anything goes with emma chamberlain - knowing when to quit

Episode Date: March 5, 2026

[video available on spotify] you always hear people say "don't quit! persevere! the only way you fail is if you quit!" and you never hear people say "it's okay to quit. sometimes quitting is a necessary step on the path to accomplishing your ultimate goals." so in today's episode, i thought we could dissect the complicated dilemma of when to quit. when is quitting the move, and when is it the move to persevere? Save Your Way, exclusively at Hotels.com. Visit www.squarespace.com/EMMA to save 10% off your first purchase of a website. Learn more about your ad choices. Visit podcastchoices.com/adchoices

You always hear people say, don't quit. Don't give up. You got this. Persevere. The only way you fail is if you quit. So don't quit. And you never hear people saying, you know, it's okay to quit. Sometimes quitting is a necessary step in accomplishing your ultimate goals in life. Sometimes quitting is the bravest thing you can do. You never hear people saying that because it's not as sexy. There's something, easy and sexy about don't quit. And we've been hearing it our whole lives, or maybe I should just speak for myself, but I've been hearing that my whole life on Nike t-shirts, in little storybooks for kids, don't quit. I feel like I grew up thinking that quitting was a negative thing, was a bad thing. And that definitely stuck with me. Even though now I'm an adult who has the ability to sort of shade in these ideas that I absorbed as a child. There's a weird thing that happens when you absorb something as a child. Even when you get older and you have the ability to color things in and sort of look at things with a more nuanced perspective, these beliefs

that were sort of cemented into the brain as a kid sort of remain there subconsciously, even if you know better. And that's how I feel about. quitting. Like, I know that the advice don't quit does not just apply to everything 100% of the time. I know that there can be value in quitting an endeavor. I know that. But because when I was a kid, there was sort of a negative connotation around quitting because a lot of the times quitting isn't the answer, right? Persevering, pushing through is the answer. Because as a kid, I was constantly being told not to quit and that failure only really comes when you quit, I just always felt sort of guilty about quitting, even when in my rational mind I know that quitting can be the bravest

thing that you can do. So in today's episode, I thought we could dissect the complicated dilemma of when to quit. When is quitting the move? And when is it the move to persevere? But I think this episode is going to be more focused on trying to figure out when to quit and how to accept quitting as a necessary part of our journeys, because I feel like that's the more challenging feat. I briefly interrupt this episode to let you know that this episode of Anything Goes is presented by Hotels.com. Save Your Way is a new feature on Hotels.com, and it's as simple as it sounds. When you book a trip as a Hotels.com member, you decide how to use your savings. Take the instant savings now or bank the savings as rewards for later. It's your call, only at

hotels.com. Save your way is available to loyalty members in the U.S. and UK on hotels with member prices. Other terms apply, C-Site for details. Now back to the episode. I mean, listen, sometimes quitting sounds easier. Oftentimes quitting does sound easier. But I think a lot of us feel guilt about it, right? Whereas none of us are feeling guilty about persevering. And maybe I have a unique perspective on this. Like maybe this isn't the universal feeling around quitting. Maybe this is sort of unique to me. I mean, nothing's unique.

But nothing can be unique to me. Like there's no way I'm the only one experiencing this. That's not possible. But I imagine there are some people out there that have the opposite problem. Like perhaps they feel like if things aren't working, then that is a sign to quit and move on. And maybe they actually need to sort of work on

persevering in those moments and potentially taking it as a growth opportunity or utilizing it as a growth. Maybe what I'm saying is maybe some people struggle to persevere when they actually should persevere and they miss out on growth opportunities. Whereas for me, I think I have the tendency to stay in a situation for too long out of guilt of quitting, even when quitting can be a really important step in this journey of life and can actually lead to, you know, to success and fulfillment. It can be a step in that. And I struggle with that reality.

But I do imagine that some sort of struggle with the opposite reality, which is like quitting too easily. And perhaps that's the default sort of approach to deciding whether or not to quit something. And perhaps that's why the advice that we grow up with is don't quit no matter what. Don't quit.

