Tiger Sisters - Are You Settling in Love or Career — and Don’t Even Know It?

Starting point is 00:00:00 Let's be real. You might be settling right now in your job, in your career, in your relationship, and even in your own potential. And the worst part, you might not even know it. We both have more than once. And today we're going to talk about how to know if you're settling, why high achieving women do it more often than you think and men, and how to get out of it without blowing up your entire life. Settling isn't failure. But staying there once you know better, that is. Yikes. If you're listening to this, it's probably not by accident.

Starting point is 00:00:33 Your gut is trying to tell you something, and we're here to help you listen to it. As always, in this episode, we have a bunch of mini exercises so you can take the learnings and apply them directly to your life. And we also have case studies like we did at Harvard Business School and Stanford GSB. I'm Gene. I'm Sherey. And we're the Tiger Sisters. We are your Wall Street and Silicon Valley Big Sisters.

Starting point is 00:00:56 And we're a top 10. business podcast on Spotify where we talk about money, power, and love. Honestly, I know this episode can be very hard to hear and to listen to. And if you do in your heart of hearts know that you are settling, I empathize with you. It is not an easy feeling to come to terms with. It's actually so uncomfortable and so weird. And so in listening to all of this, we are here with you. But we do have some tough love for you guys. The first thing we're going to talk about is the symptoms of settling. Yeah, I think a lot of times people think settling is something that's like really dramatic and when you're in it, you feel terrible. But it doesn't always feel like straight

Starting point is 00:01:47 misery. Sometimes you just feel fine. Like you're in a job that, you know, is going fine or you're dating someone that looks perfect on paper but it's not actually great or you're shrinking yourself to keep the peace. It's fine. Everything's fine. According to a Harvard Business Review article, 85% of people worldwide feel actively disengaged at work. And that's not just burnout. That's people waking up, going through the motions, and calling it a career. And that's settling. Yeah, I think that's very common for people.

Starting point is 00:02:20 They basically choose something that's comfortable, which is kind of the equivalent of settling, but they don't realize they're kind of killing off their future self. Is that dramatic? Kind of. It's very dramatic. But it's kind of true if you're like looking back. on yourself at times when you were settling, don't you feel like, oh, what was I doing? Yeah.

Starting point is 00:02:40 I almost like closed off this whole amazing life that I have for myself if I had kept going in that path. So how can you figure out if you're settling then? So the mini exercise is think about where you are today. And if you were to continue in this path for the next 12 months, would you be happy with where you end up? And if the answer is no or if you just feel yourself kind of like shrinking away from the answer and unhappy with it?

Starting point is 00:03:05 that means you're settling. Okay, so now that we've talked about how to know if you're settling, we're going to talk about why women and men settle. So high achieving people, especially women, are trained to endure. We're trained to not want too much, to be grateful, and to wait our turn. And we end up internalizing that. Oh, yeah. And there are so many studies that support this. So the one that comes to mind for me is most recently in 2020, Stanford did this study about women and basically how they put themselves up for promotion or how they don't put themselves up for promotions. So the takeaway is that women in leadership consistently underestimate their readiness for promotion, even though objectively for all the women in the study, they actually were outperforming

Starting point is 00:03:52 their male peers. So it's not just lack of opportunity for women. A lot of times it's more so this sense of lack of self-belief, which is also reinforced by our existing patriarchal systems. Yeah. And I think they're really hard part about that and especially about hearing that study is that settling isn't always like a dramatic thing that you see in the workplace or in your personal life. It can feel like a like steady drift into settling and not realizing that you're there until you're actually there. Right. I feel like that's actually why it's even more dangerous. Nefarious. Yeah. It's like insidious. You don't realize you're settling until you watch this episode. And we ask you, are you? Are you? settling. Yeah. And it's like also an uncomfortable thing, like an uncomfortable conversation to have with your friends too. Because I think from the outside, if you see one of your friends settling in the workplace or in their like personal lives in a relationship, it's also a really hard thing to call out. So I don't think it's like talked about enough. No way. No one would ever call someone out for settling. I mean, it's even like a harder, it's even a hard conversation to have with yourself. Yeah.

