Feeling stuck? Why your first job might have all the answers.

0:00Hey everyone, Molly here. When I agreed to come on as the new host of Work Life, I was terrified. But I was also excited to learn from our amazing guests and to share insights that could help all of you, our listeners. One of my favorite takeaways so far came from Kaya Henderson, an iconic leader who told me that leadership is really all about listening and co-creating success with your community. So I have a request for you. Please fill out the Work Life audience survey. It's quick, it's easy, and it's linked in the description for this week's episode. And it'll help us all make this show the best it can be.

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3:49I think it's fascinating to hear accomplished people talk about some of their early work experiences, what shaped them and what they learned. Sometimes I think we overthink first jobs and early jobs. They have to be perfect in our minds. They have to set us up perfectly for the rest of our lives. And that can lead us to undervalue those jobs if they were in a random industry or if you feel like you made a mistake. But the truth is that every single job has something to teach you, particularly when you're just starting out. First jobs are usually full of those learning opportunities. As an example today, I'm going to share a story with you about an accomplished leader's first job and what she learned from it.

4:34And then I'm going to talk about it with my colleague and favorite friend, Ashley Murphy, who you might remember from our FAQ episode. So a different kind of episode today. Welcome to Storytime on Work Life. I'm your host, Molly Graham. Hey, Ashley. Welcome back to Work Life. Thanks for coming back. Thank you very much for having me back. So I want you to listen to this story from Claire Hughes Johnson about her first formative job experience. I loved listening to this story when Claire told it to me, and it left me with a lot of thoughts. So I'm excited to hash through all of the takeaways with you.

5:11As a reminder to everybody listening, Claire Hughes Johnson spent over 10 years at Google in operations and product management and then became the COO of Stripe. She's on a bunch of corporate boards, and she also wrote a book called Scaling People that is one of the Bibles of management and company building in the tech industry. So long story short, Claire has had a really successful career. But this is the story of where it all started at a restaurant in Maine. It was a classic sort of seafood tourist, not a trap, but, you know, sea shanty looking and right on a main drag driving into Camden and attracted all manner of people wanting their seafood on the main coast.

6:00and I come in there gosh I was 16 turning 17 that summer and you can't handle alcohol in Maine or at least you couldn't then until you're like 18 so I couldn't be a waitress I had this idea I'm going to make all this money and be a waitress and save money for college tips right so they're like no but we need a bus girl to turn the tables faster um during the evening sort of and so I would show up at like 4 p.m. and leave at 11 or 11 30 p.m. and there's like it was 172 top restaurant and I was the only one bussing the tables and you think though so here's a lesson that the restaurant manager and in this case it was two women actually who owned the restaurant um that they were the boss but i quickly learned that the bosses of me were the waitresses and the way i actually made money was they had to give me a share of their tips oh and there were five waitresses most of them four out of the five were pretty salty long tenured mainers like full mainer so the one was sort of like nicer to me from the get-go and she was like honey you got to turn the tables faster if you want anybody's tips one of them was named peanut and that sounds cute but she was like about i think probably 68 years old and salty and really but i think i won her over molly it took me all summer but peanut at the end i felt like you know gave me a word of praise like one word of praise but I really I got strong I got strong lifting big trays of stuff I burned off the tips of my fingers helping you know get hot glasses out of the dishwasher to get them on the tables but you kind of figure out the system that you're in and who's actually in charge of your recognition and reward yeah it is not necessarily the people who hired you and it is the people you work with sometimes.

8:13And so that was a big lesson was who's the real boss and who do I need to please? Okay. So one lesson was don't cross peanut, but the second lesson. The real lesson is to be aware of the dynamics in the system in which you're working. Because there was like the cooks and they had a whole thing about how I was allowed to be in and out of the kitchen and when and not. And there's all these implicit rules, right? Totally. Who's going to tell you? How are you going to figure out the implicit rules? And you got to ask for feedback or you got to observe and you got to know where your bread's getting buttered.

8:49Yeah. I always say there's the org chart and then there's how things actually work. Yeah. And if I hadn't figured it out pretty darn fast, I think I would have been out on the curb. Because the first night they were like, too slow. Too slow. You're not going to make it. Pull it together. Pull it together, Claire. This is our livelihood, lady. Get the tables turned. You can see why I like that story so much, huh, Ashley? I can picture Peanut so clearly in my mind. I wish I could meet her. I know. I also have this picture of young Claire Hughes Johnson just running like crazy around this restaurant in Maine and burning her hands.