Keep going. Because maybe we're prone to quitting as humans, which makes sense. But I guess I have a tendency to take things too far. I don't know. I think I'm a perfectionist. So maybe it's a little bit of that going on. But regardless of where you fall on the spectrum, regardless of if you're somebody who tends to quit too easily,

or you're somebody who could work on a perspective shift about quitting, seeing that it's not necessarily always a failure, I think it's safe to say that the decision of whether or not to quit something is a challenging one. I don't think it matters where you are on that spectrum. I think it is always a challenging decision, especially in a certain category of dilemmas and situations in life. In fact, I think it'd be useful if I defined the types of situations that are so challenging to figure out. okay, because there are certain things that you definitely shouldn't quit, and there are certain things that you definitely should quit, and it's obvious, okay? You definitely should quit anything

that's toxic, bad, unhealthy, detrimental to your well-being, like, that's obvious, right? Any sort of bad habits, any sort of toxic environments or situations, obviously you should quit that. That's obvious. And not always, and I'm not saying that to insult people. who are struggling to quit something that is perhaps toxic or bad for you because it's not easy, okay? I mean, it can be easy. It also can be really challenging. So I'm not saying, oh, that's obvious. You know, and if you don't see that that's obvious, fuck you. That's not what I'm saying. I'm saying coming to the conclusion that you need to quit those types of things is easier. The process of quitting is still going to be challenging in a lot of these types of scenarios. But I think

the answer is usually pretty obvious to the person. It might be scary. It might be uncomfortable. It might be challenging. But I think it's more obvious. And same thing goes for like an overarching goal in life, right? Like if your goal in life is I want to be fulfilled in my career. If the goal in life is I want to find love, you know, whatever. If you have a big goal like that, you should never give up on those goals, you know, those sort of overarching. life goals that are abstract and could come to fruition in any way. Those goals we should never give up on, right? Those, we should never quit in the pursuit of those goals, right? The types of situations I'm talking about today are much more complex, more specific, more isolated situations or

dilemmas where the answer's abstract. There's no right or wrong answer. These situations or dilemmas are a jumbled mix of positive and negative that make coming to a conclusion of whether or not to quit more challenging. Like these situations are neither super positive or super negative. Or maybe they are kind of positive or kind of negative, but it's not obvious. Do you know what I'm saying? Like the answer is not obvious. Let me give you some examples. I think. that'll help paint the picture. This episode is brought to you by Uber 1. Uber 1 for students is the best way to save money on Uber and Uber Eats.

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A great example would be whether or not to quit your job, when your job is okay, you kind of like it. And, you know, maybe financially it's comfortable. But maybe you have bigger dreams. You're like, ah, this is not ultimately the career I want to be in for the rest of my life, right? But also it's comfortable. And maybe like maybe this could turn into. a career. Like maybe I could climb the ladder and this could become a really fulfilling career for me.

But also it might not. That's a great example. Another example, shutting down a business. If you're an entrepreneur, the dilemma will arise at some point of whether or not to continue the business unless you have some sort of miraculously genius business plan that is foolproof. and from day one you never take a wrong step, which probably happens to some people, but not, not many. Entrepreneurial ventures are ripe with challenges. You know, on one hand, a lot of really successful entrepreneurs failed like 20 times before they had their successful business. You know, you hear stories time and time again about entrepreneurs who started all these different businesses and then failed. But then they got back up and they started a new one, you know? And a lot of times

when you hear that story, it's like, well, I had to know when to give up on one venture and start a new one, right? But then you also hear stories about entrepreneurs who started a business and it hit rock bottom and they hit bankruptcy and then they got back up and then they kept pushing because the founder believed in the business. You know what I mean? It's a tricky one. In a moment of challenge in a business, Do you persevere? Do you let it hit rock bottom and pick it back up? Or do you let it go and start something else? That's another example. Another example would be moving back to your hometown. Maybe you move to a big city and that was sort of your dream for a period of time. But perhaps moving to the big city isn't what you thought it would be. Maybe it's more lonely.

