Why Are We Still Not Quitting? – Why Are We Still Doing That?
No Vacation Required
The Power of Quitting: Breaking Free from the "Stick With It" Trap
Why do we treat quitting as a dirty word? From cultural programming that labels quitters as "losers" to the identity shame that keeps us stuck in toxic environments, we tackle the deep-seated stigma around walking away. We explore why we stay in situations way past their expiration dates – whether it’s a job, a relationship, or even a book club – and how to reclaim quitting as an act of self-trust and alignment.
Drawing on personal stories of navigating layoffs and hostile work environments, we break down the "sunk cost" mindset and the social pressures that keep us small. Learn how to build your "quitting muscles" through micro-quits, how to support others in their transitions, and why staying unhappy is never a noble sacrifice.
Onward and Inward,
SUPPORT NO VACATION REQUIRED:
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CHAPTERS:
(00:00) The cultural stigma of quitting
(00:25) Mind Share: Cozy season in Seattle and the silence of Taylor Swift
(05:52) Navigating layoffs and the vulnerability of the workforce
(09:52) A story of standing your ground at work
(12:12) Refusing to play by the old rules
(14:45) Logistics, sunk costs, and the "good girl" myth
(19:08) Practicing micro-quits and body signals
(23:06) Validating clarity over groupthink
(25:42) Why staying unhappy isn't noble
(26:44) Worth the Time: Breaking up with identities and expectations
KEY TAKEAWAYS:
Staying Unhappy is Not Noble: Many of us were raised to believe that enduring misery is a sign of character, but sacrificing your well-being for a situation that doesn't serve you is not a virtue.
The Sunk Cost Fallacy: Putting time and energy into something is not a legitimate reason to stay if the situation has become unhealthy or stagnant.
Practice "Micro-Quits": Build your confidence by opting out of small obligations that drain you—declining an invitation or leaving a party early—to prepare for the bigger life shifts.
Growth vs. Depletion: Learn to distinguish between the healthy discomfort that leads to personal growth and the soul-crushing misery that leads to total depletion.
RESOURCES MENTIONED:
YouFinder Personality and Strengths Assessment
Book: All the Cool Girls Get Fired by Emily Tisch Sussman and Tiana Lowe
Practice: Body Signal Check-in (Identifying dread, exhaustion, or resentment)
FULL TRANSCRIPT:
Caanan
Today we're taking on something that is fundamental to a no vacation required life, but that makes people squirm a little. Something that triggers deep cultural programming, collective pearl clutching, and at least one relative who will whisper, but what will people think? Today we're talking about quitting.
Kent
So mindshare, what's been on each of our minds? this week. And I'm going to go like micro mini mind share. And I'm going to say what's been on my mind is cozy season. And I'm fully here. I'm fully here for cozy season. We don't get brutal winters here in Seattle at all. It's pretty moderate, but it's still fire and candle. And comfort food meal and premium TV, premium movie, good quality work session season. And I am here for it.
Caanan
I love cozy season. I love the term. It's like a marketing term. Like holiday or something you'd hear in a retail store. Like it's cozy season.
Kent
Yes. What's on your mind, Canaan?
Caanan
Well, it's funny you bring up cozy season because what's on my mind came up today for you and I when we were on a very wet, but ultimately very cozy run.
Kent
Yeah, I was going to say, wait, hold on, let's reframe that. We were on a very cozy run.
Caanan
Yeah. Around the peninsula we live on here in Seattle. And It's something I actually kind of reluctantly bring up because I really hate hot takes. You and I are not hot takes, guys.
Kent
No, because everybody has the same hot take and posts it and acts like everybody else isn't posting it.
Caanan
Oh my God. Yeah.
Kent
Okay.
Caanan
We get into it. But it's, you know, all this stuff that's going on with ICE and the raids and the detentions and the, you know, the whole like, Nazi-ishness of it all has got us, in some kind of way. So there's no hot take there. It's terrible, flat out. But I read this thing in the Guardian that mimics something you and I had talked about.
Kent
Yeah, the Guardian article, yep.