9:25Trying to figure it all out. I'm so intense, honestly. Totally. I mean, service jobs, whole topic of discussion. But what I was hearing in that story are sort of like three big things that I want to dissect with you today. The first is the value and the power of first jobs. And if you're a listener that's in college thinking about their first job, or if you have kids that are thinking about their first job, what should you think about as you're looking for a first job out of college? The second is in every organization, like I said on the tape, there's an org chart and then there's how things actually work.

10:08So I want to talk with you because I know both you and I have had experience with this about what that means and also how to suss it out, you know? And then the third is how to be new, you know? And what do you need to do to give yourself the highest possible chance of success as you're trying to figure out how things actually work? I'm curious though, what stood out to you about that conversation. Yeah. I mean, for me, so much of what Claire says really resonates, honestly. But I think where I'd love to start is just thinking about the org chart and how there's the one that's written on paper, then also the kind of hidden org chart.

10:43I'd love to kind of dig into how that's been for you in your career so far. Yeah, totally. I mean, I think Claire's story is such a good example of the fact that org and power dynamics literally exist in every single job in the world and that it's not always intuitive. Honestly, I think the first time I really realized this lesson was actually about titles. I came into Google and I just sort of assumed that the most senior people were both going to be the most effective and they were going to be the people that sort of decided everything and directed everything. And I have this very visceral memory of realizing, oh, like number one, just because these people have a senior title doesn't actually mean that they're wildly more effective than everybody else.

11:35And in some cases, maybe less effective, you know? And also that that wasn't how work got done. Like I remember the EA to the person that ran the department was like so powerful. And it took me a little while to figure that out. But then I was like, man, Rowena really runs this whole place. And I feel like that just kept happening again and again. And so I do feel like there were so many lessons for me in that. But one of them was when you show up, you really got to figure out who's actually in charge and how power works inside of an organization. And it really genuinely often does not map to an org chart.

12:19Do we have Ashley experiences about that? I mean, I think so. But I think one part that just stands out to me too, from what you just said, is just how important it is to be kind to everyone. Like that is a best practice regardless, be a good human, right? But also if you're trying to just optimize for, I only have to be kind and thoughtful and polite to this group of people, one, that's not nice, not cool. But two, you might really be hurting your career. You might be really wildly underestimating the power dynamics and where things actually get decided, who actually is going to be in the room and advocate for you when you're not there to speak for yourself.

13:00Yeah. And also how things might change. Do you know what I mean? I think it's such a test of shittiness when you over-optimized for the power structure as it exists today and you were shitty to people and then it bites you in the ass, you know? And like, I always say, you never know who someone might become. So don't let power guide your actions, which again, sounds simple, but is like really important. Right. It's the right thing to do. It also just a really practical, helpful thing to do. And I think in a lot of ways and, you know, so much of this is really unknown and tricky to figure out, but I'm curious, you know, especially for folks that are saying, yes, this is unknown, but help me out here.

13:42What have you found helpful in figuring out how things actually work, what the real org chart looks like at a job? Oh, it's such a good question. Okay. So number one, there are a couple of rules that I have. One of them comes from that experience at Google, which is like the EAs, the executive assistants, or anyone that's supporting a powerful person, like definitely run the company and you need to be their best friends. But to be honest, like if I'm starting a new job, a lot of, and even in the interview process, like a lot of times I'm just asking questions from like, who's on the executive team to like, how do things, how do things work around here?

14:24If I'm, you know, coming in, I'm often working for the CEO. So I like to understand like, who's super close to the CEO, who's super effective at working with that person. A, like, what can I learn from them about, you know, needing to work with my new boss, but also like who isn't as close to them, who isn't working, you know, sort of like as effective or influential in the organization. What can I learn from that? Right. I feel like, yeah, for me, it's sort of that question asking that starts to get me like a sense of who might be, you know, sort of like where on the power hierarchy, you know, and I think part of it just comes with like showing up, assuming that the org chart tells you sort of like maybe how senior people are, how much experience they've had, but it doesn't tell you how power works.

