The right risks to take for a great career (w/ Molly Graham) (video)

Molly Graham has had a high-powered career at a ton of extremely successful companies—and now she’s joining TED as the new host of the podcast WorkLife with Molly Graham. So what does it take to have a great career? And how do you know what job you should take, which you should quit, and which you should try to change? Chris and Molly discuss career transitions, the benefits of taking a meandering path, and how to take more risks for a fulfilling life. Featured guest Follow Molly Graham on Instagram https://www.instagram.com/molly_graham/, LinkedIn https://www.linkedin.com/in/mograham/, and on Substack https://mollyg.substack.com/Learn more about Molly's Glue Club https://glueclub.com/! Listen to WorkLife with Molly GrahamWatch Molly's TED Talk https://www.youtube.com/watch?v=amtBUvkweEA Connect with the team Follow Chris on Instagram https://www.instagram.com/chrisiduffy/?hl=en and at chrisduffycomedy.com https://chrisduffycomedy.com/Buy Chris’ book, Humor Me https://t.ted.com/ZGuYfcL Watch How to Be a Better Human videos on YouTube at TEDAudioCollective https://www.youtube.com/TEDAudioCollectiveFollow TED on X https://x.com/TEDTalks, Instagram https://www.instagram.com/ted, Facebook https://www.facebook.com/TED, LinkedIn https://www.linkedin.com/company/ted-conferences/, and TikTok https://www.tiktok.com/@tedtoksFor the full text transcript, visit go.ted.com/BHTranscripts https://go.ted.com/BHTranscripts Hosted on Acast. See acast.com/privacy https://acast.com/privacy for more information.

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:01Chris Duffy?

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• 0:48Speaker 01

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• 1:33Speaker 01

  which flags issues in real time, and Navigator, which figures out why those issues are happening and what to do next. It's secure, scalable, and built to serve the customer. When AI works well, it shouldn't feel like AI. It should feel like you're being seen and heard and valued. Unhold your customers with Parloa. Learn more at parloa.com. That's P A R L O A dot com.

• 2:03Chris Duffy?

  This is How to Be a Better Human. I'm your host, Chris Duffy. Today on the show, our guest is Molly Graham, and Molly is, among many other things, a very successful businessperson, a writer, and the new host of Ted's Work Life Podcast. So we're going to be talking to her about how the rules for building a great career have evolved and what it takes to navigate this new work landscape. You know, when I was searching for my first job, I really, really, really wanted to write for a newspaper. I was positive that I wanted to be a traditional newspaper journalist. But then everywhere I applied, they were cutting positions rather than hiring. I couldn't get a job, and I needed a job that would let me pay my bills. So I just started applying for anything and everything. And I ended up getting a position teaching English abroad.

• 2:44Chris Duffy?

  And then I got a job teaching at an elementary school in Boston. And I could never, ever, ever have predicted that starting there would lead me to be here hosting this podcast and talking to you right now. In fact, one of the biggest lessons that I've learned, maybe the only career lesson that I feel totally confident standing behind, is that you cannot predict how things will turn out. Like it or not, you are going to be surprised. So how do you help people to figure out how to navigate a career path if you can't possibly know what's coming next? Well, that is exactly the kind of challenge that Molly lives for. To get us started, here's a clip from Molly's TED Talk where she's addressing one of the biggest misconceptions that people have about their jobs and their career choices. Here's Molly.

• 3:26Speaker 02

  There's a lot of pressure around what it takes to build a great career. And it all comes back to this idea that you're supposed to know what you want to do. It's an idea that I like to call the stairs. Here's how the stairs go. You show up in college, and you're supposed to know what you want to major in. That major is supposed to lead you to your first job. And then you get another job, and you get promoted and promoted and promoted forever. The best part about the stairs is safety and security. It feels like you know what you need to do to get ahead.

• 4:08Speaker 02

  The worst part of the stairs is that it's like a weird video game that you can get stuck inside of for years. The stairs will make you feel like your self-worth is tied to your title, or your last performance rating, or your next promotion. But the truth is that the stairs are an illusion. These days, excellent careers are not built by excellent stair climbers.

• 4:37Chris Duffy?

  Okay, we're gonna figure out how to get off the stairs and into a great job, or a great series of jobs, right after this break. But first, my job includes the requirement of reading you these podcast ads.

• 4:53Chris Duffy?

  This episode is brought to you by Planet Visionaries, a podcast in partnership with the Rolex Perpetual Planet Initiative. What connects a hidden laboratory in the Amazon, giant pandas in China's mountain forests, research relating to the ocean, and communities living alongside wildlife in India? That's what you'll hear on season six of Planet Visionaries. Stories from the explorers, scientists, and conservation leaders whose work addresses research, biodiversity, and conservation issues in specific locations. Planet Visionaries, hosted by environmental advocate and professional climber Alex Honnold, brings you real stories of discovery, determination, and research and initiatives relating to environmental change.

• 5:36Chris Duffy?

  In partnership with the Rolex Perpetual Planet Initiative, this is Planet Visionaries. Listen or watch wherever you get your podcasts.

