How to figure out what you want with Simone Stolzoff

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2:46Simone Stolzoff: We can fall into the trap of thinking the next job you take will be the job that you have for the rest of your life. Or the stakes of this career decision are so high because we work more than we do anything else. But in actuality, if you understand that what you will want five years, ten years down the road might be very different from what you want today, it can help take some of that pressure off, help you understand that your job is a decision like who do you want to date as opposed to a decision of who do you want to marry.

3:20Hi everyone. Today we are kicking off a new work-life series called How to Get What You Want at Work. I'm pretty excited about it. One of the things I've noticed in all my conversations about people's careers and work decisions is that a lot of us are incredibly active in our careers without being particularly deliberate about them. We get on the career treadmill early, we get a good job, we get promoted, we make more money, we get a better title, manage more people, the bigger opportunity shows up. There's always another rung to reach for. So we just keep climbing. Often, somewhere in there, frustration creeps in.

4:04You're bored or exhausted. You want more responsibility or less responsibility, more money or more flexibility, or you hate managing people, or you want a bigger team. Despite that frustration and whatever is behind it, a lot of us just keep going. We complain about it and we push through it. Maybe we start looking for another job, but we don't necessarily stop and ask, what would actually make this better? What do I want to be different? And what would happen if I asked for it? What do I really want out of work right now? And what am I willing to trade for it? This series is going to get into all of that.

4:48And we're going to start at the surprisingly hard beginning. how to actually know what you want. There are two questions I talk about a lot when it comes to work. What's in this for me and is this worth my energy? I'm going to repeat those. What's in this for me and is this worth my energy? You can't really answer either of those questions unless you know what you're trying to get out of work in the first place. Why are you in this job? What is it that you actually want. I have found that to be really hard on a whole bunch of different levels. There are times when work is just draining. I can think of many versions.

5:32I've felt undervalued. I've felt frustrated with leadership. I felt stuck in a job that wasn't a fit. All the versions. I remember there was this one particular moment early in my career. I was about two years into a job, and I was just frustrated all the time. I definitely felt undervalued, but I was frustrated with the way they were running the company. I was frustrated with my boss. I was frustrated with all the decisions that were being made. And I went on a vacation. And I don't really know what caused me to do this, but somehow I was able to take a step back and to realize that being in this job was a choice.

6:08I realized I could probably go get another job if I wanted one. So there was a reason why I was staying. There was a reason why I was choosing to be there. I asked myself, Do you want to leave? And the answer was no. There was something I wanted out of that place. Having that realization, taking that step back, feeling that agency actually made all the stuff that was pissing me off less frustrating. I didn't feel as emotional about it because I knew why I was there and that I was choosing it. Work can be hard. Sometimes it's really hard. That doesn't necessarily mean that something is wrong. The question is, what are you getting in return?

6:52What makes all that time and energy and all that hard actually worth it? I'm Molly Graham, and this is Work Life, where we untangle the messy human side of work. My guest today is Simone Stolzoff. He was a journalist and worked at the design firm IDEO. Then he left and created his own job as a writer, speaker, and consultant. He's written two books, The Good Enough Job, about our relationship with work identity and meaning, and his new book, How to Not Know, about getting more comfortable with uncertainty, particularly in your career. He's been one of the favorite repeat guests inside my leadership community glue club, so I wanted to bring him on here.

7:37Simone has a lot of useful frameworks for figuring out what you're optimizing for at work and understanding the trade-offs that come with that choice. Because you probably can't maximize for money and flexibility and status and meaning and learning and time with your family all at once. Deciding what you want means deciding what matters most and what you're willing to trade away. Well, Simone, welcome to WorkLife.

8:06Simone Stolzoff: Thank you so much for having me. I'm a longtime listener, first time caller. We're happy you're here, finally. Okay, Simone, so you are an expert in getting people to rethink their relationships to work and to really push them to think what they want out of work. Why do you think that's so important? There's two reasons. The first is that we work more than we do just about anything else and how we spend that time matters. And the second is I am someone who doesn't know what they want from work. And so the cliche among authors is that you write the book that you need to read. In many ways, I've been my whole life trying to figure out what should I do?

8:51Simone Stolzoff: What do I want to spend my time doing in the professional realm? And so I've sort of written two books to try and answer this question for myself. So just talk a little bit more about your journey with this question of how to know what you want at work. Well, maybe the first red flag is that in college, I studied poetry and economics. And so you can probably see the existential crisis looming on the horizon. I went to Penn, which is a very pre-professional school. And while my friends were getting internships at consulting companies and investment banks, I was pretty clueless. And so I worked in advertising for a few years.

9:29Simone Stolzoff: And then I took an early retirement and left and traveled the world for a year and then came back and worked in tech for a few years. Then I went back to school and studied journalism. And then I worked in journalism for a few years. And so you can see this thread of me trying to find a vocational soulmate, a job that will help me self-actualize. And it all came to a head when I was about 28 or 29 or so. I was writing for The Atlantic and I had a job offer to join this prestigious design and innovation firm called IDEO. And on one hand, it's like, oh, the agony of deciding between two attractive job offers, you know, world's smallest violin.