15:16And if you show up assuming that you have to figure out how power works, then it's a combination of like asking questions and then just watching, watching how decisions get made, watching what happens in meetings, watching what works, watching what doesn't work. And through that like study, you eventually kind of like make a map in your head. I guess the last thing I'll just say, which is related to our earlier conversation, is like you also just have to assume the map might change. You know, that what you're mapping is like what's true today. But you might not be able to see what's going to be true tomorrow.

15:48Eventually, once you've been around a while, you can kind of predict how things are going to change. But if you believe, if you sort of like develop a skill in this. But I feel like that map of like how power actually flows or how influence actually flows is one that I always spend a lot of time creating, at least in my head, you know, at the beginning of a job. What about you? I feel like that was a bunch of Molly ideas. How does Ashley figure out how this stuff works when you show up? I mean, well, I love these ideas. And honestly, on the what about question asking, I was thinking, oh, my gosh, that's the kind of thing that makes me so nervous naturally to ask those kinds of questions.

16:24But I love to be asked those kinds of questions, right? Like, it's so cool to feel like you're the college senior who's done it all and seen it all and can guide others. And I think it's a good thing to keep in mind that it may feel scary to ask those questions, but people would actually love to be asked, you know, for the insider knowledge about how things work and how things are done. It's a mindset I want to try to bring forward. I think for me, my main approach is kind of what you described around just being around. My first job was working at a daycare right after high school, which was a crazy and fun experience.

16:58And I just happened to stay late after work one day, just helping to clean up a little bit extra. And because of that, the owner's husband came in. And it turned out that he was actually really involved in the daycare operation, so I was never there during the day. And so by just happening to be there a little bit later and, you know, just mopping or sweeping or doing whatever I was doing and having a chance to chat, It actually really changed how I was assigned in the daycare. I got to spend more time in the newborn room, which was very, very cute, as you would imagine, which was a total goal for me.

17:30And it just actually made a huge difference. Yeah, totally. I also think if you don't work in an office, which, you know, the world is split up now in terms of people that are remote and people that are in an office, how do you like, quote unquote, be around? I know like, I mean, to me, it sounds a little bit like the same concept as like make friends at work, which I know both you and I feel very strongly about. Like it's so easy to be like a work robot and just try to ship things and kind of like be effective at producing work. But one of the most important and powerful things you can do is make friends at work.

18:02Because I always say you take two things from jobs. You take learning and you take relationships. But I think the other really important and effective piece of having like a real relationship with someone is that stories come out about things that they've done at work or the way things have worked or not worked. And through those stories, you can start to interpret the power hierarchy. So building real relationships with people, I do think, is a way to be around. And you can do that virtually. It just requires having a virtual coffee or a virtual lunch with someone instead of just work meetings.

18:38Totally. And I think people get caught up sometimes in this idea of workplace politics being so exhausting and not wanting to engage in this sort of thing. But I think a lot of kind of what I'm reflecting on in this conversation is that sometimes what's called politics or, you know, called the power dynamic can really be addressed by this idea of curiosity. And I think that actually really, it's kind of a theme across this too, right? Like you have your org chart, but get curious about, is this actually the real org chart or not? you have a perception of someone and how they show up at work, but get curious about the why behind why they're showing up that way.

19:14I think curiosity is the kind of thing that can really transform your experience at work and your performance at work, how you're received at work, so many things. Totally. Couldn't agree more. I know. I wonder what, I wonder, I wonder what Peanut's backstory was. I know. I want all the Peanut lore. I literally left that conversation with Claire and was like, peanut is my idol, but also who's, let's like, what's peanut's deal? Yeah. What's she doing now? I am curious, genuinely.

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22:41So another part of Claire's story that really stood out to me is just how hard it is to be new at something. You know, unless you're coming in as the co-founder on your first day, you've already just missed so much. There's already so much shared history and company context you have no idea about. And for Claire, it's just so clear that she wants to do a great job. She has so much, you know, ambition and energy to get started. But there's just a huge mountain to climb at the beginning of being new at anything. Totally. There is so much to talk about with being new and how you set yourself up well to have the highest possible chance of success.

