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Early Retirement - Financial Freedom (Investing, Tax Planning, Retirement Strategy, Personal Finance)

Root Talks: How to Get Past the Fear of Retiring Even When You Have Enough

Early Retirement - Financial Freedom (Investing, Tax Planning, Retirement Strategy, Personal Finance)

Ari Taublieb, CFP®, MBA

Real Estate Investing, Stock Investing, Careers, Save On Taxes, Retirement, Business, Personal Finance, Investing, How To Retire, Early Retirement, Retirement Planning, Entrepreneurship

4.7583 Ratings

🗓️ 3 April 2025

⏱️ 21 minutes

🧾️ Download transcript

Summary

You've run the numbers. You have enough saved. Your spreadsheet says you can retire comfortably. So why can't you pull the trigger and leave your high-stress, high-paying job behind? This struggle represents one of retirement planning's most challenging psychological hurdles. After spending decades accumulating wealth and building a career identity, many successful professionals find themselves paralyzed when the time comes to actually step away—even when financially prepared to do so. Our ...

Transcript

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0:00.0

All right, you and I know there's a big difference between being financially ready to retire and actually being ready to retire, which, of course, extends beyond just financial.

0:09.8

And that's what we're going to talk about today.

0:11.0

We actually have a comment from someone in the root collective, which is asking that exact question of, look, I've run the numbers, I'm ready to go, I have enough, but I can't bring myself to not just

0:22.8

leave my job, but leave my high stress job that also happens to be very high paying. And this is a

0:29.5

predicament we see time and time and time again of we work all our lives thinking that as soon as

0:35.3

we have enough money, we're going to call it quits,

0:43.1

we finally get there, and it becomes very difficult to actually pull the trigger and call it quits.

0:47.2

Will you read for us the question, not the question, but the comment that's in the root collective?

0:52.0

I will. And for those who do not know what the root collective is, it is our free community.

0:55.7

So you can go join this and see exactly what we're looking at under the tab that we call the what I wish I knew earlier. And this comes from D.T. Lyons, who says,

1:01.9

taking the big leap, curious to hear from others that have stepped away from high stress, high paying

1:07.1

career and retired early, but continue to work doing something they're passionate about

1:12.0

at the fraction of the salary.

1:13.6

I'm in that situation.

1:14.8

My analysis says I can do it, but it's hard to take the leap.

1:18.5

We see this a lot.

1:22.4

And as I just alluded to, the reasons why is it's not just a math problem.

1:26.8

It's not just a spreadsheet problem. There's a lot that goes beyond that. So I'm curious, are you see that question? You see that comment. We've got some really good comments, people responding to that from the collective, which we're also going to point out. Where does your mind go first? Yeah, my mind first goes to, it would be really weird if you were to be like oh my gosh I can retire I have

1:46.3

no worries no political concerns no economic concerns I know exactly what I'm going to do in

1:50.8

retirement that would actually concern me as an advisor because I'd be like look how could you really

1:56.5

know you haven't done it yet so you can ask friends and you can kind of see on some online forums,

2:01.4

even like this root collective and see what people say. But there's always going to be probably

...

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