Knowing When to Quit | Lindsay Crouse

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26:21You browse profiles, review past work, and hire with confidence. There's no full-time commitment required. Post your job for free right now at Upwork.com. That's U-P-W-O-R-K.com. Go post your job. The key part in all of this is doing it before you start, because so many of us will start a project and then the goalposts shift. And all of a sudden it's like, I said 100 emails I had to collect or 100 customers, but I'm at 50 and I think it's only three more weeks. So realistically, those emotions, once we're doing something, will often leave us stuck doing it well past the point of no return. And then we're on that slippery slope of sunk cost fallacy.

27:07And telling ourselves, I think, you know, it's time to quit. One way that you know it's time is if you just find yourself saying just one more, just one more try, just one more, just one more thing. And you start lowering those expectations. And it's just you're just rationalizing with yourself. And instead, it's just really time to stop. The other part of this that is not really discussed and certainly not shared early on in our journey and when we are in school or thinking about our careers is just the seasonality of things and how there will be periods where you are directionless and that's okay, but we need to have some tools to actually face that instead of just leaning in on our perseverance or grit in those moments.

27:50Just normalizing that a little bit more is something that culturally we need to do and also something that we need to be willing to do with ourselves. I think there's a lot of 40-somethings. I was one of them who realized at some point we've been locked into, in some ways, locking ourselves into decisions and behaviors and patterns that were made and set by 20-year-olds, like our 20-year-old selves. and we're not changing in part because of consistency. And so you have to cut the cord in some cases in order to figure out different ways of living that might suit you better in the stage of life that you're in.

28:32And that can involve a period of wandering. I did talk to a number of people who were very, very clear with me talking from the other side of quitting, I guess, that quitting will give you freedom. And that's really important as a first step, But it doesn't provide direction. It does not tell you what to do next. And I think that a lot of people can wind up feeling a little lost if they haven't tested the waters and built themselves a little bit of an off ramp. I think it's really important if you are thinking about actually quitting something really important, if it's your job or getting divorced or, I don't know, giving up a goal that you've held for a really long time.

29:11Those are just a few examples. I think you really need to think about what is it going to be like on the first day of not doing this thing? And I think you can imagine that. Wake up and just imagine, I'm not doing, I know I don't want to do this thing anymore, but what would my day be like if I actually wasn't? And I think if you can't answer that question, you need to do a little bit more thinking first to help prepare yourself for a little bit of that wandering. And the judgment that you might face, not only from other people, but also from yourself. What also comes rushing in then is after a few days of maybe having that time back or getting more rest now, taking care of yourself, if you've been facing burnout, and that's one of the reasons that you finally ended up quitting, is then after that, there is that period of, I don't even know what to do because that's just what I've been doing.

29:56it was easier to stay the course because as monotonous as it was and challenging as it was, there were no choices. It was just do the same thing the next day and just keep banging your head at it. Then when you do quit, you are directionless and there is no map of what the next thing is. And that can be really hard for many of us who are so goal oriented and have found so much pleasure in climbing the ladder, whether it's through school, whether it's through work, having that next rung ironed out and in front of us that we can just work towards. Whereas now we're talking about veering off the path and feeling lost and what that will be like.

30:30It's important to remember that for a lot of people, climbing that ladder actually is very appealing. And that's fine. I think you just really need to be honest with yourself about what you're doing and why. I think the one thing that you don't want to do is say, I hate my job, I hate my job, and just keep climbing that ladder out of, again, this passive approach that you're saying. But if you just own it and you say, look, I may not love my job, but I am doing it for the salary and for, I don't know, whatever it is that you're doing it for. The structure, the feeling of belonging, the importance, like the fact that I actually do like my colleagues.

31:07All of those are really, those are fine reasons as long as they're reasons that you're aware of and that you own as opposed to just pretending that someday I'm going to quit and then failing to actually invest in the life that you have. I will say one concept that was particularly resonant for me in the course of writing this book that I don't think I'd really thought about enough in my own life was this idea of it's what they say in Jungian psychology, it's called the provisional life. And this feeling that everything we're doing right now is just a dress rehearsal for that day when our real lives will come and everything will come together.