23:19But I also feel like the first thing to just say is that being new is really hard. And it's full of its own kind of pressure. And you can hear it in Claire's story. And you can also imagine her running around that restaurant on her first day not knowing what to do. And then being given the feedback at the end that's like, you got to do this faster. which is always a bummer, you know, on your first day. You're like, oh, I didn't win, you know. Right. Yeah. Let's talk about being new though. Yeah. I'm thinking about, you know, for you, when you think about the last time that you started a new job, what was your number one focus?

23:57What do you try to really get right or prioritize when you are brand new at a job? So it's funny. I just went for a walk with a friend the other day and he's starting a new job for the first time in 10 years. And he was like, I don't know how to be new. And so I sort of said this to him, which is number one, don't try to be smart. I think in your first month, sometimes two weeks, but month, your job is to listen. Your job is to ask every dumb question you can possibly think of and really just to listen and learn. We talked about it when we You're talking about the power hierarchy. That's such a great time to ask a lot of questions and listen and watch.

24:42But you never get to be new again. So there's kind of a moment when everyone's going to start judging you for asking dumb questions. So your first month is not that, right? Your first month, everyone's like, oh, great. You're learning. You're being curious to your point earlier. That's great. And so use that time. Don't try to be smart. Don't try to immediately show value. Just try to learn. That's my number one thing when you're starting a job. Can I add a second? Yeah, please. Because I said this to him too. My biggest thing when I'm hiring new people or when I'm new is like, number one, listen.

25:21Number two, find something that you can knock out of the park in the first 60 days that is going to make everybody say, oh my God, thank God you're here. And so it's like part of what you're doing when you're listening in that first couple weeks or that first month is sort of trying to find that project. And you can ask your manager, obviously. I think a lot of that is their job. But sometimes if they're not as helpful or whatever, or if you're working for the CEO, they're like, I don't know. You got to find it and you got to be like, okay, what's something I can knock out of the park that people will be like, oh, thank God that person's here.

25:58Totally. And I've heard you talk about this idea of just really trying to pay attention to kind of where the pain is in an organization. Because I think that there is a lot of new person energy that you have, right? You have a lot of new person energy to come in and solve things and fix things and make things more efficient. But if you're trying to choose, I think really centering on where are people actually feeling pain right now, where they will feel relief when they hear my name, where they'll think, oh, wow, Ashley's the person that came in and actually really solved the problem that was really slowing me down or making things difficult.

26:32I think it's such a powerful thing to establish early in the game, as opposed to who is this again, or what do they want to talk about? They're like, oh, that person who really helped me. I'd love to check in with them. I'd love to partner with them on this next opportunity. Totally. Is there anything else you think you really focus on when being new? I think for me, it really is kind of tied to the last topic a little bit, but trying to just make a friend. I've been in a lot of kind of strategy and biz ops roles before, where I know for better or worse, pretty soon, I'm going to have some kind of grim rapery kind of things to come and do.

27:07What do you mean by that? Oh my gosh. When I was working at Disney, I was on the strategy team and we had to have some really tricky conversations about, hey, this product line is not performing well. We're actually going to slow it down or we're going to not continue on it at all. Or we have a difficult thing to do around the org chart. we're going to have a reduction in force, you know, these really difficult times. And you really don't want your first chat with someone to be difficult feedback or difficult news. And that's also a big part of the job. And so for me, I really want to make sure that I've had a chat with everyone in some capacity that's not work-related as quickly as possible.

27:48So because I want to get to know them and I'm curious and it's nice to be able to meet these people, but also because when I do have to have that difficult conversation, that's not their first impression of me. We've had to have some rapport and kind of move forward together, I think. Yeah. Like you have to lay a foundation in the beginning of relationships. And it is like the opportunity of the first time you meet someone is to get to know them as a human, right? Not just like as a work robot, as we say. Because you're not trying to execute, you're not trying to like do a project with them. You're just trying to be like, who are you?

28:22And, you know, how long have you been here? How many siblings do you have? Where did you grow up? Like all of those are things you can ask in the first meeting. And then if you get to the fifth meeting and you don't know them, like it just seems sort of weird. So I think that's right on, like get to know people as people. And I like your compass of like make a friend. No, and I think the point about, you know, this, the window being small, it's such an important one, you know, to what you're saying about the window to ask all the questions, the window to chat with someone before there's any real expectation of delivering on something.