• 5:46Speaker 03

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• 6:44Chris Duffy?

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• 7:26Chris Duffy?

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• 7:45Chris Duffy?

  And we are back. We're talking with Molly Graham about how to build a great career, whether you are just starting out or you're many years in.

• 7:52Speaker 02

  Hi, I'm Molly Graham. I'm the new host of Ted's podcast, Work Life. And I'm also a company builder, a writer, a community builder, and some other things that I'm still trying to figure out.

• 8:06Chris Duffy?

  Well, Molly, I'm so glad I'm getting you to talk to you, not just because we are in the Ted siblings now in the podcast world, but also because I think you do such interesting work and you think about work in such an interesting way. And especially for me, a person who's like never had a corporate job, right? Like I worked at an elementary school and then I was a comedian and now podcasting. Like none of these are like regular, traditional hierarchy. So I love the way that you talk about a world that is for me like largely foreign in.

• 8:38Chris Duffy?

  And make it so relatable, but also you take those lessons that I know are really practical for people who are working in traditional work environments and also make it practical for people like me who are not in traditional work environments.

• 8:47Speaker 02

  Well, first, thanks. That's very nice. And second, I'm so fascinated by your path, too. Just like you've done such an interesting job defining like what, uh, what moves you and what feels right to you. And that to me is like the most interesting quest in work.

• 9:03Chris Duffy?

  Well, if people are following me into the wild blue yonder, we all are doomed. So that's my number one takeaway, but I will take the compliment. And let's look at this concept from your TED Talk, which is you talk about this concept called the stairs. So can you tell me a little bit about what the stairs are and why you believe that's a career model that we should maybe have in mind as we're thinking about how our career could be going or maybe should be going?

• 9:28Speaker 02

  Yeah, for sure. I mean, I think the stairs, like, I think a lot about folks graduating from college. And I think there's a lot of panic around like finding your first job. And, and this sense that if you don't get it right, then you're on the wrong path forever. And, you know, we could talk about first jobs a lot, but, but part of the point of like, I think what happens when you, you do get that first job is you, you end up on this, this set of stairs that you didn't even know existed. And, and the idea of the stairs is basically like, it's kind of like our parents' generation, like, at least my dad, like, he, he worked in the same place for 40 years. I feel like when I left my first job, my dad was like, you, you're doing what? Like, you're leaving, you're leaving a job? You know? And I, so many of my friends have the same thing with their parents where their

• 10:11Speaker 02

  parents did the same thing in this, you know, they might've done different jobs in a, in a company, but they were in the same company. And this is actually a picture someone drew on a whiteboard for me, um, uh, way back in the day where he was sort of like, look, you can stay in the same company and you can walk up these stairs. And, and, and it does have kind of a rhythm to it when you're in these bigger companies where like every two years or three years, you get promoted and your job changes from manager one to manager two. And you end up having this sense, or at least I think that all corporate, you know, compensation systems are, give you this sense of like, if I just keep going up these stairs, somewhere up there is like this. Pot of gold, or like this award or this medal.

• 10:55Speaker 02

  But in theory, it's like methodical, straightforward. But it's also like, both like extremely boring in lots of ways where like, I think you can get very stuck in sort of their version of what is successful and what is good. And also, in a lot of cases, it doesn't always give you the chance to test yourself. But yeah, that's, that's the stairs.

• 11:16Chris Duffy?

  You know, it's interesting, because I think for a lot of people, especially coming right out of, of college or high school, right? There's such a set vision of what success looks like, right? You go to school, you submit your work, your work is graded, there's a clear sense of what a successful grade is, what a failing grade is. You got 100 on a test, you got a 90 on a test, you got an 80, those all mean really clear things. And then we get into the work world and we want, at least a lot of us really want that same kind of clarity of what success looks like. Like, what is an A at my job? What is an A plus at my job? What's an F at my job? And I think it's really challenging for a lot of people to realize, like, that's just not how the world outside of school works as much. There isn't one set definition of success.

• 12:01Speaker 02

  Totally. And, you know, imagine, imagine that for comedians, Chris. Like, what is an A? You know, what is an F?

• 12:08Chris Duffy?

  Totally. You know, what I think, honestly, when I talk to people, especially people who are not already in performing arts and want to be, the hardest part about it that I think is hard to grasp before you do it, is that there is no promotion in this job, right? Like, your job title is comedian, and the difference between when you are a completely terrible comedian and not making a single cent and not making a single person laugh, and when you're hugely successful, it's still the same title. And so you don't ever have like this clear, I've advanced to the next level. It always feels like much murkier than you think it might from the outside.

• 12:46Speaker 02

  Yeah, totally. And I- I really think like from, from the moment you step out of college and whatever, you know, framework that is today for forever, there's always this sense of like, oh, someone has the answer and I just need to find it. Do you know what I mean?

• 13:02Chris Duffy?

  Totally.

• 13:03Speaker 02

  Like someone else, I just, if I imitate that person or that's, you know, and I always say, it actually often feels like there's just like a door that if you could just like get behind the door, then everything will make sense. But then one of the things that happens in life is you like, open a door and you like walk through it and you're like, oh shit, there's another door. Do you know what I mean?