Maybe the opportunities that have arose aren't actually as fulfilling as you expected them to be. Maybe you're feeling homesick. Well, this could be a huge opportunity for growth, pushing through that discomfort and finding comfort in this unfamiliar place, finding fulfillment in this place where fulfillment isn't coming as easily as maybe you thought could be an incredible growth opportunity. It could also be that you had expectations about this situation and they didn't end up living up. And the reality just simply isn't what you want.

You could quit and move home or you could persevereignty. year. Another example of this kind of dilemma. Last example, a mediocre relationship, romantic relationship specifically, because I feel like friendship, friendship's different, right? Because you can have a bunch of different friends. And you can have a bunch of different levels of closeness with your friends. Whereas if you're somebody who practices monogamy, you can only date one person at a time in a serious way. And so there's more pressure on that one relationship and it's more important that you check certain boxes, right? Whereas in friendship, you can have a funny friend and then you can have like a super supportive friend and then you can have a party friend and then you can have a shy, nostalgic

friend from your childhood. Like you can have all these different types of friends that check different boxes in different ways. Whereas with a romantic relationship, it's more important that you check certain boxes, right? Because you can't check those boxes with other people unless you're polyamorous in which you can. But a decent portion of us are not. So I think this really applies with romantic relationships, particularly mediocre ones, one where it's like, let's say you're in a relationship and it's good. You know, it's okay. There's a decent sort of companionship. There's a good amount of potential, but it's maybe not amazing, right? You love them, but maybe you're not really sure if you're in love with them.

But at the same time, like, it's good. It's not bad. It's not toxic. It's not necessarily unhealthy. But maybe it's not electric. Well, that happens in relationships sometimes, you know? Like, the reality of romantic relationships is that it's not always going to be this, like, explosive, obsessive sort of situation.

In fact, sometimes that's actually not a good thing because that's like a sign of almost a state of sort of delusion in a way. I would, that's my opinion. That can be sort of an unhealthy dynamic, actually. But we love that dynamic because it's so exciting and so fun. So perhaps the relationship is just in a lull. And it's actually a really beautiful relationship. It's just not super exciting in this moment.

And it's worth staying and blooming in the relationship because, you know, it actually does have a lot of potential and it's just having a normal low point. Or maybe it's just not right. Maybe it's just not your person. although actually I should be careful with that type of verbiage, verbiage, because I don't know if that exists. Your person, does that exist? Up for debate. Up for debate.

And I think there's a lot of smart people out there that would say, no, who are much smarter than me. So I should probably trust them. But that's a dilemma. You know, what do you do? Do you stay in it? Do you leave? What do you do? I think for me, my baseline, right?

as I said earlier, is to stay in it, to keep pushing, not to quit, because I don't want to fail. No one wants to fail, you know, that's, that's, no one wants to fail. And I also don't want to miss out on a growth opportunity, right? So oftentimes my default is like, okay, I'm going to, I'm going to stay in it. I'm going to keep pushing. And I think that that can be the right approach and I think it can also be the wrong approach. But it's really, really hard to tell which. let's discuss the pros and cons of quitting. Just like what good can come from quitting and what good can come from persevering.

Which should we start with? Let's actually start with the value of persevering, not quitting. I briefly interrupt this episode to let you know that this episode is brought to you by Squarespace. Squarespace gives you everything you need to showcase your business and get paid with customizable sites, professional invoices, online payments, and built-in scheduling and email tools, plus their design systems let you easily create a website

that really captures your brand. Go to Squarespace.com slash Emma for a free trial, and when you're ready to launch, use offer code Emma to save 10% on your first purchase of a website or domain. Now back to the episode. What's the value in sticking with it? Number one, growth. Because I think the trickiest part of this dilemma

is that we grow when we persevere through challenging situations. You know, when pursuing a goal, working in a particular career, starting a business, moving to a big city or moving out of your hometown to pursue something, being in a romantic relationship. We do these things because they're usually like goals that we have, right? Like we want to have a certain type of career. we want to be in love. You know, those are goals that we have.