Starting point is 00:04:58 It actually reminds me of this concept called value drift. And it's this concept that, people slowly disconnect with what really matters to them and they don't even realize it, but they're feeling all these side effects, which are burnout, resentment, and loss of identity. So have you ever called me out on settling before? Not that I can remember, but it seems like you. Well, I mean, not like explicitly, but I feel like I've always like pushed you to do more than you thought you wanted to do at times, right? But that's not settling.

Starting point is 00:05:31 I feel like that's me not knowing my potential or understanding my potential and you widening my horizons. I don't settle. I'm just kidding. I have in relationships when I didn't realize that like I thought this was a good thing on paper, but then like, you know, in reality it wasn't exactly what I needed or wanted. Yeah. But did I ever call you out? I can think of one time. I sort of called you out for settling, is.

Starting point is 00:05:58 Okay. Okay. I'm nervous. Well, no, it was when maybe this is, again, back to the potential thing, but it was when after you had gotten into Stanford GSB and you had already left LinkedIn. Yeah. And you had the whole summer. And I was like, and you had that job offer to work at Bain Capital Ventures, which I was like, hello, this is incredible. And you're like, well, I don't know.

Starting point is 00:06:22 Like I was planning to just create content. Yes. I wanted to pursue my content career full time. I thought you were just going to hang. No. Well, I wanted to create content full time before school started to like experiment and see if that was a viable career path. Lo and behold, here we are. But I think my take at the time was I was like, well, this is an incredible way to create content. Like once you have this internship as a VC intern, like what an amazing way to, you know, show everyone in the world like what it's like to do this. Yeah. No, I think that's that's as close to calling me out as possible. Have you ever called me out? Yeah. I have. Do you know what I'm going to say? No. Maybe. I don't know. I've only called Jean out once in her life. Oh. Yeah. Honestly, for settling. And it was with her last relationship. If you see a friend or someone you care about who is settling, it is, and the reason why I said it's a hard conversation is because

Starting point is 00:07:24 it's really hard. Because one, you don't want them to feel any resentment for you for bringing something up that might be like a really hard truth to swallow. Especially when it's a type one irreversible decision. Yeah. We talked about on one of our other episodes. Yeah. So it was in her last relationship where I saw some things. I observed some things and I wanted to bring it up to Gene.

Starting point is 00:07:47 And I did. And only like maybe once or twice. It wasn't something I brought up on a weekly basis because I knew how the importance and the weight of my words and how to navigate the situation very carefully. So I did bring up and settling wasn't quite. how I phrased it, but that's how I felt in the bottom of my heart. Yeah. So I brought it up to you and-

Starting point is 00:08:07 How do you phrase it? I don't remember. Well, I was just like, I'm really concerned. This is coming from a place of concern. I see some things after like, you know, observing time spent with you and this other person. And here are some things that I just don't think are good objectively as your sister, as objective as I can be. And I think you deserve more and better.

Starting point is 00:08:28 And it was really, really tough for me to say. and I think even tougher for you to hear, especially because if your friend or your loved one is settling, it's, and you want to bring it up. You don't want to be wrong, you know, and like, yeah. Yeah. Like if you tell like a friend, you're like, I think you're settling with the person that you're about to marry and they end up marrying that person and like you have to go to the wedding and see them. That was a close one. That was a close one. That was a close one. We did get engaged. Yeah. But like that's also just not easy in it of itself. Like that's not a good conversation, like a fun conversation to have. But I also think it's also kind of saying like, not that I don't trust you, but you might have a blind

Starting point is 00:09:09 spot. That's what was really hard about it. I trust you to make the decision, but this is something you might not see that I am seeing from the outside. Yeah. That's why it was hard. I mean, it's also hard in general because it's probably something they don't want to confront about themselves. I mean, it must be. Yeah. Yeah. fun times really fun times so yeah this podcast is real personal well it was a happy ending yeah in the end yeah and i think another reason why like myself and a lot of people don't actually confront it is because it's been shown that high achievers are very good at rationalizing and so i wrote down some of the lines that people say so i'm lucky to have this

