51. It's Time, Babe: How to Know When to Leave Your Job artwork

51. It's Time, Babe: How to Know When to Leave Your Job

At Work with The Ready

June 29, 2026

Everyone tells you leaving a job is a math problem: runway, comp, the next offer, the spreadsheet that finally tips. But most people who ask "how do I know when it's time?" have already answered the question. They just haven't let themselves hear it yet.
Speakers: Rodney Evans, Sam Spurlin
**Rodney Evans** (0:00)
I have a lot of conversations with people who are like, how do I know when it's time to leave? I sort of am of the mindset that like, if you're asking that question, you already know you're leaving. Like you've already made that. If you're asking me, how do I know it's time? It's time, babe.
Hey everyone, this is At Work with The Ready, a podcast about work design and how organizations can make change work in their favor. I'm Rodney Evans and I am here with my friend and co-host, Sam Spurlin.

**Sam Spurlin** (0:35)
Friend and co-host, I thought we got a promotion.

**Rodney Evans** (0:37)
You did.

**Sam Spurlin** (0:39)
Great, thank you.
Companies, they're facing more change than they were built for. The problem is that organizations are still running on management ideas from a completely different era. Rodney and I work with leaders and teams who are redesigning how work actually gets done. So change becomes fuel in the tank instead of sand in the gears.

**Rodney Evans** (0:58)
On this show, we share patterns that we're seeing inside of organizations and what we think is working and what we think is getting in the way. Today, we are going to talk about leaving jobs because there is ever so much in the news about job displacement and it's frothy out there. But first, we got to check in because how you do something is very important and it matters and you should do check-in rounds. Sam, what is today's question?

**Sam Spurlin** (1:27)
Our very important and deep check-in question today is, Rodney, in what way or ways are you super basic?

**Rodney Evans** (1:35)
I mean, in what ways am I not super basic? The thing that comes to mind that has like become such a brand of mine that I have so much merch because you know, people know that you love something and they just keep buying you things of that thing, is Miller Lite.

**Sam Spurlin** (1:52)
You do know that.

**Rodney Evans** (1:53)
Oh yeah, that's true. I've been drinking Miller Lite since I was 14

**Sam Spurlin** (1:59)
What number are you about to throw out here?

**Rodney Evans** (2:01)
Since I was 14
It didn't become a beer of choice until I was older. I think it's the perfect beer. And I have, like people buy me t-shirts and hats. Ali bought me a mini cooler of a Miller Lite can to fill up my glass of Miller Lite. I know it's basic, but I also just think sometimes things are basic because they're perfect.

**Sam Spurlin** (2:23)
Yeah, because they're good. And why deviate?

**Rodney Evans** (2:26)
Why mess with it? Yeah, I don't want to eat an IPA. That's disgusting.

**Sam Spurlin** (2:32)
All right, well, let's not have other delicious beers catch strays here.

**Rodney Evans** (2:39)
Sam, in what way or ways are you super basic?

**Sam Spurlin** (2:43)
I mean, also in many ways, what comes to mind for me right now is that I will not look down my nose at a chain restaurant. I'll go to an Applebee's, go to Chili's. You kidding me?

**Rodney Evans** (2:55)
Hell yeah.

**Sam Spurlin** (2:56)
I will unironically search out a subway from time to time. I don't care. Come at me. I think they're great.

**Rodney Evans** (3:03)
Dude, Footlong Subway Club, no notes.

**Sam Spurlin** (3:05)
Yeah.

**Rodney Evans** (3:06)
Yeah.

**Sam Spurlin** (3:06)
I'm a cold cut combo Footlong Italian earthen cheese.

**Rodney Evans** (3:09)
They're my second favorite. They're related.
Today, we are talking about leaving jobs. The reason I propose that we do this episode, Sam, is twofold. A lot of anti-work rhetoric right now in response or as backlash to job displacement and job elimination that is both real and just being justified by CEOs as being AI related. There's a lot of this doomsday stuff. There's a lot of this early retirement, like fire sub-community action happening. Then also, you and I are both experiencing role changes and both presumably put a lot of thought into them.

**Sam Spurlin** (3:49)
Yes.

**Rodney Evans** (3:50)
Fingers crossed. I thought it could just be fun to talk about both the sort of sky level shit, but also the very midnight zony part of making job change, because it's an incredibly big transition in people's lives.
Cool.

**Sam Spurlin** (4:08)
Yeah, I love that. Let's dig into it. I feel like an initial tee-up, just to say out loud, is we're obviously not talking about getting laid off, which is a different type of losing your job, which might be very top of mind for a lot of folks, especially if you're working in tech right now.

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