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Jill on Money with Jill Schlesinger

When Can I Downsize My Job?

Jill on Money with Jill Schlesinger

Audacy

Investing, Education, Business, Self-improvement

4.61.9K Ratings

🗓️ 15 January 2026

⏱️ 20 minutes

🧾️ Download transcript

Summary

I want to stop working at my current job in the next few years and move into a second act job that is less stressful and more meaningful. Is it doable?

Have a money question? Email us ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠here⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

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Transcript

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0:00.0

Welcome to the Jill on Money show. It's Thursday, January 15th, and we are here answering your financial questions.

0:09.8

If you have one, go to our website, jillonmoney.com, click the contact us button, write us a note.

0:15.9

And if you'd like to join us live, check the box. We would love, love, love to bring you on the air. If you would like,

0:23.0

you can check at all of our free content that lives on the website. We've got another podcast,

0:27.3

which is called Money Watch. We have a blog. We have a radio show. There are videos. There are

0:32.4

resources. And we also have a free weekly newsletter. And you should sign up for that.

0:37.1

Okay, let's get started

0:38.3

today we are talking to paul who joins us from chicago hello paul what's going on hello how are you

0:45.4

jill nice to meet you good to meet you what's going on what can we do you know um i feel very fortunate

0:51.3

um i've been working hard for many many years, and I find myself at a crossroads.

0:58.1

I'm trying to figure out, can I get off the rat race and can I potentially downsize work,

1:05.0

you know, to a sort of second act before finally retiring.

1:09.8

I like it.

1:10.1

So we're looking for a glide path, but not a like, I must get out because I'm miserable,

1:17.3

but like a different trajectory slowing down a little bit because you've saved a bunch of money.

1:23.5

Is that fair?

1:25.0

Yeah.

1:25.6

And the question is, how quickly can that glide path be executed?

1:29.1

Is it 18 months?

1:30.7

Is it five years?

1:32.0

Is it eight years?

1:32.9

That kind of thing.

...

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