• 13:21Chris Duffy?

  Yeah.

• 13:21Speaker 02

  And it's like this never ending set of doors, you know, obviously that becomes then like, what is success? And you know, I always, I think about this a lot for like, you know, so much of the goal in the world of Hollywood and whatever is like, oh, win an Oscar, get this award, whatever. And I'm always like, yeah, but then you win an Oscar and then it's like, but then I need to win another Oscar. Like, it's like all these doors that again, you get through it and you're like, but I'm not, you know, I'm not Julia Roberts or I'm not Meryl Streep and like, am I successful? And I think eventually you really have to like face down that question of like, what is successful to me?

• 13:54Chris Duffy?

  There's an interesting thing where I think the difference between like, meaning and value and success, and I would probably put quotes around success because it's like, what do we think of as success, which often just means like making money or having a particular title. And those actually aren't very often very meaningful or bringing a lot of value to your life. Because like you said, you get there and then it's like, well, well, what actually comes next?

• 14:19Speaker 02

  You know, I think of those as kind of external definitions of success, meaning they look successful to other people. And I think when I was early in my career, that is how I thought about success. I was like, I'm just gonna crush this stuff and get promoted and other people will, it matters to me what other people think of me, right? It matters to me that, that I've proven myself, like I've proven myself that I'm good. But a lot of it was like proving myself to like all the people around me that I was good.

• 14:44Chris Duffy?

  Yeah.

• 14:44Speaker 02

  And, and you know, that did come in the form of these externalities. And then I think I, like so many of my friends, hit a moment where I had the title or I had the job that I kind of like thought I wanted. And I was like, uh oh, like I have this friend that tells this story, I actually told it in the TED Talk where she's like climbing this ladder and literally gets to be CEO and then goes, is this all there is? You know, like I'm, I don't like this. And it's like, well, then what? You know? And I think there's just these moments when. You get out of that sort of I'm proving myself phase and you have to really ask like, okay, what is my definition of success, you know, and to your point about meaning and value, what matters to me?

• 15:28Chris Duffy?

  Okay, so we've already opened up so many of the threads that I want to chase down during this this conversation. And one of them is, you know, we talked about the stairs, the flip side, the other way of approaching a career that is a framework that I learned from you is that this J curve, the idea that we we get somewhere and then we jump and it's kind of we jump off a cliff. We go backwards in some ways in our career in terms of like, it doesn't feel like we're making progress. It feels like we're getting worse. It maybe feels like we're making less money, but it can lead us to an entirely new place. So can you talk a little bit about what the J curve is and then a little bit about how that has guided you in your own career decisions?

• 16:05Speaker 02

  Yeah, totally. So this is something I experienced really intimately when I was, I spent five years at Facebook and I spent the first two years in HR and recruiting, helping sort of figure out who we were and how we wanted to talk about, you know, why you should come work at the company and what kinds of people belonged. And then I think I did well in that. And so somebody came to me and said, do you want to come help me build a mobile phone? And I was like, first of all, why are we doing that? That sounds like a terrible idea. But then second of all, I was like, why are you asking me? Like, I'm highly, highly unqualified for this.

• 16:47Speaker 02

  But then I was just kind of like one of those ideas I couldn't put away. And I remember this conversation with a friend of mine where he said, like, you've proven you're really good in HR and these were like really big, like complicated company-wide projects. Why don't you go see how actually good you are? And and it was this like, oh, like, I'm gonna go figure out if I can do this. And this was the moment, by the way, when the person, the guy that was trying to hire me and get me to come work on the phone, drew the stairs for me. And he was like, basically it was him being like, you can be boring and stay on these stupid stairs, or you can jump off a cliff with me. So it was like, that was his pitch. And he was like, the most interesting careers are built by people that are willing to throw

• 17:29Speaker 02

  themselves into something that they might not be good at, that they might not be successful at, because it, you basically buy this like incredible learning curve about yourself and about the world. And so I bought in. I was like, okay, let's see. And I, I went to work on this mobile phone project, knowing absolutely nothing about phones or the mobile industry or anything. And I immediately just felt like the dumbest person in the entire world. Like I was sitting in rooms with just, oh my God, the smartest people, uh, asking the stupidest questions, you know, and I felt embarrassed. I felt like an idiot. I felt like I didn't know what I was doing for really six to nine months,

• 18:08Speaker 02

  but slowly I learned, I mean, I learned so much. I think it was unclear for a while if I was like ever gonna feel competent, you know? And I was just talking to someone who just did this and she was like, I'm three months into it and I still feel like I only know what I'm doing 30% of the time. And I was like, you're on track. Like, give it, give it three more months and you might have a moment where you feel competent. Cause that's what happened to me. Like six months into it, I think it was like six, might've been nine. I flew home from Taiwan where I had been working with hardware manufacturers and I drew the hardware layout for a mobile phone on a whiteboard for my boss. And I was basically explaining to him why something that he wanted to have happen couldn't happen, but I explained it to him like very precisely. And I remember him looking at me being like,