And the pursuit of those goals inevitably will bring challenges inevitably. And persevering through those challenges is how we grow. If we buckle and we quit every time there's a challenge, we don't grow. There can be so much value in persevering because the only way to get through the challenge is to grow. The only way out is through. And I think the drive from the goal is what pushes us to overcome the challenge in the situation. And then we come out the other side of better person.

You know, that's sort of the beautiful thing about having goals and working towards them is that not only are we working towards a goal that could be potentially very fulfilling in our lives, but also the journey is sprinkled with beautiful growth opportunities. and I think anything worthwhile is going to challenge us and force us to grow as people. Okay, moving on, there's often less regret if you fully see things through. When you don't quit,

you're never left with the haunting thought, what could have been? You know, like, what if I had stuck with it a little longer, what could have happened? You know, you almost never regret persevering. That's not actually necessarily true, though. That's not necessarily true. You definitely can regret,

persevereing. But we're not going to talk about that yet because we're talking about the value of persevering right now. So we'll save that for later. You can regret persevering, but I will say, at least in my experience, I'm less likely to regret persevering because that what if can really haunt a person. And lastly, I would say persevering helps us get into a practice of getting up after we fail and or pushing through a challenge instead of automatically quitting. Like practice makes perfect, right? And the more you persevere when things get tough, the more that will become a practice in your life, and the better you'll get at it. You know what I mean? And I think that that's a really great way to live. Like I don't give up when shit gets tough. I push through and I see it through.

practice makes perfect. And so I think the more you do it, the better you get at it, the less discouraged you get when things go wrong, you know, and I think that's a really beautiful thing. But let's get into the value of quitting. Sometimes we have to make space for the next venture in our lives. You know, the saying, close one door to open another. I don't know if that's the saying. What is the saying? It's like you've got to close one door to open another, to open a new one. Whatever. You get the idea. You've heard that before. Your grandma's probably said it to you, your mom, your uncle, okay, your friend. You've heard it. And it's very true. I think particularly in relationships, you know,

you really got to close a door to open another one a lot of times. If you're still hung up on, well, if you're still hung up on a relationship or you're still in a relationship, you can't be opening another door, right? But I think this also applies too in career as well. If you're putting all of your energy into one sort of path career-wise, it's very challenging and sometimes impossible to see what's out there, explore other options unless you let that go. You know what I mean? We only have so much time and energy,

and it's our responsibility to use it wisely. And if something is really not working, it's okay to say, you know what? I think the wisest move right now is to let this thing go, quit, and pursue something else. And you know what? Worst case scenario, if I go and pursue something else and I was wrong and I let a good thing go, there's always an opportunity to return back to that thing. I mean, it might not work.

Like, you might not be able to get your old job back. You might not be able to go back to your ex. But you could at least try. It's our responsibility to say, okay, the situation. isn't terribly bad, but I think it's preventing me from reaching my highest, fullest potential. And I know that being in this situation is preventing me from exploring that. And I need to explore that. Next, in the same way that practicing perseverance can be incredibly valuable, I also think the practice of knowing when to quit something is also really valuable. See, that's why it's tricky. It's like,

I think both skills are really important. And so I think there's value. in looking at a situation and saying, you know what, I think that there's more for me out there. I'm going to quit this and try something else. There's also a lot of value in that. And I think the beautiful learning from that is becoming comfortable with this sort of feeling of failure. Because I think we've all been taught over the years that quitting is the ultimate form of failure. And quitting in some ways it's failure. But it's failure on a small scale, right? If you quit something, that doesn't mean you're a failure in your life. It just means one little thing failed. And that's okay. That might be a crucial step in your journey to ultimate success.