10:07Simone Stolzoff: And on the other hand, it really sent me for an existential loop. I'm sure you and many of our listeners have been at similar career crossroads where they sort of see these two paths unfolding of who they could become. And it really didn't feel like I was choosing between two jobs as much as it felt like I was choosing between two versions of me. There was two insights that came out of that moment of tumult for me. The first was this recognition that my job, my identity had become so entwined. And the second was that I was looking for certainty where there was no certainty to be found. I thought that if I just banged my head against the wall at the right angle, I would know which of the two jobs I should take.

10:46Simone Stolzoff: And in actuality, sometimes in life, as I'm sure we'll get into more later, you have to make choices without knowing exactly how they'll turn out. And so that first insight about work and identity became the topic of my first book, The Good Enough Job. And that second insight about needing to be able to tolerate uncertainty became the topic of my second book, How to Not Know. I love it. And I think I like that what you do is take your own quest and turn it into a way to help other people with their quest. I want to just before we get into a lot of what you just talked about, I do want to like take a step back and just name that like when people when we're talking about like how to know what you want at work, a lot of people are like, what do you mean?

11:29Like I work for money. Like that's why I work. Like I work for a paycheck. I work for security. I work to take care of myself and my family. Um, so in your opinion and your experience, like how should money fit in to the question of figuring out what you want from work?

11:46Simone Stolzoff: It's vitally important. And I like to think of work as sort of a bundle of different jobs to be done, so to speak. At the most base level, you need a job that allows you to pay for your material existence. Sometimes we call work our vocation or our passion or our callings. But at the end of the day, work is an economic contract. It's an exchange of your time and your labor for a paycheck. And if you accept a job that doesn't allow you to pay rent or doesn't allow you to continue to support yourself for those that you love, maybe it's not a good enough job for you, even if it is the perfect alignment with your passions.

12:27Simone Stolzoff: And the good enough job, the central argument is that rather than looking to work as a dream or as your primary source of self-actualization? How can you find a job that allows you to be the person that you want to be in the world? And part of the interesting nuance of this question of how do you figure out what you want to do is that different people have different needs when it comes to work. For some people, work is their primary means of finding purpose in the world. For other people, their work is a means to an end so they can find their purpose when they're not working. And so when we ask the question, how do you figure out what you want from work?

13:09Simone Stolzoff: We're talking to people on the whole spectrum of people that live to work and people that work to live. And so there's no prescriptive one size fits all answers here. I think that makes a lot of sense. And I think, you know, one of the things I talk about with risk taking is there are certain things you can't do if you're terrified about money and security and food and your family. And that's part of what I hear you saying and sort of like the part of what money enables you to do is ask some higher level questions about work. Talk about the other side for a second, though. Is there a trap in only optimizing for money?

13:53And how do you think about sort of the trade-offs between things like money and time and flexibility and all that?

14:01Simone Stolzoff: Yeah. So money is a great example of what a organizational psychologist might call a source of extrinsic motivation. It's like a carrot that you can chase. And the problem is if you are only working for extrinsic motivation, like money or like a fancy job title, you can spend your whole life reaching for these carrots without ever feeling full. There is this great book called Drive by Daniel Pink, where he really takes down this idea of the carrot and stick approach to motivation. And what he says is instead we really have to think about intrinsic motivation, which he names three component parts for.

14:42Simone Stolzoff: The first is autonomy, the feeling like you are the protagonist of your own story. The second is mastery, the feeling that you are building skills and developing a level of expertise. And the third is purpose, the idea of working towards something that is larger than yourself. And I think those three questions can be great questions when it comes to our careers. You can ask yourself, what is it that I hope to learn from this next season of my work life? What is it that I hope to contribute to larger than myself? And third, how can I find a sense of autonomy or agency over my own direction of my career?

15:23Simone Stolzoff: So rather than just think about the quote unquote resume virtues, the things that look good to the outside world, focusing on those intrinsic motivators tend to be a much more sustainable fuel source over the long term. Sometimes it's just easier to focus on those extrinsic things. And if the goal isn't simply just make as much money as possible or get the fanciest title in the world, you actually do have to figure out what else you care about. And as you said, in your story, that can be really hard. I find it easier sometimes to know what I don't want than what I do want. You know what I mean?

16:01Like, why is it so hard, Simone?

16:06Simone Stolzoff: Because we all have scripts in our heads that are telling us what it is that we should want or what we could want. And it's hard to get quiet enough to figure out what exactly it is that we do want. Another factor is that what we do want changes. So I am a father. I recently had my first kid, or I guess my wife recently had her first kid. And it completely changed my relationship to work rather than just optimizing for my own hedonism, my own pleasure, the own alignment between how I'm spending my time and exactly how I want to be spending my time. There are now other factors that are in the equation of me looking for work that is fulfilling, yes, but also is sustainable for the life that I hope to contribute to my family.