Starting point is 00:09:59 it's not that bad. Everyone would kill for this job or this relationship. Yeah. So like if you've ever heard yourself saying those words to yourself or like thinking them in your head, it might be another sign that you're settling and you're not admitting it to yourself yet. Yeah. And I think it's really hard. One thing that we talked about a few minutes ago was that like if everything looks good

Starting point is 00:10:22 from the outside, like if it looks right on paper. Yes. If everything, you know, is like beautiful and like shiny and interesting. Instagramable. It's even harder to let that go because there's that cognitive dissonance of like it looks good, but it doesn't feel good. Yes. And what do other people think and perceive? Okay. So I have another example that is not about my love life. It's about my work life. Can you make it about your love life? Just kidding. No. So my other example is just my last job where, you know, finally I had worked so hard. I had, you know, worked 15 years in my career to get to this dream job. So like if you had told me, you know, five years ago, 10 years ago that I was going to be the head of product for augmented reality shopping and monetization at Snapchat. I would have been like, holy shit, like what? That's insane. That's my dream job. But like by the time I was like actually in that

Starting point is 00:11:14 role and in earnest doing that role. I was I was really disengaged by the end. Like I was like 85% of the worldwide population is actively disengaged according to Harvard Business Review. But no, it's, It was crazy. Like I almost couldn't even reconcile it with myself because you worked so hard to get there. I worked so hard to get there. And then finally I was in this position where honestly I was doing less actual work than I had ever done in my entire life. Like a lot of my job was just to like tell people what to do and like, you know, try to make things happen, et cetera. Which is hard in and of itself.

Starting point is 00:11:50 But it was less like actual work than I had ever done. But I was so tired from it. Like I was so, so drained. And I couldn't figure. out why. Yeah. I mean, I think I knew deep down, but again, I wasn't admitting it to myself. Yeah, because of the shiny exterior. Because of the title, because of the pay, because I'd worked so hard to get there. That's some cost, fallacy. Yeah. Yeah. Kind of when you're there, when you've been working so hard to get there and your heads down, it's just like, now what? Well, and also, like,

Starting point is 00:12:18 in my instance, I felt like I had sort of, like, defied all the odds to get there, too. Like, I felt like it to, yeah, like, fight tooth and nail and, like, fight against, a lot of things. The patriarch being one of them. I wasn't going to say it again, but yeah. Yeah. And we have a mini exercise to help you figure out if you're settling and why. So the mini exercise for this section is to complete the sentence. I'm scared to walk away because. Because when you finish the sentence, your fear will show where you've tied your worth. And once you name and label it, it can make it much easier to figure out if you are actually settling. Okay, so next up is the science of why we stay too long right after this quick break. Applying to business schools,

Starting point is 00:13:03 it's a lot. We know. Every decision feels high stakes. Where to apply, when to apply, how do you stand out? You're Googling everything alone, hoping you're not making a huge mistake. Those months applying to business school, they were some of the most stressful of my life. Having an expert to guide you through the complicated application process, that's a game changer. And that's why we've partnered with MBA mission. They're offering Tiger Sisters listeners free, personalized one-on-one MBA consultations. You can ask their experts anything and get advice you can use right away. The essays, the interviews, sharpening your own personal narrative, think of them as your own personal counselors to help you with the entire process. They are the leaders in MBA admissions

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Starting point is 00:14:18 Now back to our show. And we're back. So let's talk about a term called cognitive dissonance, which was first coined in a 1957 Stanford study, and it's about the feeling that you have in your mind and your body when your actions don't align with your values. So when you value growth, but you stay in a job that you hate or a relationship that you know that's not right for you, your body and your brain signals distress. That's why you get irritable. That's why you have anxiety. It's literally your body telling you something is not right here. Right. And the question,

Starting point is 00:14:55 of why we stay too long, a lot of it can be answered by the things we've talked about already. So fear of regret, sunk cost fallacy, and external validation. Like, everyone thinks this job is so amazing. Like, everyone thinks my relationship is so great. Those are, like, the main reasons. So one way to think about it, if you're afraid of leaving, what if you were afraid of staying? It could be much more scary or dangerous in the long term. So next, we have another mini exercise, and I'm really excited about this.