28:52That is a small window. And I think being new can be this scary, intimidating time. But I guess a reframe of it is also this very special moment when you have a lot of space that will eventually go away to really explore and expand and just, you know, let your curiosity go as well as it wants to go before things really shift for you and expectations really change for you. Yeah, totally. No, you're making me think about how emotional it is to be new. I was just talking to someone last night. Man, I've been having a lot of conversations with new people lately, so this is all very relevant. You've been walking and talking and just talking, meeting all these new people.

29:33Yeah. So she was talking about, she is eight months into a new job and she was talking about all the emotions of being new and what a roller rollercoaster. It was. And I think a lot of what she talked about, which I really resonate with, is just feeling really insecure, like feeling like she had to prove herself again and feeling like people, you know, being worried about being judged and all of that. And I think being new really does come with such a rollercoaster. And it's often quite a bit longer than you wish it was. You know, I got an email a month ago from someone who started a new job that was literally like, how long does this last?

30:18Like how long until I know whether these emotions mean it was a mistake or not? And I wrote her back and it's actually very much validated by this woman that I talked to last night. And I said like six to nine months, like you need six to nine months to start to feel like yourself in a new job. And that means you do need to expect a real roller coaster for a while. And this woman that I talked to last night was like, yeah, right around six months, I started feeling confident and more secure. So I really do think that time horizon is very real, which is you're going to feel new, insecure, imposter syndrome, all these things for a while when you start.

31:00That's so important to normalize. I think people in general are so likely or so prone to setting these artificial deadlines for themselves for when they should feel better about things. You read the first 90 days and you say, oh, I guess it's 90 days and that's the window, you know, or you see someone else that seems to be adjusting faster and you say, oh, that must be the appropriate amount of time to dive in. Yeah, or something's wrong with me. You know what I mean? Like they look comfortable. Why am I not there yet? Right, right, right. And so I think it's so powerful to really expand that window and give yourself some grace about how long it might actually take and how taking that long might mean that you're doing the best possible job, you know, that you're doing it exactly the right way and you are pushing yourself and growing.

31:45And this is just the moment that it takes to transition. What else from Claire's story made you think, like, what else did you think about being new, going back to all these experiences we've had, being new in jobs? Yeah. Well, I'm thinking about the other side of it as well. You know, it's tricky to be new, but oftentimes we're the ones that are hiring someone else. You know, what do you try to do to make it easier for someone else to be new, given that you know the experience and kind of the emotions of joining. Yeah. It's funny. I actually feel like somebody could have done a better job setting Claire up for that job.

32:20I'm guessing nobody thought about it because they all just knew how things worked, but nobody sat her down and said, hey, you're going to have to bust 172 tables. Here are the things that are important. And by the way, your reward system is that your tips come from the waitresses. So make best friends with them. And I do think that like when I'm onboarding someone, a lot of – that's like a lot of what I try to do is just as much as possible give them a map. Like we talked about like when you show up trying to draw the map for yourself and I feel like one of the best things you can do as a manager or a leader is like give them a sketch, you know, to start from.

32:57But the other thing I really try to do is find that project that the person can knock out of the park. What is the thing that if they come in and they do a great job at it, it will make everyone around them think, oh, thank God they're here. But it's also a proving moment for me of is this person who I thought they were when I hired them? And I think helping them identify that project and also understand what good looks like is such an important thing for setting people up for success. What about you? What jumps to mind for you? I think when you're talking about setting someone else up and how maybe Claire wasn't set up first, success in the first place, it makes me think about how at some workplaces it's kind of a badge of honor to learn things the hard way.

33:44And I think we have the opportunity to actually not perpetuate that culture. I can imagine, and again, I don't know Peanut, wish I did, But I can imagine that, you know, other folks that were in Claire's role didn't get a great onboarding and worked their way up. And they kind of saw that that was part of the process. So, you know, we don't need to walk anyone else through. You figure it out the hard way. It makes you tougher. It makes you stronger. And that's just part of the process. And I've definitely been at places like that. You know, my first job was working on Wall Street, which I think has a little bit of that culture of kind of just trial by fire.

34:15and there's such a cool opportunity to actually say, yes, people here often do learn the hard way, but once I'm a manager, once I have a little bit of ability to be a leader and to set the onboarding approach, how can I shift it and make it a little bit different and friendlier and make it a nicer on-ramp, you know? Yeah, totally. How can I make it so that people don't get on the wrong side of peanut? Right, exactly, exactly.