As I said earlier, there are so many stories of entrepreneurs who started 10 businesses and failed at all of them before they started their 11th, and that was the one that succeeded. And I think getting comfortable with failure is a challenging but really valuable thing to do, because they think a lot of times, in order to ultimately succeed, sometimes you have to let things go completely and completely quit. Another value in getting comfortable with quitting

is quitting can be really discouraging, right? And when you quit something completely, you're like, I'm done with this. It takes a lot of strength to start something new again, right? But I think that experience can be not only, really productive and ultimately be a step in reaching your ultimate goals. But I also think, too, it teaches you resilience. It's a growth opportunity as well. There's growth in deciding to quit as well. In the same way that there's growth in perseverance, there's also growth in quitting. It's just a

different type of growth. But both opportunities can invite growth. And last but not least, I think the value of quitting can be the time. Now, I don't, I'm, I'm like nervous to say this because I don't know if it's the right way to look at quitting. Like, I think this sort of mentality can get toxic. So I'm going to be careful about how I say it. But also I'm just going to say it. You can waste a lot of time in a situation that's not ultimately pushing you to become the best person you can be and reach your ultimate goals. You can waste a lot of time in situations like that. But I also don't think time's ever wasted. Everything is a lesson. So that's why I'm hesitant because I'm like, it might just be part of your journey to be in a situation for too long, probably, that is not maybe serving you.

Like, that might be a part of your journey. So I'm like hesitant to say that, not quitting could cause you to waste your time. I think it's kind of a dangerous statement, and maybe I shouldn't be saying it, but I think quitting can sometimes save you time in a way. Like, you know, if you're in a mediocre relationship, quitting that relationship and being like, you know what, this is not, I think there's more out there for me.

Now you have more time to find who's next. Do you know what I mean? But then at the same time, it's sort of toxic because that there is no time, there's no specific timeline. There's no right or wrong timeline. So maybe I don't stand by that one. So how do you figure it out? How do you figure out what to do?

You're in a situation where you're not sure whether you want to persevere or quit and let it go. How do you figure it out? Well, over the years, I've gathered some questions that I ask myself when I'm in this dilemma. And I'm going to share those with you all. And that's not to say that I have it all figured out, okay? but this is what in the past has helped me.

And it was actually really helpful to write these down in a way because I feel like I've had these questions sort of floating around in my head, but I've never written them down. And I'm copy and pasting these questions and putting them in a document titled, should I quit or not or something? And I'm going to return to these moving forward and go down the list. Okay, I might even journal about these things, right? Like these might make their way into the, the journal because I think that having them all written down as sort of like a questionnaire

could be really helpful for me moving forward. But these are the questions that I ask myself. Number one, is this situation challenging me to grow or preventing me from growing? Okay. Is this situation uncomfortable in the only way I could get through it is by becoming a better version of myself in one way or another? Or is this situation just completely stagnant and there's no room to grow? It's just not a good situation or it's just not a great situation. It's just almost kind of like a neutral bleh situation where there's no push to be better. It's just kind of bleh. Do you know what I'm saying? Okay, next question number two. Am I persevering in this situation because there's potential here? Or because

because I'm stuck in the belief that quitting is bad and I'm afraid of failure. Like, am I just in this for the ego? Am I just in this to prove a point to someone or to myself? Or am I persevering here because there's genuinely potential? Next, question number three. How much damage is this situation doing to me in my life? And what is the likelihood that it will get better and be worth it? Get rational with it.

What's the data? What's the data showing here? Is this ultimately doing more harm than good? And it can be sometimes hard to tell in these sorts of situations that are sort of jumbled messes of positive and negative where it's not obviously bad or obviously good. It's just kind of both. Sometimes you have to really dig in and analyze to see where it's leaning. Is it leaning more positive or is it leaning more negative? And what's the likelihood of it going in a positive direction and what's the likelihood of it going in a negative direction? And what's the likelihood of a miracle

and is that worth the risk? You know, if it's like, most likely it's going to go bad, but it could go good if there's a miracle. Well, that's not something to ignore. Miracles do happen, you know, and that's valid. You're not completely, you know, kooky for giving that a chance or believing that that's possible, but how down bad will you be if the miracle doesn't happen?

