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Ready For Retirement

Ready to Retire? Here's How to Tell Your Company │ 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

🗓️ 29 May 2025

⏱️ 25 minutes

🧾️ Download transcript

Summary

In this episode, Ari and James explore the emotional and practical sides of retiring—specifically, how to have the conversation that officially ends your career. Whether you're months away or years out, this discussion tackles the fear, hesitation, and freedom that come with telling your boss you're done. You'll hear real stories from Root Collective members who’ve taken the leap, insights on counteroffers, and a powerful reframe: every “yes” to more work is a “no” to your time, your family,...

Transcript

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0:00.0

The Root Collective is our free community where you can go and learn from other people

0:04.3

in a similar stage of life to you. It's one thing to hear from James or myself, hey, you should

0:09.0

go retire early. Hey, you should consider this strategy. It's different when someone else is saying,

0:13.4

hey, I'm 54. I want to retire early. It's health care that's bothering me. It's, oh my gosh, how am I going to fulfill my time? But today's episode

0:21.6

is a special one. I alluded to it two weeks ago, but it's about actually how do you quit?

0:27.8

We're talking about logistically, how do I tell my boss or myself, if you're running your own

0:34.1

business, hey, I'm going to walk away. And this was prompted by a post

0:38.4

in the Root Collective, and that is how we select what we're going to talk about. And this comes from

0:42.5

Eric, who says, what was your experience when you told your employer you were retiring? He writes

0:48.1

a lot of awesome stuff here. I'm going to summarize it. And he says here, I'm going to give my employer two months notice so they can find a

0:55.0

replacement. I know they're going to try to talk me out of it. They're going to make promises.

0:58.4

They're going to throw more money. I will certainly be professional and thank them for the opportunity,

1:02.9

but more money is not what I'm looking for. I need to start valuing my time over money. So start

1:09.6

valuing time over money. I don't know how old Eric is, but the first

1:13.3

thing I'm seeing is, was that not happening before? Why now? These are thoughts that go into our heads.

1:18.5

He further goes on to say, I was curious if others here who may have retired experience these

1:24.0

things and how did you deal with it. So that's what we're going to be talking about today. Let's do it. And there's three main categories that I think through. The first is obviously the financial side. Like don't go say you're going to retire if you don't have that dialed in. The big things I look at is do you have income to replace your paycheck? Obviously, the paycheck's going away. Do you have insurance coverage that will see you through and you'll maintain the right health insurance coverage?

1:47.5

Have you made the appropriate changes to your investments? And do you have a tax strategy to

1:51.4

minimize whatever your tax liability might be when you start living off your investment? So that's

1:55.6

obviously step one, but I think Eric, I've got to assume, has gone through those steps. It's more of the,

2:01.8

call it the emotional side or the fear side or what do you do when you feel like you're letting

2:05.1

people downside of this. I got so many thoughts. If people, I was fired for my last job. I was

...

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