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36:17Get ahead of the curve with an LA28 hospitality package. Discover more at hospitality.la28.org slash worklife. This episode is brought to you by Founders Mentality, a podcast in partnership with Bain & 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 Lara 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.

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37:35So the last thing that I really felt listening to Claire's story is just this kind of overall sense of nostalgia for the first job. You know, and your life is such a powerful milestone to actually be earning money for the first time and kind of part of the world in this new way. And it led me to kind of reflect on what I want to tell someone who's looking for their first job themselves or also maybe helping, you know, their own child or their mentee find their first job. And, you know, I'm curious. I know a bit about this, but I would love to make sure that everyone knows a little bit about your first job because it's so different than what I would normally do.

38:10And it's so interesting. Can you just share a little bit about what your first job was? Yeah, totally. So when I think about my first formative job, it genuinely was my first job out of college. I had a lot of friends that were going into an investment banking, and that is not what I did. I ended up becoming a wilderness instructor for a school called Knowles. And I had done a student course with them in college where I went to Alaska for three months and did like mountaineering and sea kayaking. And then they asked if I was interested in becoming an instructor. And I was like, huh, never, I didn't really think of myself as outdoorsy before all of this.

38:51So I ended up taking their instructor course and becoming an instructor and spent the first year after college leading wilderness trips in Patagonia and in Alaska. And these were like 75 day wilderness trips like sea kayaking and mountaineering leading groups of about 16 students and I will tell you when I told my parents what I was gonna do I feel like their reaction was like what what is that a job like what is that you know and they were nervous I think about both like where it was gonna send me but also like I don't know probably also for my safety um because they're good parents. Knowles ended up being one of the most valuable things I've ever done because I um it taught me how to be a great manager like I think just being in sort of somewhat high pressure situations where like actually people could die like Knowles is very safe so like we never encountered real danger exactly although now that I say that I'm like yesterday I told someone a story about a pod of orca whales swimming right next to our kayak.

40:02So that's dangerous. That does seem dangerous. Yeah. So there's like real consequences, you know what I mean? Which is not always true in the corporate environment. Totally. And I feel like learning to lead where there is more sort of visceral consequences was really powerful. And there's lessons I still talk about today, frameworks, models, just things I experienced on those trips that I still use today. And yeah, it was like I couldn't have designed a better first job even if I really stumbled sideways into it. I have a lot of thoughts about this, especially the orca whales, but I will save that for after recording.

40:43But I think I'm also curious about like the friend reaction because I think sometimes for me, you know, you have a group of peers and especially a moment like college, you're just all together, right? You're all freshmen, sophomores, juniors, seniors. And then all of a sudden, the paths diverge. And so when you have these friends that are doing things that are really good on paper, you know, maybe it's your consulting friends or your Wall Street friends or the jobs that are kind of approved universally with a stamp from society, how do you think about that moment? You know, how did that feel for you to have friends doing more traditional things, but kind of knowing that you wanted to take a different path at that exact moment?

41:23Yeah, I, a lot of my friends did go do, either they kind of knew what their path was, which I definitely didn't. You know, I didn't know what I wanted to be when I grew up. Still don't. But I, I feel like a lot of my friends were going to do more traditional stuff or going to back to graduate school, going to law school, going to different kinds of school and, or going to Wall Street, because that was like a big thing when I graduated. Tech was not really a thing when I graduated. I think probably similar to my parents. They were all like, that's pretty weird what you're going to go to. But I think a lot of them thought it was cool.

41:59Like they were like, oh, that sounds fun. You know, that doesn't sound like it should be a job. It sounds like it should be something you get to do for free. And yeah, but I felt like an odd duck a little bit, you know, like everybody was swimming happily in one direction. and I was kind of like, I don't know, swimming off like down a steep rapid or something like that. Totally, totally. Do you think that that feeling itself in addition to the actual content of the job was helpful for you to experience early on? Like for me, I went from this Wall Street job that was very good on paper to working at a nonprofit right after and got some of the big reactions of like, wait, what are you doing now?