16:56Simone Stolzoff: And so these changes around life circumstance, age, they can really change what we want in our life. If you think about who you were 10 years ago, you probably wanted things that are fairly different from what you want today. Psychologists sometimes call this the end of history illusion. When we think back to a former version of ourselves, it's very easy to see all the ways that we've changed or evolved or have new desires. But when we forecast into the future, we often assume that who we are today is fixed, that our current needs and desires and preferences will remain our needs and desires and preferences for the entirety of our lives.

17:40Simone Stolzoff: this realization that we will continue to evolve is actually quite freeing in my mind because we can fall into the trap of thinking the next job you take will be the job that you have for the rest of your life or the stakes of this career decision are so high because we work more than we do anything else but in actuality if you understand that what you will want five years 10 years down the road might be very different from what you want today. It can help take some of that pressure off, help you understand that your job is a decision like who do you want to date as opposed to a decision of who do you want to marry.

18:19Yeah. I mean, part of what I hear you saying is like these decisions almost aren't as important as you think they are. They aren't as like deterministic as you think they are. Is there something about like scarcity versus abundance or something that can help people kind of hold these things a little more lightly?

18:33Simone Stolzoff: One question I like to ask myself is, is this decision a one-way door decision or a two-way door decision? It's a framework that was popularized by Jeff Bezos, but has been used many times in especially the business world. And the idea here is, is this decision easy to reverse? So yes, there are some decisions in our life, like should I buy this house, should I marry this person, that require a lot of deliberation and maybe a very analytical thought process. But the majority of decisions we make in our lives are actually these two-way door decisions, where if you walk through the door and you realize that you've really messed up, there is probably a path to walk back through that door again.

19:16Simone Stolzoff: And I think choosing jobs is more of a two-way door decision than we give it credit for. You often can course correct or find ways to get back to a place that you were before if you decide that you made a very bad decision. Or we also have the agency to be able to what researchers call craft our jobs. So this idea that we can craft the job that we have to be more like the job that we want, or even mentally frame the job that we have in a different way that changes our relationship to it. Yeah, that's awesome. I want to come back to this idea of crafting an existing job around more of sort of like what you want.

20:01But I want to go back for one second to this sort of like, why is it so hard to know what you want? And, you know, one of the things that certainly haunted me in my life is sort of like the shoulds, you know, like you should want these things and that like there's things you're supposed to want, like programming. certainly, you know, from my upbringing and things like this. You have a concept, I think, called ladder logic that I would love for people to hear about. But I also just want to hear a little bit more from you on like, how do you tell the difference between something you genuinely want and something that you were sort of like programmed to want?

20:45Yeah.

20:46Simone Stolzoff: So ladder logic is essentially the idea that progress means moving up, moving up in a career ladder, moving up in a pay grade, always seeing this sort of linear path from maybe intern up to the C-suite. And success means up and to the right. One of the benefits of ladder logic is that it's very legible. So as I mentioned, I have lots of friends that out of college went into fields like consulting or finance. And one of the benefits of those fields is they make career progression really easy to see. In a field like consulting, maybe you start as an associate, and then you become a senior associate, and then you become a director, and then you become a VP, and then you become a chief something or other or a partner.

21:38Simone Stolzoff: And when there is this carrot that is constantly dangled ahead of you, it's really easy to just say, okay, this is what I value. I value what the firm values. The problem is by solely chasing those carrots, that next promotion, that next raise, it can quiet that voice inside of you that tells you what it is that you actually want. Sometimes this idea is called value capture, where you sort of buy a value system off the rack and you say, because the firm has this in the performance review, or this is the rubric that will get me to that next pay grade, that is also what I value. But finding alignment requires you to be able to take a step back from what the institutions or your managers are telling you should matter and being willing to check in with yourself.

22:31Simone Stolzoff: The problem with taking that approach is that no one else is going to make that decision for you. And that is both the blessing and the curse of not being part of these larger institutions. Yeah, totally. It's funny you said that you can buy, you know, sort of like pick off the shelf the corporate values. And I have this saying, this phrase, like you can end up optimizing an anthill when you're inside of a company. Because I see a lot of people end up sort of feeling like a performance reviews define their entire self-worth and value. And, you know, I had a conversation with a friend who's at a pretty big company the other week and they were like, I think I need to go out, you know, for this manager role because it just opened up.

23:15And I was like, well, do you want to manage people? And they were like, no. And I was like, do you want that? Do you want to do that job? And they were like, no, but I just think I like, I'm supposed, like I should, that's the way to get more senior, you know, like that's the job that's above me. And I was like, wait, you're like in the classic case of an anthill where you're going to optimize the shit out of this thing and you're going to get to the top of this hill and then just be like, where am I? Why did I do that? So part of what I hear you saying is trying to understand the why behind what you're optimizing for.