Caanan
And it's that ICE used Taylor Swift's songs in some of their TikTok videos or something. We won't even get into the fact that ICE is on TikTok or whatever. But there has been a weird silence from Taylor and her team on this. And it's kind of bizarre because she's, you know, she will make fun of herself for her team's litigiousness around the use of her music. And so the silence around her music being used by ICE has got me wondering what the hell is going on with Taylor?
Kent
The Guardian, who we trust, is on this beat. And we're like, yeah, so if this billionaire isn't speaking out about a misuse of property, like what's going on? And yeah, I don't think you're hitting the full panic button yet, but it's just a weird thing in our time. Like now ICE is using stars music illegally. It's just the weirdest.
Caanan
Oh, and I just want to make it clear, like, you know, we're bona fide Swifties and we can show the receipts. But, you know, something is a little fishy and we don't know the whole story and we may never know the whole story, but it feels weird to me. And so I'm just throwing it out there. It's been on my mind.
Kent
So yeah, I'm so excited about this one. Why are we not quitting? Why are we still not quitting? We are huge advocates for quitting. And kind of a funny story in the kind of the last iteration of our work, working with companies and people, much to everybody's surprise. Well, I guess even when we were in the traditional workforce, we were always big fans of quitting, of telling people to quit, would make people very kind of uncomfortable. But we had some turning points that made us have a certain degree of comfort around this that we're going to get into. But in a way, we wanted to acknowledge that this is sort of a continuation from an episode we did recently about loyalty, specifically Why are we still being loyal? So it kind of starts with that. Like there's loyalty and this leads you to not want to quit. And here we are today talking about why are we still not quitting?
Caanan
Well, I have some, I actually wrote down some bullet points about why people aren't quitting and why this whole topic triggers people. And I'm just going to run through them because we'll get into this deeper. but I want to hit on these. And then you have a great story around this that I want to talk about.
Kent
I love it. You're going to pull out the, I'm an expert. So listen to these bullets. This is your domain. Go.
Caanan
Yeah. So why quitting triggers people. We've got the whole cultural conditioning of it all. You know, the quitters are losers. Never give up. stick with it no matter what, all of that. We've got the whole identity shame thing, which is people don't quit because quitting means they're flawed and not the situation they were in.
Kent
Yeah.
Caanan
We've got the whole fear of judgment, as I said in the opening, what will people think?
Kent
Huge.
Caanan
And then there's that really terrible with crabs in a barrel behavior where the second you look like you're getting out of something, people want to drag you back into it because they feel terrible about themselves if you break free. So there's four pretty good reasons why people don't quit.
Kent
We can talk about each of those four things.
Caanan
Absolutely. But now that I've kind of laid that groundwork, I do want to hear, I want you to tell this story.
Kent
Yeah, a little more context about why in our NBR trajectory of it all, why this very topic is a big one for us. Again, very connected to the work we've done. But I'd say it's very origin story aligned. people are like, wait, no vacation required. How did this all come about? What does it mean? All that. Being in the traditional workforce, as we both were, we saw some things. We have been through some things. We saw some things people shouldn't see. Yeah, no, but it's kind of true. Like, I went into the job that I'm going to talk about in a second, having not long before time escapes me, being part of a layoff. My entire team, the team I was on was laid off in the tech world of the time. And I was younger, you and I were new in relationship. I was younger, all that just feels so fragile. And I hated that feeling. And in this bizarre twist, I think I've talked about this on the podcast before, where, at the time, of course, like these things weren't done over e-mail as they are now or over Zoom, where I was working, somebody at least two steps above you, your boss couldn't be the one to lay you off. So I was in a pretty high position. The person 2 steps above me was a vice president and they had to fly in. We were living in Portland at the time. They had to fly in to lay me off. And it was kind of like a regional director type thing. So he was flying around to all the desks, all the regions over a couple of days to terminate people. But there's this weird thing, like I've got an 8 o'clock tomorrow with a VP who's flying to lay me off. But it just felt so vulnerable and so weird and started great conversations between us. So it was one of those pivotal things in my trajectory, our trajectory, who we are like, I am never letting this happen again. I'm never going to be in a position where I'm not seeing the signs that my team is going to be laid off and I'm going to have to sit there while some ding-dong reads from a script, it was just, I mean, humiliating, even though, you said the societal stuff, humiliating, my entire team was being let go.
Caanan
It had nothing to do with you or your performance. It still feels humiliating. It's a totally valid feeling.