• 18:50Speaker 02

  whoa dude. And me sort of having this feeling of like, oh, I actually know things. And that was the moment of what, you know, so for me with like with jumping off cliffs or the J curve, like you basically fall, you hit the bottom and then you start to climb out. And that feeling of like, oh, I'm someone different than I was six months ago because I have all these skills and all this knowledge, but it also like, I have a different level of confidence all of a sudden. Like I can do things that I didn't know I could do. And for me, that phone, uh, project, which I was then on for three years, which by the way, was a giant failure. So like, yeah, the project was a failure, but it was not a failure for me. Like I, I learned so much about myself, good and

• 19:33Speaker 02

  bad. But the most important thing it taught me was that I love. That kind of learning and that I really, I now say like, I only take jobs that I'm highly, highly unqualified for. When someone offers me a job I know I can do, I'm like, that sounds boring to me.

• 19:49Chris Duffy?

  Well, so yeah, this is something that I wanted to, to, to talk about because I think a lot of us limit ourselves because we're so worried that we might fail and that that would be actually a terrible thing as opposed to realizing that that is the path to getting better at anything, almost failing over and over and over again.

• 20:04Speaker 02

  You know, someone posted this, uh, quote, they posted a statement when I, my TED Talk got posted and the person said, you know, people think that you have to be confident to act. And the truth is confidence comes because of action. You don't have to be confident in order to act, or if you wait for confidence, like you just might be waiting a really long time. But for me, like actually one of my greatest strengths is being kind of an idiot and asking a lot of dumb questions and being able, you can put me in literally any situation in almost any business in the world and I will be able to learn it. And I don't think

• 20:44Speaker 02

  most people have the confidence to say they can do that. You know, so the only way you learn these things about yourself, what you're capable of, what you're really exceptional at, um, is by trying. And part of trying is failing, right? Like one of my phases at Facebook on this phone project was somebody, I think the last phase, Mark asked me if I wanted to be the product manager for it. Cause prior to that, I was sort of like in partnerships and hardware and operations. And he was like, do you want to be the product manager, which is sort of the person that runs the whole project. There was something inside me that said, like, that doesn't sound like fun, but I was so confused at the time that I was just like, sure, it's the job that everybody inside of a tech company wants.

• 21:25Speaker 02

  So I'll be the product manager. Just FYI, no one should ever hire me to be a product manager. I was like, it was like really learning, like, oh, I both like hate this and I'm really bad at it. So like, it wasn't all wins, but it was this like incredible journey of self-discovery.

• 21:42Chris Duffy?

  Okay. We're going to take a quick break, but then we will be back to discover more about Molly and ourselves. Don't go anywhere.

• 21:56Chris Duffy?

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• 22:38Speaker 01

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• 22:57Speaker 01

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• 24:29Chris Duffy?

  And we are back. For me personally, when I left my job as a teacher and when I was leaving the fifth grade classroom and I was going to start trying to make a living in comedy and radio and podcasting and all of that, it felt so much before I did it, like I was about to jump off a cliff. Like, I am going to make this giant leap. I'm going to leave a really stable, predictable, reliable job, and I'm going to do something that is very uncertain, where I have no idea if I'll be able to make enough money. I have certainly no idea if I'll be able to continue this career for five or 10 years. And then as soon as I did it, I remember so clearly, like truly the week after I left the job, where I was like, I'm no longer employed by the school anymore. I no longer felt in any way like I had jumped off a cliff.

• 25:14Chris Duffy?

  And instead, I had this clear, like, alternate metaphor that I had turned a corner, where it was like, oh, I could go back. It's like, I turned and I could go back. I just couldn't see where I was going. And so because of that, it felt like this dramatic leap. And I think sometimes we make a career decision that is a true, like, you've jumped off a cliff. But a lot of times, it's not so true, the story we tell ourselves that like, you could never go back to the job that you left or the field that you left, you know? Like, if you are a lawyer and you've gone to law school and you have your credentials and then you quit to become a novelist, it's not like you can't get another job as a lawyer later on. Like, that's actually not forbidden.

• 25:49Speaker 02

  Yeah, Amazon has this idea of one-way door and two-way door decisions. Like, it's one of their decision-making frameworks. It's actually kind of helpful in life because... The idea of a one-way door is a decision you can't take back. And the two-way door is a decision you can take back, you know? And the point of the decision-making framework is just like, treat one very differently than the other, you know? You know, like if you try something and you fail at it in one form or another, often there is a safety net there in some form or another. I think it doesn't always feel that way, you know? Like, I mean, particularly maybe these days, like, people are scared about whether jobs will exist and things like that. So it can feel extra scary to take a risk, to quit and become a comedian. But I'm curious, like, in your experience,

• 26:33Speaker 02

  what made you feel safe enough to take that risk? Because I do think there's different kinds of fear. And there's like the fear I might fail. And then there's like the much more existential fear of like, I'm not going to be able to feed my family. So what do you think let you take that risk?

• 26:47Chris Duffy?