23:49Simone Stolzoff: So many people that I talked to for the Good Enough Job in particular were those anthill optimizers. They were the type A, highly ambitious people that, in the words of one Yale professor, would climb the greasy pole that was put in front of them. They were world-class hoop jumpers. And yet once they got to the top of the ladder, they had the common feeling of, is this it? Is this all that I've been working for for my entire career? And so as I mentioned before, Or there's real risk in just paying attention to what the market values without considering what it is that you yourself value. But on the other end of the spectrum, there's a risk of just paying attention to what you value without considering what the market values.

24:35Simone Stolzoff: I think that's the balancing act of trying to figure out what you want. How can you think about not just what you find desirable, but also what the market will pay for?

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27:57let's talk to someone that's sitting in a job right now and feeling unfulfilled um and they're not sure why what should they do like how can you start to figure out what it is that you actually

28:12Simone Stolzoff: want the first thing that i always tell people i teach a class on this called designing your next career step where i try and help people figure out what they want to do next for their career is to clarify your values. So there's a few ways that I like helping people get clear on their values. One is a narrative approach where you can think back to moments in your career where you really got to show up in the way that you wanted to show up. They don't have to necessarily be the sparkliest moments, the day you got the promotion or the day you got the raise, but a moment in time where it felt this is exactly where I want to be.

28:49Simone Stolzoff: And then almost like an anthropologist trying to dissect that moment for its component parts. What about that room or that conversation or that collaboration or that phase of work was fulfilling to you? And maybe by dissecting that moment in time, you can understand some of those underlying values that are things that you really need from your work life. Another approach is to just take it more practically and do something like a card sort. So there's this group of psychologists who came up with this philosophy of psychology called ACT, Acceptance and Commitment Therapy. And they created this card sort of sort of like a game where you can stack rank all of these different values and come up with your list of five or 10 of your favorite values.

29:39Simone Stolzoff: What I like about that is it sort of takes you out of the moment of your particular job or your particular career and helps you think about your life more broadly. And I think this can be a very big unlock for some people, which is to say that, yes, I have all of these values. How many of them do I need to express through my job, through my work life? And how might I express some of them in my life outside of work as well? Interesting. Wait, so just go back to the values thing again. Explain what, like without using the word value, like what are people looking for? They're looking for a set of words that serve as like a compass in decision making basically?

30:19Simone Stolzoff: Exactly. I think a compass is a great metaphor. Rather than needing a map of exactly how to progress in your career or reverse engineering someone's career path from LinkedIn, you want these things that are your guiding lights where you can pick up this compass wherever you find yourself. For me, for example, some of my values include creativity, collaboration, and novelty. And so through my work, I want to find ways in which I can collaborate with people that I really respect. I want to find ways that I can create. And I want to find ways where I can be exposed to new scenarios. Got it. And to some extent, are they also a tool to look at what might be missing?

31:05Like if you're sitting in a job sort of feeling like that you can look at the values, like if you do that exercise and be like, oh, I'm not feeling like my creativity is harnessed kind of thing.

31:15Simone Stolzoff: Exactly. You can ask yourself, am I learning the things that I want to be learning? Do I feel connected to the purpose of this job? And does it feel like I have another sense of autonomy? Another framework that we often used at IDEO in product development was this idea that the best products sit at the intersection of desirability, feasibility, and viability. So desirability is, do I want this? Feasibility is, can I make this? And viability is, is this sustainable? In the frame of careers, it's, is this a job that I want to be doing? Is this a job that I have the skills to do? And is this a job that can support me sustainably over a longer time horizon?

32:02I like that a lot. Just to stay on the sort of malaise question for one second, like, how do you distinguish between there's something fundamentally wrong with this job and I need to get out of it and either I'm having a bad six months or there's some part of me that's unfulfilled that I can fill outside this job.

32:27Simone Stolzoff: Yeah, it's a hard distinction to make and especially hard to give advice from a literal armchair. But one question that I'd be asking is, are there things outside of your work life that are confounding variables right now? So are you having sort of a crisis on the home front? Are there things outside of work that are influencing your relationship to the job right now. The second thing I'd say is, do you have the ability to make the job that you have more like the job that you want? Can you craft the job either in the way that you frame it or literally have a conversation with your manager about doing more aspects of work that brings you joy or brings you fulfillment?

33:11Simone Stolzoff: And if the answer is no to those, then maybe it is time to make a change. But often I think that people assume making a change means making a big leap, sort of quitting the job and then figuring out what they want to do after that. And what I often tell my students is it makes more sense to think about the experiments that you can be running to help you get clear on what you actually want. So rather than have this sort of binary thinking where it's like I quit this job and then I find my passion and then I'll never work a day in my life, I often advise people to canvas out at least three different paths.

33:56Simone Stolzoff: Sometimes they call this odyssey planning. It's a tool that comes from the Stanford D School. And one path is a continuation of what you're doing. So what would my life look like in one, three, five years if I just keep doing exactly what I'm doing today? Another path could be if your current path is no longer an option, what would you do? So what is sort of the adjacent possible of what it is that you're currently working on? And then the third is maybe what if money was no object? What if there was no social ramifications of your choices and you could just follow your heart without having to think about some of those material needs.