Kent
Okay, so the plot thickens. This is where it gets even better, where I use that kind of experience, we use that in our couplehood to make better decisions going forward. So fast forward, I'm a really top manager at another company, so top that they pull me aside and say that a guy who had been terminated for some kind of assault It was ruled that he was wrongfully terminated and they were putting him on my team. And I was new. I was kind of a new superstar, blah, blah, blah, blah, blah. So that was kind of weird. Like, wait, I'm new. I don't even know what's going on. And you're putting somebody who this very contentious, terrible situation. So I have to keep fast forwarding because this is not about this single experience. But So a miracle happens. I, he works for me. So I develop a relationship with him, turn his performance around.
Caanan
Not a miracle, because you're just extremely good at your job. I'm saying that. Go ahead.
Kent
Yeah. And all of a sudden, long story short, from the hires up, he's like, oh no, this isn't good. You were supposed to manage him out. Right, and I'm not going to feign naivety here. Like, I know this is how it goes, of course, at companies. But I was just like, no way. You drop this bomb on me as a new leader in this company. I have to put all this time and energy into this person. I actually, beyond all chance, make it work. And then I'm in trouble. because I didn't get the unwritten message that I was supposed to manage him out. Right. So I was like, well, okay, that's too bad. But this happened. I mean, there's nothing we're going to do now. he's doing well. What are we going to do? But they weren't done yet. And I think they got to the point where they were talking about saying, if this doesn't change, you're going to be on a verbal warning. And I was like, no way. This does not end well. So yeah, through many conversations together, I was like, no, I'm getting out of there. I'm not starting on this road because I'm not all of a sudden going to dismantle everything I've done with this guy. I'm not going to completely shift gears on him, who's actually stepped up and did what he needed to do. I am not going to be that person. Thankfully, we're in a situation where, you know, we could make this work. But I made the decision, the writing's on the wall. I get rid of this guy. or I'm in trouble. And I was like, I don't like this job that much. Keep in mind, this was a minute ago when, I think leaving your job now is a much, much tougher decision. I still think more people need to do it, blah, blah, blah, blah, blah. But then you could reasonably expect, you know, something else would come along before anything too crazy happens. Yeah, so we just made the mutual decision and it was pretty easy based on what had happened in our lives prior, like the experience I had, some experiences Canaan had, and it was like, no. And I remember there were a lot of nerves around that because they were like, wait, you're what? They kind of wanted to do takes backsies because I was really promising there to begin with. Then this bizarre thing happened, though. I quit. I give notice. And they're like, okay, great. In these couple of weeks, you've got to do the reviews for your team.
Caanan
This is my favorite part of this story.
Kent
Yeah. And I was like, wait, hold on. I get it. You know, as I said in my letter, smooth transition, but review season doesn't start for like four more weeks. So we're not even too review time. That needs to be the next person. They'll have my healthy notes and everything. It was like, nope, you need to, you need to do the reviews before you leave. And I was like, I'm not doing the reviews before I leave. So it was just like empowerment central. And I completely had them blown away. They didn't think for a second. that I would quit.
Caanan
They couldn't wrap their brains around it. No. Never mind, this is for a different conversation, but they were also pretty homophobic, which was not unusual at the time. There's that. But that's a whole different story. So as I said in the last segment, there are lots of reasons why quitting triggers people. And there are a lot of reasons why people stay in situations that are unhealthy or that no longer serve them. And it's not just quitting jobs, although you talk about that because it's a big thing. It's a huge thing for people and it's happening all the time. It's very relevant.
Kent
Yeah, when you say quitting, it's the anchor that people have. I mean, it's the first thing. people think of. And that's a shame too, because, you quit, you quit other things. I think of how we recently, or I guess it's not so recent, but we left Substack. There's a whole podcast about that. You can listen to that whole story. And speaking of quitting and Substack, I think of like, people's weird notions around quitting. Back to what you said in the intro. Glennon Doyle, I think over the summer, makes the big decision to come to Substack. She gets there. People tell her, oh, you did it all wrong. You weren't humble enough. She's like, this is exactly why I didn't want to come to this place. I'm leaving. And then She gets all of this, oh, now you're a quitter and you left wrong. And why did you only last two days? Just all this judgment. We could scope up and make this about more than quitting. Make it about just the judgment everybody has on every single thing everybody does. But we're talking about quitting. So we use that, her quitting. Substack is like, this is so great. It's great to see people who have a lot of attention on them quitting and talking about it. in real time.