31:42And that's when it's all going to work out. And so for now, we can just, as you said, climb the ladder, tread water, because it's all going to come together. And I just think that's so devastating, because, again, if you just, if failing to quit means choosing to continue, you're failing to decide and just bouncing these decisions to our five or 10 years older selves to the point where maybe someday it actually is too late to quit. And you're leaving them with the same hard questions about why am I doing this? Do I want to do this? But even greater stakes, because it doesn't get easier to leave.

32:16We just get older. Problem is the stories we share are exactly that. The stories where it did all come together for someone. Our heroes, the people we look up to where, okay, all of that made sense because then they created the iPod or they launched this new incredible unicorn venture that made sense with all these skills. So we can often then ascribe that to ourselves and be like, OK, I don't have it all together here. But once it happens, once it clicks, this will all be worth it. And as you said, you can stay on a path that you should have quit a while ago. I think it's also important to remember that if you're on a time-worn path, climbing a ladder, that rarely leads to discovering the iPod, for example.

32:57Like what that leads to is a stable career that, you know, in a job and something that's pretty steady and that's fine, but it's not going to get you that reckless, risky breakthrough, most likely that I think you'd probably be mistaken to hope that it might. What it's getting you again is that stable salary and a steady career that you might want. However, as a million headlines are telling us right now, those stable paths are shrinking quite a bit and we are going through a lot of upheaval. So I think clinging to those and in that way, it makes sense to cling to those things. But if you're clinging to it out of this hope that by staying in this job, it will always be there.

33:40I would say that's a little misguided at this point. I hope hopefully you're staying in the job also because you like it a little bit or like it like what it's getting you. All right, real talk. What are you paying for wireless right now? Whatever it is, I guarantee you're overpaying. That's the game these big carriers play. They hook you in with a deal and then the bill quietly climbs every few months. Mint Mobile doesn't do that. All of their plans right now are$15 a month, even unlimited. $15 high-speed data, unlimited talk and text on the T-Mobile 5G network. And you don't even have to give up your phone or number.

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34:56See mittmobile.com. Here's something we learned building the art of charm. You cannot be the expert at everything. We found marketing support and dev talent on Upwork. Things we were not experts at, taken off our blade by people who are. We've shipped projects faster, gotten more traffic to our website, and even freed up our time for the work that only we can do. That's what Upwork does. It connects you with specialists, software development, marketing, design, AI implementation, whatever your business needs. Over 170 ,000 freelancers with five-star ratings. You browse profiles, review past work, and hire with confidence.

35:40There's no full-time commitment required. Post your job for free right now at Upwork.com. That's U-P-W-O-R-K.com. Go post your job. It brings up another phenomenon that I'd love to maybe put some of our audience sort of the magnifying glass around, and that's the concept of sliding versus deciding. because there are these small micro movements that we're making, these mini commitments that move us in a direction that may feel insignificant, but can also tie us to a path that we feel like we then can't quit and we're not even conscious of it or not even really aware of it as it's happening. This is why I think the people in their 20, it goes with that observation that you had around how quitting is sort of stage of life.

36:25It's relevant what stage of life you're in in terms of how much you should quit. But if you're spending your 20s, understandably wanting to feel like you've launched, that you've established yourself, like I know I felt that pressure. Many 20-somethings do for a million reasons. You are, you know, you start dating someone and then you move in with them. And then soon it becomes not just when are we hanging out this weekend, but like what are we doing? At some point, you're not going to want to break up and then there's one thing to do but get married. and it's this idea that sliding that continuing like that is a decision too and so something doesn't feel right at the beginning you're actually just bouncing these harder decisions with more investment to again that five year or ten years older self and it's going to be even harder for the fat person to extricate themselves from from these choices that you made when you were young so I think 20 something should quit a lot more than than they're taught to believe But quit intentionally.

37:26Quit so that you're intentionally rejecting one thing that doesn't work with the intention of finding something better that does. And by quitting those things that aren't working, hopefully you are finding something worth staying in. In my own experience, quitting came with a lot of family pressure. So I was in graduate school. I knew at that point that I didn't want to be doing that. I started this media career and podcasting on the side, and it became this fun hobby that just consumed me. And then I made the decision to quit, but my family was not ready for that decision. They thought that I was leaving something very secure and something that they saw successful for something that they thought was frivolous in my 20s.