  Two, two very clear things. One was, I did the math and I realized that what I was currently making, teaching improv and doing a few comedy shows, if I just kept that stable, and then my worst-case scenario, if I kept that stable and then I worked half-time as a barista, like if I just got a job at a coffee shop, and I was like, that's not what I want my other half of my time to be. But if I get half the time working at a coffee shop and then I'll still have more time to do comedy and creative stuff. And I just keep all my creative things the way they are now. Between those two things, I will be able to pay all of my bills. So I just did the math and was like, okay, that's the financial goal is just to like not, you know, not go into a deep debt that I can't get out of. And the second one was, I talked to the principal before I left.

• 27:31Chris Duffy?

  And I said, if I quit and try and pursue this, which they were very supportive of, like the other teachers liked coming to my shows. And like, they, they saw potential in me, which was very.

• 27:41Speaker 02

  I can only imagine what kind of teacher you were. You must be so fun.

• 27:44Chris Duffy?

  Not good at classroom management, very fun, but very bad at discipline. That's the number one thing. But what they said is, I said, like, if I leave and it doesn't work out, can I come back? And she said, some version of, you know, we can't guarantee anything, but we hire teachers every year and we like you. So I think you'll probably have a job here in the year after September, if you don't, if you don't come back. So I felt like, okay, I'm making a one-year decision. And I'm pretty sure that my worst-case scenario is I just kind of, I dip a little into savings, but mostly just stay like neutral for a year. So that's, that's what it felt like.

• 28:17Speaker 02

  Those are like such great examples for two reasons. Like, one is.

• 28:22Speaker 02

  I think financial fear is such a powerful force for people. It's one of the reasons, by the way, that I hate student debt. I think it's one of the greatest sort of like risk quashers in the world. But, you know, I always say there's a difference between diffuse financial anxiety and specific financial anxiety. And I think a lot of people stay stuck in diffuse financial anxiety, meaning I'm scared I won't have enough money. But what you did is what creates specific financial anxiety. Basically, I know how much money I need every month to live the life that I feel good living. If I have savings, like I know how much I'm willing to spend in order to be able to take this risk. That just changes it from like, I'm scared I'm not going to be able to feed myself or my family or my cat to like, I have to be able to make this much every month.

• 29:07Speaker 02

  Like, what are different ways I could do that? Which is exactly what you did, you know? And I, whenever I work with folks that are thinking about taking a risk or leaving a job or whatever, that is what I do. I'm like, let's sit down, let's make a budget, let's like get to a number and then let's talk about what you have to believe to be true to take a risk on this number. Like, can you consult and get this much money a month? Like, the kinds of things. And often the number is just actually a lot smaller than people think it is. I mean, there's so many different kinds of risk in life. And I think if you can't take a big one, sometimes you can take a small one. But the big risk, sometimes people do feel very much like it's a, there isn't a safety net, and that can be really scary. I mean, I think one of the things that you have to learn if you want to push yourself

• 29:51Speaker 02

  to, to sort of be able to find your boundaries and, and also I think your genius is like, fear does not mean you shouldn't do things. Yeah, you might fail, but what if you don't? What if you succeed? What if you're better than you think you are? What if this thing leads you to something that you can't imagine? And, and for me, that's, that's been the case where, you know, I've certainly failed a lot, but I've also found things that I like could not have possibly imagined where I was qualified for a job or I, you know, built a relationship with someone that if I hadn't taken the risk, I would never would have known, you know?

• 30:26Chris Duffy?

  I want to read something from your newsletter, which I really loved and I think it's a lot in line with what we've been talking about. One, my basic belief is that happiness at work is fundamental to high performance. Yes, I have wonderful friends who perform incredibly well in misery and anxiety, but I don't believe it is healthy or sustainable for anyone to do that over a lifetime. In fact, I believe it takes years off of your life. I don't know that I'm right, but it's what I believe and it's certainly how I manage my choices and what I optimize for. And two, it is really important to understand that making money has not been a primary motivator for me in my career, mostly because I'm very lucky. That absolutely changes the equation for how you decide what to do with your time and I think what work means.

• 31:08Chris Duffy?

  So my question for you is, how do we know when we're in one camp or the other? Is it actually just as simple as doing a spreadsheet? And then the second question is, if you want to be happy at work, any work is going to involve periods where you're unhappy with the job or frustrated or feel like you're not good at it. So how do you know when you're happy at your job? How do you know when you found a job that will make you happy? So how do you know when you're financially stressed? Or you actually have the ability to make a choice? And how do you know when you're actually happy?

• 31:37Speaker 02

  So I think like, why do we work? The first answer is to have enough money to support ourselves and our family and to live a life that we want. And for a lot of people, that is the first and primary answer. There is like Maslow's hierarchy of needs, right? Like, I gotta make sure I have food. And, you know, work is a huge piece of that for a lot of people. But I do think that I've just seen a lot of friends sort of blindly follow that motivator, right? Money. And I mean, the inverse is also true, which is that you can design a career where you're never gonna make money.