Caanan
Yeah, I love the Glennon Doyle example because it's not actually unlike what you experienced in the story you just told where a situation becomes unhealthy or hostile. It doesn't work for you anymore. It doesn't matter if it's like terrible, it just doesn't serve you. And then you quit. And the people that sort of participated in creating the hostile environment or making it unpleasant look at you like, what are you doing? You're not allowed to walk away from this abuse or this hostility. That's not part of the social construct. And so as I said in the last segment, there are lots of reasons, that being one of them, the social construct around quitting, white people stay in situations way past their expiration dates. But I want to talk about some of the other reasons people stay stuck. And one of them is obviously, especially when it comes to work, logistics, right? It's hard to leave a job if you need the money or you need the healthcare or you have a lack of alternatives. And so we want to recognize that, makes it difficult. And that's a legitimate reason why you may not be able to quit. It's not a legitimate reason for not being in a, I'm going to get myself out of this situation mindset, but not everybody can just up and quit. We want to get that right out. But there's also things that are completely in your control, like the whole sunk costs thing, like I'm not going to quit because I put so much time into this. That is not a legitimate barrier to leaving something, right? That's just a mental construct and it's a bad one at that. So there's one, if you find yourself thinking like, I can't get out of this because I've already put so much time into it, that whole sunk cost mindset is a terrible place to be. But then just these like, these myths around loyalty and the whole social pressure around staying in things that are unhealthy, right? Especially for women, like you're supposed to be the good girl or you're supposed to do the right thing and stay in something that doesn't serve you.
Kent
Yeah, with that, I'm thinking too, like the avoidance of discomfort, like the uncertainty can be unbearable for people. in so many facets, relationships, jobs, clubs, think of that, anything, going to the same grocery store. It's like they know me there. I don't want to start and learn a new thing so that the facing uncertainty, like having to explain yourself, the disappointing others, if I don't keep going to book club, that's going to bring it down to 9 people. And I don't want to be that person. So it's really strange. And you've outlined so many great examples of the things we will prioritize over what we need.
Caanan
Amen.
Kent
Okay, so where does this leave us? How do we get more comfortable with quitting.
Caanan
Because there are lots of reasons why it's difficult to quit.
Kent
We get that. Yeah. So we talk about building your quitting muscles. We talk a lot about interrogating, questioning that internal script that so many of us were raised with. And you ask, like, why do I believe that quitting is equated with failing. Who told me that quitting makes me a failure?
Caanan
Yeah.
Kent
So you're doing that work, but you're also doing things like practicing micro quits. You're opting out of obligations that drain you. You're declining invitations. And as we record this, we're getting into the season of obligations. Try declining some of them. You're leaving early. This is a big one for us. being big runners and loving to get out into nature. If things go too late, we're often leaving early, but it's this strange thing like you're ruining it by leaving early. We're like, no, we got to do what's best for us. Another one I really like from our toolkit is paying attention to your body signals. We're so big on that lately. Those responses, are you feeling dread? Are you feeling exhaustion? Are you feeling resentment? These things aren't worth it. Because remember, as I said in the last segment, you're prioritizing that over the right thing for you. Just think about that. Think finally about the difference between discomfort that leads to growth and misery that leads to depletion.
Caanan
Oh, I love that. Wait, hold on. Discomfort that leads to growth. And what?
Kent
And misery that leads to depletion. We're always urging our clients, what's on the other side? I know you don't want to say the thing or write the e-mail or send the text or do the run. or try the vegetarian or whatever. But we're always saying like, imagine you're on the other side. Is it going to feel better than this misery that you're carrying? Because you sent the text, you've done the thing, you're playing along, you're being nice, you're being the good girl of the good boy. So really weigh that out.
Caanan
That's great. And we talked about earlier about how much pain we feel because the social construct, because we feel so much pressure to not quit or to stay stuck. And so I want to talk about how we can be more supportive of people who are quitting, because I think this is really important. We change our own behaviors, but we also start to shift the societal pressures that create the discomfort in the 1st place. So we're talking about things like when people around you are quitting or contemplating quitting, validate their clarity instead of doing the whole, why would you do that?