38:07And I think that's a phase in your 20s that many of our listeners have faced or maybe are facing right now where it's like you feel like you should quit, but your family, your loved ones feel like you're giving up that certainty. You're giving up that path that they think will lead you to success. When we contemplate quitting, we're really easily paralyzed by fear. And obviously, this is our brain protecting us. We naturally hate uncertainty. But usually this quitting, this fear that we have around quitting, it involves this fear of judgment that we made the wrong choice. And I think often this fear proves unfounded.

38:41Studies would say this. So as you were saying, we fear the critiques of others, like our family, the people that are really close to us. There's this bias called the spotlight effect that observes that we often think of ourselves as going about our lives with an imaginary spotlight where we assume that other people are paying a lot more attention to us than they actually are. For the book, I talked to an actress who quit her career after she noticed that all the other actors around her were putting their lives truly on hold for a dream that A, wasn't working, their careers were not taking off.

39:13But it was also a dream that they didn't even necessarily believe in anymore. but it was all because as she told me they told everyone in their tiny hometown that they were going to be a star and they just couldn't let go of that and obviously she felt this pressure too but it turned out that when she finally she did walk away from acting and when she told everyone that she was doing this they actually just thought the same thing as when she set out for Hollywood years ago sounds great we support you and the truth is people rarely care about anything as much as we care about ourselves. It can almost be disappointing to realize this, but no one cares, or at least no one else cares.

39:51Especially in the long term. Yeah, I think in the immediate, it feels like that. But over the long haul, like looking back now, almost 20 years later, my family doesn't even think about that decision. But in the moment, it can feel that catastrophic if you make the wrong one, like your life depends on it. And that in our own internal raising the stakes makes that fear feel more amplified. That's because we don't just fear judgment from other people. And in that case, your parents are probably actually in some ways supporting you, right? They are being the devil's advocate. You clearly wanted to leave and they're helping to make sure that you're not just doing that frivolously.

40:28And I think that's actually constructive and caring of them because you did leave anyway. So it's not like they actually stopped you. And then, but I think you're onto something else there where it's like, we're not just fearing all the judgment from other people, but the worst judge of all is ourselves. And I think we wonder, and this is what your parents were hopefully helping you to figure out, but it's like, what if we regret that decision to leave? But this often also winds up feeling a little unfounded. Research shows that over the long course of our lives, we tend to regret inaction more than action.

41:00And quitting is an action. It's a bold action. And hard as it is, it's a choice. and it may mean sucking it up and taking the loss. You are walking away from grad school. That's a big deal and you should treat it like that. But at the same time, you are also opening yourself up to new opportunities and because you had to let go of the path that you were on in order to find that better thing. And so it can, again, I think it's just making that decision and owning it. In the long run, we're likely to be happy with the choices that we made. I wanna talk a little bit about this statement you had in the book.

41:36because I think many in our audience might feel like, okay, I don't want to be seen as lazy. If I'm not working, I'm lazy. So instead they just focus on grinding indiscriminately. Everything's got to be a grind because the last thing I want to do is be lazy. But you argue that actually that is also a form of laziness, just viewing everything as I have to keep grinding. You're not making an active choice. You're not asking yourself why. You're not owning it. I think this idea that I can't quit is often something, it's often, I think that telling ourselves I can't quit is often a lie that we wish were true.

42:15Because it then helps us not even have to think about, again, that choice. It's a little more timid than. And lets you off the hook. Yeah, exactly. And to somebody like that, I would say, well, have you actually run those numbers? Have you actually thought about other alternatives? And I think it's important to actually do those, ask yourself those questions because you may wind up staying. I do not think that everyone should quit anything, that everyone should quit everything. I think you should quit some things much more readily and easily than we tell ourselves. But if you haven't even asked yourselves the practical questions around quitting but are constantly saying that you want to but can't, you are letting yourself down for sure.

42:58Let's talk about the ghost ship because I found myself doing this recently before reading the book and researching for the show. I just was curious, like, what did the cancer lab that I left continue working on after I left and thought a little bit about what if I didn't make that quit and that move, what would my career have been if I just stayed in cancer research? And I think for many of us who are similar age or older, we have those ghost ships, those decisions we made. And we think about the alternative reality, the butterfly effect of what if it went the other way? Yeah, this is a beautiful quote by Cheryl Strayed, the writer, where it was from a column that she wrote for Dear Sugar, her advice column.