42:41Well, how will you live in New York? Like, well, what does that make any sense? Like, is that what you went to college for? And the nonprofit itself taught me a lot, but also this experience of actually making a switch that wasn't automatically applauded by everyone was so valuable for me to experience early on to know that I could make a choice that I didn't need everyone's approval. That's such a powerful thing. And I think actually a lot of people can get a really long way without ever testing that out. If you get A's in school and you go to a good college, then you get a good job, you get promoted there, you can go a long time always making choices that are also approved.

43:23And so the first time that you actually try to go to the other path or peek over to the left, it can be terrifying, I think, for so many people. Totally. And I think there can be a lot of pressure. You know what I mean? I think I was just emailing with my cousin who's a senior this year in college asking her a little bit about kind of like how people around her are feeling because I think it's a hard time to graduate because there's a lot of at least talk about it being very, very hard to find a job as a new college grad. Right. And whether that talk is true or not, it changes how you feel. But she was saying, you know, everybody feels a lot of pressure to find the right job, not just any job.

44:04Right. And that really brought me back, you know, because I think that that's like one of the things I hope people take away from Claire's story is like there's no such thing as a right job. Do you know what I mean? Like any job that sounds fun to you, that earns you money, that turns you into an independent adult, that starts you on a path of learning how to work and how to be effective in a workplace is a good job. because you're going to learn as long as you bring your curiosity glasses to your point. You're going to learn so much from just having to exist in a workplace. I learned so much from Knowles and it is not what I'm doing today.

44:44Claire learned so much from Peanut and it is not what she's doing today. Ashley learned so much from the daycare and it is not what she's doing today. So I really think understanding that it's fine. Any job will be a great job. Any experience can teach you something if you let it. So releasing some of that pressure is important. And sometimes people will look at you sideways, whether it's your parent or your peers. And that doesn't mean anything about where it'll take you. Right. Right. And it's interesting, too, what you're describing, because in some ways I hear a little bit of this idea of maybe release the pressure on the job itself or the experience itself, but potentially increase or at least make sure there's a good amount of pressure on how you show up there.

45:32because, you know, Claire could have gone to this job and finished out her summer and not learned anything, right? But she actually was able to show up in a way that allowed her to take lessons that were applicable to her even as COO, right? And so I think there's a way to show up at a daycare or at Knoll's or on Wall Street and have a transformational experience. And there's a way to get a paycheck and go home. And so it's kind of like, what mindset are you going to bring to your first job in any job, even beyond just what job are you going to pick or, you know, be kind of pushed into in some way.

46:09Yeah, totally. No. And I think some of that comes from just wanting to be good at it. You know, like I think what was interesting about Claire's story is like she could have after that first day, you know, when she got feedback of them saying like, you need to move faster, like been pissed or like quit or like been frustrated. But instead she was like, no, I'm going to try to be a great bus girl, you know? And I think there is a lot of power, again, in literally any context, any job of just trying to be good at that job and accepting that you'll learn something from trying to be a great bus girl, even if it's not your long-term destiny.

46:43Even if you're not like, I want to be a bus girl in 30 years, you can still learn a lot from that. And so I agree with you completely. It's release the pressure on it being the perfect job or the perfect path or setting you up for the perfect next thing, but put pressure on yourself to like learn how to be good at whatever it is you're doing, to like want to leave with people saying, oh, we're going to miss that person or she was really great at that or they were important to us. Like you want to leave a reputation behind you that people would want to work with you again. You know, that serves you really well no matter what.

47:16But the lessons are also come from sort of like trying to be good in a place, all these different contexts, you know? Right. Absolutely. Yeah. I think it's both, it's both the pressure release and maybe a pressure cooker. And in some ways, I don't know if listeners are going to feel relieved or more stressed out by this, but I think there is real power in this idea that you don't have to get the experience just right. Sometimes experiences are really outside of our control. You know, you don't get the job that you dreamed about having, or you get laid off, or all sorts of things happen, but you do actually have a lot of control over how you show up in an experience.

47:52And that might be the place where regardless, the most learning comes from anyway. So there's something both comforting and a little terrifying there maybe. Yeah, totally. No, and I think you just can't predict where things are going to go. So like all you can do is control how you show up, you know, and control how people think of you, right? The impression you leave behind. I am curious, Ashley, like it does seem so stressful to graduate from college today. Like, I mean, maybe it's the same as when you and I graduated, but like, what would you say to people graduating from college right now looking for a job?