Starting point is 00:15:25 one. Okay. So this one is to rate your alignment on a scale of one to 10 in three different areas, career, relationships, and your personal identity. And anything under a seven is actually a beige to red flag to sort of reevaluate that area. This is actually something that I do quite often. It's not like a monthly activity, but maybe like every, I try to do it every three months or every quarter just to feel like to ask myself like am I in sync with yeah what's going on in my life is everything like in homeostasis and oftentimes the answer is no like sometimes I'm feeling like you know in my relationship I'm not like 100 I'm not like 10 out of 10 if I am a 7 out of 10 like then I like I'm like wait why do I even feel that way like what is the reason and I can dig deeper

Starting point is 00:16:13 too excuse me good bless you and I can dig deeper if I have like the mental capacity to the time to and the willingness to. And that's okay if I don't, right, at that point, but it's just making sure I ask myself. Excuse me. She can dig deeper. Dig deeper. I didn't realize you did it so often. Yeah. You must be in the like top 1% of people who are probably. We're like reevaluating themselves. If you do it every quarter. Yeah. That's a lot. But I don't think you don't even need this many exercise. It sounds like a lot, but it doesn't have to be a lot. It doesn't have to be like you sit down for like an hour and a half and like journal for all that time and meditate. No, it's kind of just like asking yourself like, am I happy in my career right now? And like being okay that like the answer can be no. Yes. And it doesn't have to be like yes, I'm so happy all the time. Like life is great. Like it's okay that the answer is no. But then asking yourself afterwards like a follow up like why is it no? Like are there things that I can, because I want to be happy. Are there things that I can do to make it better for myself? Are there things that are within my control or is it out of my control? Or is it out of my control? or is this seasonal?

Starting point is 00:17:22 Like it's okay to ask those questions and like have an answer that you're not satisfied with. Right. Yeah. So just like the mini exercise I just described. That's what I'm saying. I like doing that. Yeah.

Starting point is 00:17:33 That's cool. Yeah. It's something you are already doing. Yeah. As a practice in your life. Yeah. Okay. So now we've talked about the symptoms of settling, why people settle and why we stay for

Starting point is 00:17:44 too long. Now let's talk about how to know if it's actually time to move on. And we'll get started right after this break. Quick pause, Tiger fam. This is Sheree, and we just dropped a brand new listener survey. It's different from the audience survey that you hopefully already filled out. It's 10 quick questions and 2 minutes max. Your support keeps the episodes free and publishing weekly. Why?

Starting point is 00:18:07 Because your answers tell future sponsors that Tiger Sisters is a show worth investing in. That means better partners, stronger episodes, and no random ads you don't care about. Tap the listener survey link in the description right after this episode. Knock it out and help us keep building a podcast that feels made for you. Thank you from the bottom of our hearts for being the best part of Tiger Sisters. Now back to the show. So you know it's time to move on when you ask yourself these three questions. The first is, does this version of me only exist to serve other people's comfort?

Starting point is 00:18:42 The second is, am I becoming someone that I admire? And the third is, would the woman I want to be say yes to this? These are pretty intense questions. They're big questions. Yeah. And what if the answer is no? Then you have your answer. And I think that's a very good thing to understand about yourself.