34:38Simone Stolzoff: And so rather than thinking about these decisions, like there's one perfect path or there's one right choice, and you just need to bang your head against the wall until you figure it out, laying out these different potential paths for yourself allows you to see that on any particular path you choose, there'll be trade-offs. And you have to ask yourself, what trade-offs am I most willing to accept at this phase of my life. Yeah, totally. I love Odyssey planning, just to strongly endorse it. It's something we, I've done, well, I've done it a lot because we do it in both my communities, but it is really shockingly valuable to force yourself to imagine different versions of your life.

35:18It's also outlined in the book, Designing Your Life, and it's like a really helpful, that can be a really helpful resource if you want to do it or try it. So, but I also loved what you said about experiments, because that's, that really resonates with me, which I think we sort of think of these things as big and dramatic, but sometimes you can run experiments sitting where you sit. And I assume this relates a little bit to your point about crafting the job you're in. So if someone is sitting, feeling unfulfilled, but just doesn't feel capable or able to make a big change right now, how do you think about crafting more of what you want from an existing job?

35:56Simone Stolzoff: I would think about it sort of similar to the scientific process. where maybe you have a hypothesis about what you might like doing more than what you're doing today. Is there a way that you can get proximate to the actual experience of doing that work? So for example, I'm an author. I get a lot of emails and DMs from people saying, hey, I'd love to write. I want to write a book. I have this aspiration to become a full-time author. And the first question I often ask is, so what do you like writing? What have you written recently? and I almost always get the same response, which is, I have all of these ideas about what I could write, but I haven't actually put pen to paper.

36:37Simone Stolzoff: And what I want to yell is the best way to figure out whether you like writing or might want to do this as a career is to write. It's not a thought experiment that you have to work out in your mind. And I think one of the great blessings of this age that we're in is a lot of the gatekeeping and permission-based structures have broken down, where you don't need permission to write an essay on LinkedIn or to start a sub stack or to send a newsletter or an email to some of your friends. You don't need a coding background to try out what that app that you've always been dreaming about might look like in reality.

37:18Simone Stolzoff: So what I'd tell our listener is don't just think about the romanticized best case scenario of any particular job path. Also think about what suck you're willing to put up with. There was this great op-ed in the New York Times a few years back called Why You'll Marry the Wrong Person. And it's by Alain de Botton. And he makes the case that often when we think about a romantic partner, we just romanticize their best qualities. And we think about all the ways in which they're lovely. But a better question might be in what ways are they crazy or what ways in which are they undesirable? And rather than just opting for your optimization of what you think is the best, it also makes sense to ask yourself what level of undesirability or suck am I willing to put up with?

38:07Simone Stolzoff: Because in any given job, there is bound to be some level of TDM monotony or things that you don't want to do. Yeah, totally. So is that part of thinking about what a good enough job is? By the way, I really agree with this. A lot of times I think we're just imagining the best case version of a job. And I always tell people, if the company isn't as successful as you think it's going to be, are you still going to be glad you took it? For me, that's a question that strips away a lot of the ideal of like, oh, it's going to, everyone's going to think I'm so cool and it's going to, I'm going to make a billion dollars and like whatever, where instead it's asking you to say, why am I doing this regardless of the externality, sort of what is truly in it for me?

38:58So is that how you get to the good enough job?

39:02Simone Stolzoff: The suck you're willing to bear. The suck you're willing to bear. I like the suck. That's good. Well, you know, the way that I think about a good enough job is it's a job that allows you to be the type of person that you want to be in the world. For one person, maybe good enough does mean having that fancy job title or working at this particular company or working in this particular industry. For someone else, a good enough job is a job that gets off at a certain hour that allows them to pick up their kids from school each day or go on that bike ride that is actually the central passion of their life right now.

39:34Simone Stolzoff: We get to determine what good enough means to us. And to your point about the sort of stripping away the things that are shining on the outside, I spoke to this ethicist for How to Not Know. And he's this really interesting guy. His name's Ira Bredzow. He works at Emory University. He's both an ethicist and a counselor for college students, helping them figure out their big questions in their life. And he says when people come to him with questions, he always asks the same three questions. The first is, what do you want? And the idea here is to get out of sort of an intellectualized sense of what you want and get into a more embodied sense of what you feel in your body.

40:18Simone Stolzoff: Two is, do you want to want that? Which is a little heady, but it's what philosophers sometimes call your second order desires. It's sort of your perspective on your desires. Do I want a cigarette? Sure. Do I want to want a cigarette? Maybe not. And the third question is the most important. What does that choice say about who you are? And the reason why I love that third question is it connects our decisions to our values and to our identity. Just like you said, Molly, we, at the moment of making a decision, can't know how the decision is going to turn out. And so we want to be able to make decisions that we can stand by even if we don't get our desired outcome.