• 32:20Speaker 02

  I mean, you're an artist on some level and you've seen a lot of friends, I'm sure, struggle with the relationship between what they feel like they've been put on earth to do and what they can make money doing. So I always say that the- The true sort of like version of your craft is like the things that you love doing, the things that you're great at, and then the things people will pay you a bunch of money to do. You know, that's the happiest Venn diagram in the world. But I think that money is a real factor. And until you feel financially taken care of or financially safe, money can often be the sort of big red light, you know, that's stopping you from taking risks and things like that.

• 32:58Speaker 02

  The trap for me is I've really watched a lot of people and friends let that guide every decision without asking questions, right? Without questioning their own happiness relative to money. And I think we're each programmed differently. We come from different families. We come from different parents and, you know, I have a ton of friends that are the kids of first generation immigrants or the first generation immigrants themselves. And I always ask that question when I'm talking to someone about this stuff because I think if your parents like moved across the world to take care of you and, you know, often they taught you that like you just got to earn money.

• 33:38Speaker 02

  Like you gotta like be on this treadmill for, you know, and that that is the purpose of work and no one cares about how you feel. And that programming can be very hard to shed, you know? Like how, when will you feel safe? Is there a world in which you'll ever feel safe? You gotta have an answer to what enough is and when you'll feel safe enough to take a risk or to demand happiness, you know, to demand that you should love at least most of your work. Because like work is a lot of time. Like if you let it go by, it's your whole life. If you literally do the math, like it's most of the hours in your life for most of us. And to do that and be miserable or anxious or, you know, all those feelings like for most of your life,

• 34:23Speaker 02

  like, how can it not affect your health? Like, we now have so much data that says that it does. And I think that question of safety and what's going to make you feel safe, like that's wildly different for everyone. Like, I don't, that's not a prescriptive thing. That's not like, oh, you hit this net worth and everyone feels safe. Like, no, it's like you hit this dollar amount per month. And some people are like, I still don't feel safe. But I think. You have to tackle that question at some point because otherwise you can spend a lot of your life really unhappy. I, the one thing I would say about happiness is that like, yeah, everyone's miserable at some point at work, like, but I have this strongly held belief, which, which, you know, is not mine.

• 35:03Speaker 02

  It's anybody that works in sort of the strengths-based work or the sense of like that you are at your best when you're doing the things that you're sort of uniquely great at and that that give you energy, that that's the, the highest and best use of you in the world. When I do work with people to ask them to like, kind of think about how they want to shape their future or what they might want to invest more time in or explore next, a lot of what I'm doing is looking back over what they've done and asking like, when did you feel like sort of most alive? When did you feel most energized? When did you feel like the time flew by? When did you feel like, you know, I could do this forever? Those are the signals to pay attention to, to think about like, what is the kind of work that really can bring you joy? I like to say that my goal is that I'm happy 90% of the time at work. And like, I do that today.

• 35:47Speaker 02

  I'm so lucky and I feel like so grateful because that was not true for a long time.

• 35:52Chris Duffy?

  I think also expanding the, the timeframe you look at it on, right? Like if your goal is that I'm going to be happy every minute and that if I have an unhappy hour, that means like something has gone horribly wrong at work versus if it's like, okay, like you may have a really rough month and that actually doesn't mean that your career or your job needs to get completely tossed out. But is it like struggle where you're learning something, where you're growing? Or is it struggle where you're getting like abused and beaten down and dismissed? Like those are really different versions of a bad month.

• 36:20Speaker 02

  Yeah, there's such a difference between being deeply uncomfortable and very stretched and being miserable. I burnt out at Facebook. I, you know, after a very intense five years, I like really had physical symptoms of could not keep going. And I remember this woman who worked in HR at the time. She said to me, you know, everybody has peaks and valleys at work. Like, there's no such thing as like, everybody being like, happy all the time. And she was like, so you're happy some of the time and you're less happy some of the time. But the goal is obviously like, more peaks than valleys. And, and also that the valleys aren't super long. And she looked at me and she goes, your valleys are getting longer and closer together. You know? Which, which I think about a lot because it's like, you know, that's measurable. I had a coach when I was sort of struggling with a job who said,

• 37:03Speaker 02

  you know, at the end of the day, I want you to go through every single meeting that you've sat in and rated on a scale of one to 10 and do it for a week. And it was like, eye opening because I had 10s and 1s, you know, sitting right next to each other. And it mostly taught me a lot about the kind of things that do bring me energy. But there's a lot of exercises you can do to kind of really ask yourself, like, what? Are you uncomfortable? Are you miserable? How much? Like, what is bringing you joy? Can you do more of that? Like, that's, that's something you can micro optimize as much as like, needing to quit a job and go do a whole other thing.

• 37:36Chris Duffy?

  You just recently started this new role as hosting the Work Life Podcast. How did you think about whether to do it or not? And what were you worried about? Or what were you excited about?

• 37:49Speaker 02

  So I got asked to take over this podcast. And it's obviously just such an amazing podcast. It's been, you know, Adam Grant has built over the last seven years with TED. And a lot of people listen to it.

• 38:03Speaker 02

  And when they first called me, they sort of said, you know, have you thought about podcasting? And I was like, yes, and do we need more podcasts in the world?

• 38:11Chris Duffy?