Starting point is 00:19:01 These are not questions, I think, to shy away from. It's scary, but it's only for the better that you know. And actually, we have this great case study about someone that I think she probably asked herself these questions. And it's about Reese Witherspoon, who founded Hollow Sunshine, which, is a company that we really look up to. And we think that, you know, Tiger Sisters can eventually be in that ilk. But the story behind Reese is that she obviously was this incredibly talented and super commercially successful actor. And she kind of sort of like threw that all away to start Hello

Starting point is 00:19:40 Sunshine because she wanted to create roles and wanted to work with people that were telling stories that she cared about. So like mostly women. Yeah. And I really love this story of Sunshine, one, because it's super successful now. So it's like fun to look at a success story, but also that it was born out of kind of like a problem that broke her heart in the way that, like, there weren't roles that she was getting that she wanted to play. And so if that's not in the environment that she's in, she created an environment and created a game that she wanted to play herself. Right. And I think that's so cool. Yeah. So she was like, I want to create this version of Hollywood that I want to be in.

Starting point is 00:20:20 Yeah. Like she was like, we're getting away from the place that I want to work. Yeah. She was anti-settling. Yeah. You know? Yeah. She like realized that it was not what she wanted and she did something really big

Starting point is 00:20:31 about it and created like a massively successful studio. Yeah. It actually reminds me of this other like concept I'll just talk about really quickly, which is that this idea of like zone of excellence versus zone of genius. So she obviously was in her zone of excellence because she was an award winning actor. But she wasn't in her zone. zone of genius because she wasn't doing something that she really like cared about and wanted to dedicate her life to. So she sort of like threw it all away and started anew doing something

Starting point is 00:20:58 she'd never done before, be a founder, be a producer, be a director. It's really incredible. And on this idea of zone of excellence, I think it sounds like a good thing, but it can be quietly like nefarious because if you are really good at something and it's, It looks shiny, kind of like we were saying before, shiny and good on the outside. You're like excelling in a field that other people are looking up to you for. But if you do not feel fulfilled or feel like you are in your zone of genius at the same time, it can be really easy to then settle. One quote I like is sometimes power means letting go of the thing you've built to build something even bigger.

Starting point is 00:21:40 And I think the reason I like it is because I feel like, it's about me. I feel like that's what I've done. Like I sort of threw away this 15 year long really successful corporate career to start over with just the two of us and build this thing that I've never done before. Like I'd never been on camera before this. Hopefully I'm doing okay job. Leave a comment below. Please give her success. Like give her comments.

Starting point is 00:22:04 I'm like always fishing for compliments. It's so embarrassing. Complementing comments on how she's, you know, doing well. They mean a lot and she reads all of them honestly. I really do. She needs the help with the very. validation. I need the validation. But yeah, that's what it really resonates with me, that one. So the last mini exercise for this video is to write a letter to yourself, but imagine that it's coming

Starting point is 00:22:28 from you five years in the future. What did she have to let go of to become who she is now? And I really like this exercise. This is just like write a mini letter. Doesn't have to be long. I've done a couple of like meditation and like manifestation exercises. Oh. Yes. where I literally like close my eyes and I imagine myself in the future. I imagine what I look like. I imagine the house that I'm in. I've done this too. It's an amazing exercise and it was a guided meditation and it like made me like burst out

Starting point is 00:22:59 into tears because your future self is asking your current, your, your current self is asking your future self a bunch of questions. And future me is so knowledgeable. She's so calm and confident. And it's really powerful to do this exercise because then you can kind of see what can be if you are not afraid of going out of your comfort zone and doing the hard reflections that we've kind of prompted you guys to do in this video. So I think if you can write a letter to yourself, imagine kind of your greatness.

Starting point is 00:23:34 Like step into that power. Imagine your greatness in five years because it's there. It's like you have all the answers within you inside you. do that exercise and I think you'll you'll learn some things about yourself that you might not realize like this very second. Should Sheree be a motivational speaker? That was really good. Is it? Yeah. I believe in, I think these exercises are so helpful for mindset. Yeah. Yeah. Yeah. And feeling grounded and realizing what you want. Yeah. Okay. And the very last part is just some really quick practical steps to stop settling. You don't need to blow up your entire life, but you do need to start listening to your intuition and your gut. And you could do this