41:04Simone Stolzoff: That's what I think it means to live in alignment or live in integrity with our career path is making choices where we can make plain the reasons why we're making those choices so that we can stand by them even if the company does an IPO or even if you don't get the accolades that you thought you might get coming in. yeah okay I'm having a lot of reactions as you're asking these questions because I'm like damn these are like esoteric or like I don't even know they're just very big questions so let's imagine I'm sitting with a job decision and I'm thinking back to like one of the ones I've made where I was like ended up kind of being a mistake in one in one version or another so the first question is what do you want and is the point there to get like underneath like I just want the job it's like, what do you really want out of this job?

41:56Simone Stolzoff: Let's get into your gut. Let's take away the spreadsheet that has the pro-con list. If I just had a gun to your head, you have to decide right now, what do you want? Like, what is your first reaction to that question? Okay. So first question is basically like, why are you drawn to this thing? Or really what's the sort of like intrinsic, I guess, like motivator underneath it? And then are you like judging yourself essentially for it in the second question? Yeah, I think the second question gets into a lot of the scripts that we told ourselves, the shoulds. I want to take this lower playing job at a nonprofit, but I don't want to want to take that because I'm really stressed out about how I'm going to be able to afford to buy a house in the Bay Area, et cetera.

42:39Simone Stolzoff: It taps into that second order of thinking, that sort of perspective taking on your most base desires. Yeah. Or like the other version, which is like, I want to take this job because it sounds so cool. And my friends are going to think I'm cool. And if it's successful, I'll look awesome. But do I want to want that? It's like, no, I want to not want this because that job is going to be miserable and hard and like, whatever. OK, wait, what's the third question? What does that choice say about who you are? Dude, there's a lot of judgment in these questions. Yeah. I mean, I think that sort of strips away a lot of the BS that we dress up these decisions around.

43:28Simone Stolzoff: Another way to think about this third question is an idea that I learned from this woman named Ruth Chang. She's a philosopher at Oxford. And one thing that she says is, the reason hard decisions are hard is because one option is not clearly better than the other option. If that were the case, it would be an easy decision, right? We don't agonize over easy decisions because the path is very clear. What makes a hard decision hard is that one option is better for some reasons. The other option is better for other reasons, and neither option is better overall. And so Chang's advice is spend your energy not in deciding between these two things that will have huge trade-offs either way, but in getting very clear on the reasons why you make any choice that you do make.

44:17Simone Stolzoff: Through action, that is where clarity comes from. It's not from listening to a million podcasts on how to make a decision or interviewing everyone that you've ever met in your life or creating this perfect spreadsheet of pros and cons of every decision. It's by making choices and then trusting in your future selves ability to adapt that we are able to learn about who we are and what we want moving forward.

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47:09I remember like one moment when I was deeply stuck at work and feeling pretty much in like a dark, dark hole. I really felt paralyzed by it and I didn't know how to move forward. And I had a conversation with a coach and I said, you know, I just know that when I leave this job, I'm going to get completely lost. And she looked at me and she was like, well, nobody would ever want to do that. So like, let's have a conversation about reframing, like what you're telling yourself about what's going to happen after this. But, but I'm curious, like, I mean, I think part of what I was struggling with at the time was like the not knowing.

47:46Do you know what I mean? That, that, that I had no idea what I wanted to do on the other side of this thing. So how much do you actually need to know in order to move forward? Cause I, I totally agree with your point about like action creates more knowing and you just got to sort of figure out the first step. But sometimes it can feel hard to even know what that first step is, you know?

48:06Simone Stolzoff: I think it depends on the person. And one of the things that's important to understand is that you have to know thyself. You have to know what Molly tends to need to make a particular decision. I have friends that are super intuitive and they never think twice. You know, like my sister, for example, she had never taken a science class before in her life. She decided one day when she was 24 that she wanted to be a doctor and now is in medical school and has never looked back. Me, I know that I am a naturally doubting person. Every single choice in my life, whether it's what to have for dinner, who to marry, what job to take, sends me into some form of analysis paralysis.

48:49Simone Stolzoff: And so what I need is to be able to get to the point where I'm taking a step, even if that step is in the wrong direction because it's through that action that I actually figured out what it is that I want. And so when people are really stuck, sometimes what I advise them to do is to go out into the world and do something that is not related at all to this career decision that you're trying to make or this romantic decision that you're trying to make and find some novelty. I hear like people being scared of failure, right, or making the wrong choice. And I certainly get questions like that all the time of like, even just personally, like, have you ever made a decision or taken a risk that you regret, like that you wish you hadn't taken?

49:38what happens, you know, because, you know, I talk about risk as cliff jumping and they're like, what happens if you never hit the bottom and you just keep falling, you know? And my answer to that is always like, to be honest, even the risks that I've taken that I like wouldn't take again, knowing what I know now, I'm glad I took them because the failure or the learning was the point, right? That it moved me forward, which I think is what you're saying too, which is like any step is better than no step? Yeah.