43:37And it's just always stuck with me where she says, somebody was writing to her asking about whether or not to have children. And she just wrote, once you make your decision, this is the ghost ship of the life that you didn't live, of the path that you didn't take. And there's nothing to do but wave to it from the shore. And I just thought that was such a beautiful idea that when we're younger, all of these different branches of our lives stretch out before us. And if you're someone like me and you're ambitious and someone like you, you want to take all of them. You want to do everything. It's like life is there for the taking.

44:18And that's such an exciting idea. And it can almost be disappointing. This is like we're saying no comes in. If you don't say no, you can actually take everything for a while. and it can just be really hard to not look back and regret and second guess yourself and I just love this idea that these are that those are lives that we didn't that we didn't live they are paths that we didn't take they are the ghost ship and they we our houses may be haunted by them but they're not real they didn't exist and you just have to let go of them there's this philosopher named L.A. Paul, who she starts her book with a similar concept where she says, imagine that you're a vampire or imagine that you're that you have the choice to become a vampire.

45:01In fact, check me on exactly what the exact phraseology is. But I love what she writes about there because she says that you she walks you through this thought process of how to make this choice. But she says that you cannot know how you're going to feel about it afterwards, Because if you become a vampire, you are fundamentally a different being than the person who you were when you were making this choice. And so how you view that choice in hindsight will be a different person or a different being that assesses that choice once the choice is made. And this obviously is very applicable also to choices around do I have kids or not.

45:37You think if you're going to have kids, your life will just stay the same, which probably isn't true because it's going to change anyway. But if as a parent looking back on the question of should I have kids, you can't actually judge that past choice anymore because you've changed. You're a parent. You have kids now. And I just thought that was such an interesting idea that the choices that we make will change the being who is judging them in hindsight. And you have to let go. There's a lot of skeptical audience members who up until this point listening are like, that all sounds great if I want to be entrepreneurial or make choices that my family might be unaccepting of.

46:13But I got to explain this to recruiters. I am on a career path where quitting has stakes. And if I have this on my resume or I have this result that I have to explain away in the next job interview or to the recruiter, that's going to have stakes for me that I can't quite surmount. So what do you say to them who feel that pressure from those external people who will be taking a pretty critical look at their quitting? It depends on the nature of how you quit. I think we often think about quitting as just one blunt seismic action where one day we've had it at work and we scream that we're done in a rage.

46:46And I don't think you should do that. I don't think that is what you want to explain. That's not the case you're making. No, no, that is impulsive. That is not a strategic way to quit. And it's rarely the healthiest way to cut the cord. Instead, I would test the waters and wade in slowly. And maybe you're not trying to become an entrepreneur. But I think if you're strategic about figuring out what you want to do next, I think that's very easy and thoughtful to explain to recruiters. And it can often be a great way to figure out what's next. If you take this testing the waters approach, you can do that even from the job that you're in.

47:25I don't think you even need to leave your job to do that. You can explore from the perch of your job, I think. And then that also helps you get away from this kind of I can't quit attitude because it actually medicates some of the risk. There's a really good example that I loved of the R &B legend Bill Withers. And he's a really interesting example because he was born in, I guess he wasn't talking to a recruiter, but he was born in poverty and had to take whatever jobs were available to him to support himself. And he wound up landing a job in L.A. manufacturing toilet seats for airplanes. But at the same time, he started playing guitar in clubs and exploring new interests.

48:05And I think in some ways he was just doing that because he wanted to meet women. But eventually he discovered that he was incredibly talented and he kept his factory job the whole time. Even as his breakthroughs were hitting the charts, he hedged his bets and he kept making toilet seats. And I just and he actually had to get laid off in order to leave that job because he was just so risk averse. But by the time that happened, he was on Johnny Carson in 1971 and he was ready to embrace his new career. And so by then he not only had sort of the gift, but he had the confidence. And I think that's what you need to talk to the recruiter.