  And they're like, great news. This is conservation of podcasts. A podcast will neither be created nor destroyed. It will simply move from one form to another, like water to vapor.

• 38:23Speaker 02

  And then they explained what they were curious if I was interested in. And I tell you, Chris Duffy, I, I said yes on that call, like, five minutes after it. And I'll tell you why. Because they offered it to me. And my first reaction was, holy shit.

• 38:41Speaker 02

  I have no idea if I can do that. And I think I'm like, I'm terrified. And I'm like, why are you offering this to me? And I'd never done audio. I mean, I've been on other people's podcasts, but I've never done, I have never done video. I don't know anything about this world. Like, I don't know how. So anyway, spiral. But, you know, immediately for me, all of those signs are like, you have to do this because you're scared. And you don't know if you can do it. And what an incredible learning opportunity. And I had to, you know, when I took a step back from that first call and sort of had a chat with myself, it was like, okay, if we're gonna do this, like, our bar cannot be Adam Grant, or Amy Poehler, or Chris Duffy. Like, I, this has to be-

• 39:25Chris Duffy?

  It can be one of those three. Let's be real.

• 39:28Speaker 02

  No, I mean, you know, there has to be a different way of measuring success for myself. And so I made an agreement with myself that I was gonna measure success on two things. The first was that I was gonna learn so much, right? That by the end of, you know, even one year of doing this podcast, that I was gonna be a different person. I was gonna know so many things that I hadn't known before, including all the things that I screwed up. And then the second thing was that I was gonna make some stuff that I was proud of. And that I wanted to be out in the world, that I was gonna put content into the world that I just knew could help one person.

• 40:07Speaker 02

  Right? And, and that's actually how I thought about my TED Talk, too, because, I mean, you know this, like, TED is kind of a terrifying experience as well. And there's a very like, visible like, number next to your talk and all these things. And I think if you get caught in that game, which is the external validation game, right? Like, you know, how many people have watched this thing? It's not how I measure value. And I really, you know, when I do stuff like this, it's terrifying. And it's so easy to get swept up in these sort of like, external- Signals of success, I have to say no. What matters to me is that I get one email from someone that says, thank you so much. This made such a huge difference in my life. And so that's all that matters.

• 40:49Speaker 02

  You know, that's my definite, as I go on this like absolutely terrifying journey that I'm like, let's go watch Molly make public mistakes. And a lot of people be potentially frustrated that I'm not Adam Grant. Like, I want to make stuff that I'm like, no matter what, I'm glad it exists.

• 41:03Chris Duffy?

  I love the, the concept of like defining success in not just every possible form, because it really does get out of hand. I mean, I, I've had this so many times where it's like, if I ahead of time think, what do I actually care about? What do I care about on this project? It's much easier to then go in to a job or a project or anything that I'm doing and say like, okay, this is what I'm aiming for. And it's nice if the other stuff happens. It's not like I don't like the other stuff, but, but my goal is this one thing.

• 41:30Speaker 02

  Yeah, well, and it's to the original, you know, the thing I said a little bit ago about the doors. Like, it's actually pretty easy to feel like a failure. Do you know what I mean? Like, it's, if you look in the world and you're like, uh, there's a million definitions of success that, you know, are unachievable, or at least like gonna make you feel like you haven't done anything. And that can be subscriber counts, that can be view counts, that can be such and such awards, that can be so and so's getting all these jobs and getting these offers that I'm not getting. Like, I spend a lot of time being like, I'm not that person, therefore I have failed. I optimized for that stuff. And then I found myself in a place where I was like, oh, I'm miserable. Like, I don't like this. Like, I have, I have fought for other people's goals or other people's definitions of success,

• 42:14Speaker 02

  and I have discovered that land and it is not for me. And so like, I think as I embark on, you know, taking on work life and just a project like this, like, I think I have to have a compass that works for me. And, and I have to know, um, what is good enough for me? Because otherwise I'll drown in like all the comparison and all the sort of things I'm not. And that's just not a good use of like my time or energy.

• 42:43Chris Duffy?

  I feel like the title of this episode is something like, how to chart a career path, or how to chart a career path that you actually find meaningful. You have a great essay about early career advice. Is it possible for me to just have you read some of that essay right now?

• 42:58Speaker 02

  All right. I've never been one of those people who knew what I wanted to do for work. You know, those people, the ones who've known they wanted to be a doctor since they were 14? In college, my best friend knew she wanted to become a paper conservationist. That's not someone that recycles paper. It's someone that restores and maintains old documents. And that's what she is today. Cut to me, who majored in African history in college, but ended up in tech. And my first job out of school was leading wilderness trips in Patagonia and Alaska. My parents were very unsure that that was a real job. There is some cultural programming and family programming telling you that as a 20-year-old, you should know what you want to do. I know I felt that way, and I see it in my younger friends as they head off to college.

