Why Darren Says It Feels Surreal | Retirement Reality

Ready For Retirement

James Conole, CFP®

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

5706 Ratings

🗓️ 12 November 2025

⏱️ 31 minutes

🧾️ Download transcript

Summary

In this episode of Retirement Reality, Darren shares what it’s really like to walk away from work at 54 and why it still feels surreal. After decades of saving, hitting his number, and paying off the house, a company reorg gave him the push he needed to finally make the leap. He talks about how it feels to go from structure to freedom overnight, what surprised him about early retirement, and why he refuses to see it as a “forever” decision. For Darren, this season isn’t about stopping life —...

Transcript

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0:00.0

Let's assume your last day of work was on a Friday.

0:02.0

You have the weekend, we've always had weekends.

0:04.0

There's nothing different about that, but Monday rolls around.

0:06.0

The first Monday of no work. What did you do? One thing I always like, I would walk into work, and when I'd walk to work, I always, if it was a beautiful day out, I'd be like, I just want to keep walking. I want to like spend the day exploring and like going out and do things. So I think in that first week, I did a lot of walking.

0:23.8

And during the day, you know, like, I would walk around outside with like a huge,

0:25.1

like a dumb smile on my face.

0:36.8

I was like just so happy and like couldn't believe that like this is basically what I'm going to be doing. I'm just going to like whenever I want. I can just go out, walk around, go anywhere, do anything. For decades, retirement was just a theoretical number until one day it wasn't.

0:59.1

Darren hit his target retirement number, he paid off his mortgage, and then he waited for the right moment, a company reorg that opened up a window for him to retire. Eight months later, he's in phase one, walks on Tuesday afternoons, health first, and a life full of small joys. But what's interesting about Darren is he's proof that you don't need a grand passion just to get started. In today's episode, we dig into health care worries, solo trips when friends aren't free during the week, and a very helpful reframing of the word retirement in the

1:03.7

first place. Enjoy today's episode with Darren. Darren, thank you for joining me on today's episode

1:09.3

of retirement reality. I would love to hear from you.

1:12.1

If you could describe your retirement in just one word, what would that be?

1:16.8

Yeah, I guess I would probably say it's kind of surreal.

1:21.5

Yeah, I find it very, very like, after all these years of planning, just surreal.

1:27.3

They'll be able to actually do it.

1:44.9

Surreal. Okay. How long have you been retired? Eight months. Eight months. So it's still pretty fresh. I'd say I'm in the honeymoon phase. I'm kind of just figuring out how it goes. And so, yeah, yeah. So let's dive into that. You've been retired for eight months. ensure sure, retirement eight months in could look different potentially than retirement three years, and five years, and ten years in,

1:49.1

but surreal. What was surreal about retirement to you? Yeah, I guess, you know, like, you know,

1:56.7

I had worked for 30 years and I had been saving for many of those years for decades.

2:02.6

And kind of over the years, you just kind of watch this number go up and down until they go up.

2:07.6

And it's this theoretical number that you're just kind of looking at for abstract.

2:11.6

I always treated my investments as like I could only put in, I couldn't take out.

2:15.6

So I was like, it was kind of like I didn't touch it once it was there. So I never saw it as a, it was kind of real thing. It was just a number. And yeah, then one day the number says, you don't need to work anymore. And then, you're like, oh, wow, okay, this theoretical money. And that was something that's actually being very tangible and then one day you know when I

2:34.2

finally pulled the trigger then you know then my life is just so completely

...

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