50:07Simone Stolzoff: This is another robust psychology finding, which is that when you think about regret, people regret the things that they didn't do much more than the things that they did do that didn't work out. And so this is another sort of framework that you can use is around regret minimization. What choice would you regret not having done more. Yeah. I love that. Okay. So you've talked about the fact that this changes over time and that's certainly something I've really experienced that what you want in your 20s is different than what you want in your 30s and 40s and 50s and 60s. How do you know when it's time to revisit those values or when it's time to re-ask the sort of what is good enough right now question?

50:57Simone Stolzoff: One thing that I like to think about is when gathering information has diminishing returns. So I'm one of those people that when I'm trying to make up my mind, I like to externalize my thoughts. And I like to ask my friends or my wife or my mentors about them. To a certain extent, it's a way of abdicating myself from the responsibility of having to make the choice. I can say, Molly told me to take job A. You're outsourcing it. Yeah, exactly. Or I could say, if I just sort of like triangulate the truth by talking to all of these different experts, then I'll know exactly what I want. And in those moments, I often see it as an avoidant tactic to get away from having to do the introspection to figure out what it is that I actually want or what it is that I actually value.

51:51Simone Stolzoff: In How to Not Know, I write this chapter about a guy named Max, who is a computer scientist and an artist, and he designs an algorithm to make all of his life decisions on his behalf. It starts by he creates an app that brings an Uber to his house that will bring him to a location in the city known only to the driver. So he can sort of explore a different part of the city. And then he starts doing the same with public Facebook events where he can press a button and it'll tell him an event to go to and he'll go. And then he starts doing it with where to live. And he creates an algorithm that tells him where in the world he should pick up and move.

52:28Simone Stolzoff: And for two years, he just traveled around the world, listening to the computer at every step in the way. And at first I thought he was this sort of master of uncertainty, this guru who was able to show up to different circumstances and be okay with it. And I talked to this psychologist named Mikel Dugas about Max's story. And he said, you know, when I come across people who are really intolerant of uncertainty, I see one of two main behaviors. The first is people become super information gatherers where they need to say, read 300 reviews before they buy a plastic water bottle on Amazon. But the other category of avoidant behaviors that I see is that people become really impulsive.

53:15Simone Stolzoff: They just sort of buy the first thing that they see because they don't want to have to deal with the uncertainty of having to weigh their options. And what we need to be able to do is find a middle ground. To make a decision about the future is to cast a line into an unknown. It requires you to be able to sit with uncertainty and not know how it'll turn out. And even though you might play mental tricks on yourself and thinking that you worked out what is the perfect job or you know exactly what the future will hold, we as a species are very bad at making such predictions. And so what we have to be able to do is make a choice to the best of our ability and then be willing to tolerate the fact that we don't know exactly how it'll work out and trust that a future version of us will be able to adapt from there.

54:17Yeah.

54:17Simone Stolzoff: There's one more tool that I'll offer to our listeners that might be helpful. It's a tool that comes from this woman named Annie Duke, who used to be a professional poker player. Now she is a professor and a decision strategy coach. And she taught me about this idea called the only option test. And it goes like this. Imagine you are deciding between going on vacation to Rome or to Paris. The decision feels pretty high stakes because you might not get very many vacations like this in your lifetime. It's expensive. You have to spend a lot of money. There's an opportunity cost to whatever it is that you decide.

54:50Simone Stolzoff: And he says, imagine for a second that someone came to your house and said, your only option is to go to Rome. Would you be happy? Okay. Now imagine the next day, someone else came to your house and said, your only option is to go to Paris. Would you be happy? And if the answer to that question is yes, both times, the decision probably matters a little bit less than you think. Which isn't to say that the decision itself doesn't matter, but if you feel like you could be happy with either option, maybe the real advice is that you just have to make a choice. Yeah.

55:32You know, it's interesting. I had this conversation with someone who was talking about the Robert Frost poem, you know, the road less traveled. And she was like, it's interesting because people think that that poem is, you think it's about sliding doors, right? That you pick one road and it changes your life forever. And she was like, if you actually read the poem and you interpret it, what it's saying is that it doesn't matter, that both roads are good. And actually that both roads might lead you roughly to the same place. I think part of what you are saying is actually, it's like, if you imagined that you would end up in the same place, regardless of which decision you make, which would you make?

56:09Because which life do you want right now? What do you want the dynamics of your life to be like, kind of like regardless of the outcome? And I think that is like one of the things I'm hearing, which is you have to envision the life you want, which you have the beautiful saying, like, who do you want to be in the world? Is that what the good enough job is?

56:30Simone Stolzoff: Yeah. What job allows you to be the type of person that you want to be in the world? Yeah. And that's such a much bigger question than what job you want. Work is a part of that, but not all of that. And if you have the answer to that, then you have your why of like, why this job? Is there anything else you would want folks to know that are listening as they're thinking about how to figure out what it is that they want? There's all these other heuristics that you can use. But at the end of the day, one of the skills that we haven't talked about is the value of optimism. And part of what makes uncertainty hard is that our brains have a natural tendency to catastrophize.