• 43:42Speaker 02

  But over my 20 years since college, I've become a big believer in the winding path as a powerful way to figure out the highest and best value you can bring to the world. I want to make the case that not knowing is not only okay, but that it can actually be a strength if you're willing to lean into it and use the first part of your career to learn about yourself. It's a different, and I think better, way to do your 20s. Figure it out mode. Eventually, you want to find the jobs and situations where it's full of the stuff you are great at, the stuff you love doing and also the world highly values what you have to offer. To start that winding path, you have to use your 20s to collect data about yourself.

• 44:22Speaker 02

  That means you get to those bigger answers by 30 or 35, not by 25. To be honest, I'm a general believer that some amount of exploration is good for anyone, even those of you that are like my college best friend and feel sure of what you want to do. I'm thinking of the friends who made it all the way through medical school and got to residency only to realize they didn't want to be doctors.

• 44:43Chris Duffy?

  You're incredible at reading things out loud. Great voice.

• 44:46Speaker 02

  That is not true. Just ask my producer on Work Life.

• 44:50Chris Duffy?

  Okay, well, I'm impressed. That idea that we shouldn't necessarily know exactly where we want to be and that even if we do know exactly where we want to be, we should still embrace the potential to explore and to discover new things about us. I find that so relevant to how I think about my own life and to the people whose careers I admire most. And honestly, I would say like, not just till you're 35. I'm past 35 and I still feel like that's the way I should keep going.

• 45:16Speaker 02

  The feeling that you're supposed to know is the thing that can lead you to spend 10 years trying to be something that you're not, right? Trying to be something that actually makes you miserable. The doctor, the lawyer, the whatever, you know, it doesn't have to be one of the traditional careers, but it's some programming or some college course or some parent or professor or whatever told you that this is what good looks like, this is what success means. And you just followed that blindly like it was an A, right? Like it was the A grade. And at some point you wake up and you're like, and God help you if you've like spent $500,000 on medical school, right? And you're like, I don't want to be a doctor. Like, those can be very expensive decisions, both in terms of money and in terms of time. So it's why I'm such an advocate and why I said to my younger cousin,

• 46:00Speaker 02

  like, go figure it out. Like, go be a farmer. Like, really what I learned in my 20s was like, who I am, and what I'm good at, and what I like doing, and what I don't like doing. And as you said, like, I followed that for a while. And, you know, somewhere around, I think like 38 or 39, I hit another wall where I was like, oh shit, this thing that I am like literally the best in the world at, that people, you know, everyone knows me for, that, you know, I'm the COO that runs other people's companies, you have a visionary CEO, go hire Molly, she'll help you bring your vision to life. Turns out I hate doing that now. Like, I was real, I really liked it for a while, and I really don't like it anymore. And that's terrifying. But the beautiful thing is, in theory, I

• 46:41Speaker 02

  have the skills to figure it out, right? Because I built them in my 20s. Doesn't make it not scary. And, you know, I felt lost for the last, a lot of the last, like, three to five years. But it was something I knew I needed to do, right? Because I believe that I should be happy most days of work. And I believe that I should listen to those voices that are like, like, let's, time to try something new.

• 47:06Chris Duffy?

  Well, Molly Graham, thank you so much for being on the show. It's truly been such a pleasure talking with you.

• 47:10Speaker 02

  I know, same. Thank you for having me, Chris. This was so fun. And I'm excited to keep learning from you.

• 47:16Chris Duffy?

  Oh, same, right here, right back at you.

• 47:20Chris Duffy?

  That is it for today's episode of How to Be a Better Human. Thank you so much to Molly Graham. You can listen to her on Ted's Work Life Podcast or read her thoughts at mollyg.substack.com. I am your host, Chris Duffy, and my new nonfiction book, Humor Me, is out now. You can find out more about my live show dates and other projects at chrisduffycomedy.com. How to Be a Better Human is put together by a team that works so well together, they should host their own work advice show. On the TED side, anytime two TED hosts are in a room together, it means a producer got its wings. This week, newly flying are Daniela Bellarezzo, Banban Cheng, Michelle Quint, Chloe Shasha Brooks, Valentina Bohanini, Lainey Lott, Tenshika Sungmanivong, Antonio Le, and Joseph DeBryan. This video was put together by the angelic Ryan Lash, and this episode was fact-checked by Mateus Salas, whose work

• 48:04Chris Duffy?

  and life are both highly accurate. On the PRX side, they sound professional and they look business casual: Morgan Flannery, Norgil, Patrick Grant, and Jocelyn Gonzalez. Thanks to you for listening. Please send this episode to anyone who helps you think through your career and your work life. We will be back next week with even more How to Be a Better Human. Until then, take care.

• 48:32Chris Duffy?

  This episode is sponsored by the Natural Resources Defense Council. Here's a question this show asks a lot: What can one person actually do? Take protecting the environment. When the task feels so big, it's hard to know where to even begin. Turns out, the answer isn't doing it alone. It's teaming up with people who care as much as you do. With the help of 3 million supporters, the Natural Resources Defense Council is in court to defend ancient forests, pristine coasts, and the wildlife that depend on them. None of these places or species can be replaced. They're still here because people fought for them, in and out of court, and that fight needs your support today. Donate at nrdc.org/human, and your gift will be matched five times.

• 49:18Chris Duffy?

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• 50:03Speaker 01

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