And it ends up going in a negative direction. Next question. Number four, is there something else I could be putting my energy towards that would be more fulfilling? Is this situation getting in the way of me progressing in my life? Like, is this particular situation so consuming that there's no way to explore options outside of it while within it? Do I have this sort of innate feeling that there's more out there for me and that I'm not pursuing it? because I'm in this, I'm kind of complacent in this sort of situation. Next question. Am I ready to make a decision? Have I tried everything? Are there any rocks left

unturned? Will I regret not giving it more time? Have I given it enough thought in analysis? Am I jumping to conclusions? I think a lot of times when it comes to these types of situations, really marinating on it is the move. Jumping to conclusions based on emotion, is not the move, you know? Really taking the time to let the decision process and waiting until you're as certain as you think you can possibly be, I think is the move. And last but not least, how much damage will quitting cause? Am I in a place where I can reasonably leave this situation right now and it won't cause serious issues? Sometimes you might want to quit something, but you're like, I actually literally can't. And that's okay too. You know, quitting.

can sometimes be a journey, right? It can be a process. It doesn't need to be this boom, night and day, now I was doing this thing, and now I'm not anymore. You know, sometimes it's a process. Let's say you, obviously, like you don't have another job lined up. You can't just quit your job. Or let's say you live with your partner. You can't just leave the relationship. You live with your partner. It's like a weird, you know, sometimes it's a process. And you never want to be, you know, too irrational and sort of irresponsible with these with these sorts of things that's not good you want to be prepared and make sure you set yourself up properly to quit i'm trying to think if there are any other questions i ask myself that i didn't mention no i think that's it it's so hard it's so hard and you know

i'm i'm actually in a place in my life right now where particularly in my career i'm trying to figure out the next five years of what I do with my time. And I've been deeply analyzing, you know, what to continue pursuing and what to let go of. And it's been an incredibly uncomfortable journey. I'm really struggling with it, to be honest. And that is why I'm making this episode. That's why this episode is relevant, because I'm trying to figure that out. And I'm looking at every single facet of my career and asking myself all of these questions. questions. And it's a journey. I'm taking my time. But let me tell you, it's driving me nuts. It's driving me nuts. And it's scary. And it's scary. And it's weird. But I'm like, fuck, I think I'm

ready for the next kind of version of my career. And some stuff's got to go. Like, I might have to quit some stuff. Or maybe I have to, maybe not. Maybe I need to evolve things. Like, it's a whole dilemma. And so I'm really deep in it right now. But this episode was really helpful for me, honestly, because it was sort of healing to discuss the value of quitting certain things at times because I'm somebody who's prone to persevering. And I think there might be certain things in my career right now where I'm like, I actually think this is preventing me from my next wave of God knows what. But also it might just, but also maybe not. I don't know. Anyway, I'm going to go reflect on these questions that I just gave you all of what to ask yourself when you're faced with a dilemma like this.

I'm actually going to go really journal on these things. So I got to go. But thank you all for listening and hanging out. Hopefully this episode was enjoyable to you in one way or another. If you enjoyed it, new episodes every Thursday. Anything Goes is on the internet everywhere all over in various places at anything goes. I'm on the internet at Emma Chamberlain and my coffee company. is Chamberlain coffee. I love you all. I appreciate you all. Hopefully this episode was

coherent, honestly, because I just got over the flu and my brain is not working. It's not working well. It's like foggy, foggy fog up there right now. I mean, I don't even know how I just talk to you all for this long because my brain is not working. Also, if you heard weird sounds coming from my throat, it's because I have mucus in my throat and my chest is like making weird mucus sounds. So hopefully that didn't gross you out. Okay, I love you all. I appreciate you all. I'll talk to you in a week. Bye.