Starting point is 00:24:16 with just starting with micro moves. It doesn't have to be a huge thing. So you can book an exploratory call or ask yourself these uncomfortable questions from the mini exercises or, you know, spend an hour acting like the version of yourself who knows exactly what she wants. I think if you're watching this episode and you decided to open this up, like I think your gut already knows that you are settling in some part of your life, let this episode give you permission to do something about it. Like, I think it's even worse to just sit back, feel that you're settling, know that you're settling, and literally not do anything about it. Like take one of these mini exercises. Maybe it's five minutes, maybe it's 10 minutes. Like think about it and then do something to then

Starting point is 00:24:58 kind of bring yourself, like give yourself a little momentum to like take the first step to get unstuck and then to stop settling. I'm going to give the listeners a little bit of grace actually and say that like a lot of times sometimes I think the hardest thing to do is actually admit to yourself that you're settling. I think for me that's a step that took years in some cases perhaps. And so I think if that's something that you haven't even done yet, that might be the most important thing that you can do that is sort of the output or the next step of this episode, right? Like actually admit it to yourself and like fully embody that. And then like both mark the episode. Come back to the episode in a few days or a week or once you've like really

Starting point is 00:25:43 settled with that sort of realization in your body. Come back to the episode and then do all the mini exercises. What is this? Good cop, bad cop? Why did I have to give the tough love? And then you have to give the nice advice. Next time I'll give a tough love. Okay. That's just our styles. You're mean and I'm nice. No. Hey. Hey. Yeah. And so I mean, be that as it may. Like yes, I was just the good cop, but I do still want to say and give some realism here that like think about yourself in a year, in five years, in 10 years. If you're looking back and you're like, hey, I'm still in the same place in this specific area that I feel like I've been settling, would you be happy with yourself? No. Right. So take whatever first step it is for you, whether it's actually acknowledging

Starting point is 00:26:28 to yourself that you're settling or doing all these mini exercises and taking the action to break out of your sort of settling mode and do it today. I think the scariest thing is a future of regret, regret for having not done something. So I think today is probably the day to like if you feel like you are stuck or you are settling, like do something today. Take that first step so that you don't feel that regret in the next year, in five years and in 10 years. And honestly, with hard things like getting unstuck, it's not going to be easy.

Starting point is 00:27:01 It's going to get like life gets hard. when you make a big change in your life. Life gets harder before it gets easier. If you need to go through a breakup, going through that process, going through a breakup, life sucks for a little bit, and then it gets easier. If you're changing jobs,

Starting point is 00:27:15 life sucks for a little bit, and then it gets easier. And so I realize it is going to be hard, but that's something you should confront now because in the next year, five year, 10 years, you won't regret it. Thank you for that, Sheree. And don't do this alone.

Starting point is 00:27:29 A lot of people, well, Gene and I have, like, personal board of advisors so that like when we're, you know, having these existential questions, which are pretty hard to answer. Like, you can call someone up, call a friend up, have this conversation with them. And also, as we said before, we read every single comment. And we love to see, you know, some of you guys move through these many exercises, any questions that you guys have and how you're thinking through these things. And we'll read through them and try to answer as many as possible. Yeah.

Starting point is 00:27:56 Treat the comments section like your board of advisors. True. Thank you guys so much for tuning in to this episode of the Tiger Sisters. If you found it helpful, please make sure to like, comment, and subscribe. And when you subscribe, you get notified when a new episode is released. Yes. And if you have some friends who you think they might be settling or playing small or not selling at all, but you just want to share Tiger Sisters with them, then please share this episode

Starting point is 00:28:22 with them. And we'd so appreciate it if you can give us a five-star review on Spotify or Apple Podcasts. It takes literally three seconds and it helps Tiger Sisters get discussed. Yes. And if you have 10 seconds, actually write a review because I've heard that those also make a huge difference in people deciding to listen to the episodes. Thanks, guys. We'll see you next time. Thanks. Bye.

Tiger Sisters - Are You Settling in Love or Career — and Don’t Even Know It?

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