57:15Simone Stolzoff: It's easy for us to think about all of the things that can go wrong. And this is self-protective. It's a way for our brains to keep us alive. When the future is predictable and certain, we feel safe and secure. But uncertainty need not be a threat. It can also be the birthplace of possibility. And so as you're making these choices for yourself, in addition to turning over every rock and asking what could go wrong. I just hope listeners also ask themselves what might go right. Yeah. What would happen if this was the best choice that I ever made? I love it. Well, Simone, thank you. This was so great.

58:02Simone Stolzoff: Thanks for having me. I appreciate it. Whoa. That was a really fun conversation. That was a lot of tools. That was a lot of different ways to think through what it is that you really want out of work, which I'm psyched about. And I really hope those tools help some of you. I just want to revisit one of them because I'm still just, it's like stuck in my brain like a brain worm, which is those three questions. What do you want? Do you want to want that? And what does that choice say about who you are? Those questions are nutty. I just want to name that because they are very big. And like I said in the episode, they are kind of judgy.

58:46They're asking you to evaluate what is underneath the motivation for something. And I honestly, I wish I'd had those questions and some decisions in my life because sometimes that just feels like there's this force tugging you that you almost can't say no to or there's this inertia or momentum that's like dragging you towards something. And often that actually isn't very healthy, like at least in my experience. And you need a question or you need a moment to like slap you and be like, why? Why do you want this? Like, why are you going back to this unhealthy relationship? Or why do you want this job that you kind of know is going to be bad for you?

59:22So anyway, I loved those questions, even if they're kind of blowing my mind a little bit. But I love the last one in particular, and I really loved Simone's point about The fact that like fundamentally what you are asking is what do I want my life to look like? And, you know, the question, the third question is what does this choice say about who you are? And his point is like, who do you want to be in the world? Is the highest order question because work is a part of that, right? But it's not all of it. And there's a lot of different ways. I think his point about the good enough job is there's a lot of different ways that work can serve you in whoever you want to be in the world.

1:00:01Oh, man. I just want to name, too, that it is hard sometimes to figure out what you want. Like I said, I am often better at knowing what I don't want than what I do want. And it's why I wanted to start here for this series. It isn't always about knowing exactly what the right path is and exactly what it's going to look like in 10 years. It's really often just how can you get to moving forward from being stuck or from being unhappy. So I loved that. So we started here. Now we have some tools that help us know what we want at work. And next week in this series, we're going to say, okay, now we know what we want at work.

1:00:35How do we ask for it? How do we get up the courage or the clarity or the conviction to go ask for what we want, whether it's from the world or from our boss or from our work as a whole? So I'm excited to do that with you next week. And I'll talk to you all soon. Thanks for listening to Work Life. If you like the show and want more, hit that follow or subscribe button so you don't miss an episode. and share any episodes you love with a friend or leave a review wherever you're listening to this. Work Life is a production of Ted and Pushkin Industries. This episode was produced by Daphne Chen. Our video editor is Connor Titsworth.

1:01:13Ban Ban Cheng is our story editor. Mixing by Hansdale Shi. Ted's executive producer is Daniela Balarezzo. Constanza Gallardo is the executive producer for Pushkin. Special thanks to Roxanne Hilash, Valentina Bohanini, Lainey Lott, Tansika Soongmanivong, and Ashley Murphy. I'm your host, Molly Graham.

1:01:38This episode is brought to you by Founders Mentality, a podcast in partnership with Bain and Company. If you listen to Work Life for conversations about leadership, navigating change, and unlocking innovation, I have another show for your rotation. It's called Founders mentality, the CEO sessions. It gets into the real decisions behind some of today's leading executives and companies, not just what a CEO should do, but who a CEO has to become to do it. In their recent episode with Laura Boro, group CEO of The Economist Group, you hear how she walked into a divided organization and a transformation project that had already cost the company millions and made the call to scrap it.

1:02:18Instead, she pushed for a new approach, one that could fund itself and bring the business back together. She and host Jimmy Allen break down that choice, how customer data reshaped the company's priorities, and how The Economist is thinking about transformation now, in the age of AI. Follow Founders Mentality The CEO Sessions from Bain & Company, wherever you get your podcasts.

1:02:43Simone Stolzoff: Being a serious business owner takes hard work, patience, and a drive to keep moving forward. So it's important to find a serious business card that goes the extra mile. With the VentureX Business Card from Capital One, you earn unlimited double miles on every purchase. And with big purchasing power, you can spend more and earn more. This is your sign to take your business to the next level. The Capital One VentureX Business Card. What's in your wallet? Terms apply. See CapitalOne.com for details. Hey, we're Nick and Jack, hosts of The Best One Yet. Behind every episode, there's research, email, spreadsheets, and our shared Google Doc, the Headline Hammer.

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