Kent
Yeah.
Caanan
It's so simple. Just validate them.
Kent
We talked about this recently. Like just, I'm so happy you're drinking green tea. I'm so happy that makes you happy. We don't have to have a big conversation about what changed in your life. Why are you drinking green tea?
Caanan
Yes.
Kent
Yeah.
Caanan
And also like that, goes to my next point, which is, you know, their quitting isn't about you. And this is what we had, the conversation we had in that podcast, that this isn't a time for you to project your own insecurities and fears on them. Just validate their choices. and then celebrate their alignment with their values. And this is something that you need to do with yourself as well. Like reframe quitting as choosing values and then celebrate the alignment with your values. Another great thing you can do to support somebody who's quitting is just ask, how can I support this transition for you? What a nice bit of grace that is.
Kent
And that applies to so many things. Because oftentimes, we're so conditioned not to talk about these things. It's that you're noticing a shift or a little bit of depression or a little more silence or a little more removing themselves from the group. So you're asking the question like, hey, what do you need right now?
Caanan
Yeah.
Kent
Then they're like, I'm thinking of quitting my job.
Caanan
Yeah.
Kent
I just need somebody to talk to or whatever.
Caanan
Yeah. And then just like, big picture going up to like 30,000 feet here. Just resist joining the crowd that shames people back into bad situations or suffering or things that are no longer serve them.
Kent
Otherwise known as groupthink.
Caanan
Exactly. Yeah. Just be supportive. I guess that's sort of the TLDR, be supportive. But actually, I want you to TLDR this whole thing because we put a lot of points out there.
Kent
Oh, yeah. Well, I wrote down before we started some kind of what I think are the big takeaways. So #1, staying unhappy is not noble.
Caanan
Oh, I'm giving like drag queen claps for that.
Kent
Yeah, I'm going to go back and yak all over again. Because this just touches on so much of what we've already said, but it's those like, this is what you do. This is what we do as a family. This is what a good person does. This is what a college graduate does. All that stuff. So staying unhappy is not noble. Number 2, your life is too short for obligations that shrink you. Period.
Caanan
Period.
Kent
Discernment. Your life is too short for obligations that shrink you. And #3, you're allowed to leave situations that don't serve you, and there's no apology required. So even though I know what's worth the time this week, I'm going to ask you, what's worth the time.
Caanan
Well, we've got a book that is so perfectly aligned with what we've been talking about today that I want to recommend it. It's not like we're not going to take this book to the grave with us. But I mean, we're not going to be buried with this book. We're obviously not going to take it to the grave.
Kent
It's a strong recommendation, not a very strong recommendation.
Caanan
Yes, it's a four-star reco, but it's a reco nonetheless. So the book is called All the Cool Girls Get Fired by Emily Tisch Sussman and Tiana Lowe. dosher. I hope I said those names right. Anyway, we're recommending it because it's so perfectly aligned with what we're talking about. And it's pretty funny. It's tender. It's a really good look at how breaking up with jobs and identities and expectations that no longer fit, how difficult that is. And what I think the book does especially well is crack open the shame and the guilt that so many of us carry around quitting, all the things we just talked about.
Kent
Well, in this case, specifically around getting fired, but it's very much the same thing. Like, yeah.
Caanan
It absolutely is. And it's these stories that we tell ourselves and society tells us about failure and loyalty. And I said in the earlier, especially for women, this idea of being good. So I like that this book like we said, it's not our favorite, but it gives really good permission to release things that are no longer healthy and see quitting as an act of self-trust. And so it's a solid reco.
Kent
Yeah, I mean, and I love it because anything that dismantles, and even from kind of powerful voices, anything that dismantles the shame around getting fired or quitting as if it's this personal failure gets major thumbs up from Team Kent and Kane. But to add a little more context to why this is a recommend and not a super strong recommend, the stories in the book come from people who have a lot of flexibility and privilege. And it's hard not to, you know, it's easy for you to say that as you're reading through. Because these people have safety nets and options, it's a bit of a different experience than an everyday person who's facing these things. But a recommended read nonetheless.