48:36You need to be able to convince the recruiter that you have the foundation to succeed, whether or not that's on your own terms. But you just want to have a reason why you left. And again, this whole conversation has been about how quitting is a decision, quitting is bold, quitting is a risk. These are things that should be very attractive in job assets in your career, not drawbacks. But you just need to be able to be thoughtful about how you articulate them and how you lift them. The narrative piece is the important component here of recognizing that you didn't quit because you were forced out or because you had a terrible boss, but because you made a clear decision, you saw that as the next step or next path to you, unlocking new experience, getting a new skill, giving you a chance to write something, create a substack, launch something, and then come back to that career.

49:23But that narrative piece, you have to be constructing as you're thinking about quitting after you're quitting. And then as you lead yourself into that next conversation around what the next move is versus, well, I just threw my hands up and I had to. I couldn't take it anymore, which probably isn't going to go over well in a job interview scenario. Just showing intentionality and thoughtfulness and strategy about your career generally is wise. And that can involve quitting or not quitting. But either way, again, you should have reasons for why you're doing these things as opposed to just sort of that passive that was in front of me.

49:58I was grinding. I was working hard, especially the older you get, the less effective and compelling those qualities themselves will be. If you're listening to this and you feel very similarly, like it's all perseverance, I can't possibly quit. Quitting is not in my vocabulary. Let's talk about micro quitting. How can we start to introduce this concept in maybe lower stakes ways that our audience can start to strengthen that muscle to be more decisive in these bigger moments? There's micro and there's macro quitting. Micro quitting would be paring back little things in your life, eliminating the clutter.

50:33Macro quitting, obviously, is quitting your job, like getting a divorce, breaking up, like truly. Yeah, like truly making, truly like picking a different path in your life or at least aborting the path that you're on. And those are different things. But I think if you have a problem in your life, there's a lot of research that shows we rarely want to, we're often inclined to want to add things to this problem. There's a study where people were given this tower and they were trying to get the tower to stay intact. And everybody wanted to add something to the tower. But the truth, but the solution lay in subtracting and taking a piece away.

51:13And I think there's a really interesting analogy to micro quitting in our lives there where subtracting can actually. But when we have a problem in our life, we often want to add more, like whether it's a hack or a routine or a diet or I don't know, whatever. Add more miles, add another workout. start cold plunging. But often the answer is in taking something away, like maybe just going to bed at a regular time. And so in order to do that, micro quitting can really be helpful. It's eliminating the clutter from your life so that you can focus and prioritize what does matter and what you do want to keep.

51:50And so I found, yeah, for myself that micro quitting was really valuable because I especially just accumulate things. I started to realize I'm like, oh my God, I'm a mental hoarder here, like in terms of the lifestyle that I'm living. Even look at my inbox. Like, why am I still on listservs from 20 years ago in college? And so I just started going through this stuff and like saying no, which is another word for deleting. And I think if you do go through these exercises, it's liberating because you realize your life isn't just fine. It's often better without those things. And I think just going through that exercise can help you to look at other parts of your life that you may want to or need to change.

52:29What I found so fascinating about that is sometimes we don't even recognize that we're just holding on to things. Maybe you said that old set of golf clubs that you just keep around. So you're like, well, I'll get back to golfing. And we both know you won't, but we just can't seem to quit it. So having that opportunity to trim some of these things in our life that we're just holding on to because we're afraid of quitting in the first place. It's just another example of learning that saying yes is not the only way to live a full and happy and satisfied and productive life. It's also saying no. Well, thank you so much for joining me today.

53:03Where can our audience find out about the book? You can get it wherever you get your books, Amazon, Barnes & Noble, your local bookstore. And it's out on September 8th. And you can find me, I guess I'm mostly on Instagram these days, at Lindsay Kress. Thank you so much for joining. Absolutely. Thanks for having me.

53:47We'll see you next time. and roasted bacon Brussels side. The season's most desirable menu has returned to Sweetgreen, featuring fall's best dressed. Make your move. Order on the Sweetgreen app. This episode is brought to you by ChatGPT. Hey, it's Bill Simmons from the Bill Simmons Podcast. Have you guys heard about ChatGPT work? It's the new way to use ChatGPT for bigger multi-step projects. And when you need more than just answers, give ChatGPT work access to your apps and files and it can create real work documents like spreadsheets, slides, and structured reports. Get started at chatgpt.com by selecting work mode available on Plus and Pro plans.