48:27This is going to be, I think, a nerdy answer. So prepare yourself. My favorite kind? I mean, I think for me right now, if I were graduating right now, I think my big favorite would be AI, right? It's so unknown still. There are so many articles every day about how it's replacing all the jobs and the jobs that were good jobs are not good jobs anymore. And it's kind of this idea that at this moment, technology is the thing that's going to make it impossible to find something right. But I was reading about how when writing was first coming about, you know, literally writing, Socrates thought it was going to be this awful technology that was going to take all of the good things away.

49:10It would take away our ability to think. It would take our ability to really transmit wisdom effectively. It was this tech change that was going to really destroy what the world could and should be. But I think most of us feel now that writing is actually a very useful thing for the world. And there are lots of opportunities that have come about because of writing. And we've had the opportunity to think about how writing actually helps you to think even more effectively. And so these moments that feel like they are game-changing in a negative way are not new. And sometimes they have these effects that are really powerful and positive that we can't see right away.

49:47And that's what I would want to really center out when it comes to AI. There are themes around AI that are similar to themes around offshoring jobs a few years ago, or other technology changes, or even back to writing itself. So we don't have to feel like we are just completely out in an ocean for the first time. People have been here before. Civilization kind of flows through these moments. Yeah, I totally agree with that. And I also think what I hope for people is to approach things with curiosity and creativity versus fear. And I know it can be hard because there's so many news stories all the time.

50:20But I feel like that's just a good way to leave the nest of whatever educational experience anyway, which is just go Go try things. You don't know what you're going to be good at. You actually don't know what a good job is going to look like for you, let alone a good job in the world of AI. So just go try things. And I think that's like, for me, I know some people show up in their 20s thinking they know what they want to do. They want to be a doctor or I have to tell the story of my college best friend who knew she wanted to be a paper conservationist, like the kind of people that restore old, not even works of art.

50:59Like some of them are works of art, but a lot of it is just old paper, old documents. And by the way, that is what she does today. She is the head of paper conservation at Harvard Library. A lot of paper over there. But so she came into college being like, this is what I want to do. I came into college being like, no idea what I want to do. And both are fine. Like I feel like there is a lot of pressure to know in your 20s who you want to be and what you want to do. And I would just really release that because I've also seen friends who thought they wanted to be doctors go all the way through medical school, all the way through residency, and then be like, whoops, I didn't want to do that.

51:37So it is better in a lot of ways to adventure early, to like try and experiment and learn about yourself, including things that you hate doing. You know, you may never want to be a bus girl again, but at least you know that, right? There's so many jobs I've had where I'm like, whoops, never – I shouldn't do that again. Nobody should hire me to do that again. But at least I know that because that's part of learning what it is that you do want to do. Right, right, right.

52:32It just has to be a sort of adventure of discovery for yourself about who you are and what you're best suited to do in this world. That's a much more optimistic framing of I've got to get out there and get it right. It's like I get to have an adventure. And, of course, there's real constraints to keep in mind for everyone, everyone that looks different. But you have space, maybe more just than you might realize, to experiment, to try, to really go on a big adventure. And it's kind of an exciting moment if you can frame it that way. Yeah, if you can think about it that way. Okay, Ash, to end, let's each pick one thing that the other person said that we want to take with us from here.

53:14I want to say that I loved what you just said about history. I think about that a lot, that we often feel like the moment in time we're in is so unique and people say the world's coming to an end, so it must be actually about to end. And actually, history is often a story that looks very similar at different moments in time, particularly when big new technologies get introduced. My dad always says that new technologies always do as much good as bad. That means that they're never inherently good and they're never inherently bad. You think about the car, like the automobile, we wouldn't get rid of it.

53:55It's been massively valuable to the entire world. And it's been a significant contributor to climate change. So a lot of these things, AI included, I think, do a lot of good and I think will produce a lot of good and will do a lot of bad. But it's not all bad. It's not all like jobs being eliminated. I bet there will be lots of jobs created as well. And that to me is something that I think is just good perspective to keep when you're thinking about this. That makes sense. Fifth century BC has got lessons for us all. I think for me, what I want to really remember is just this piece around giving yourself grace about not only the emotions of being new, but also the time in which you can really feel like you're on that emotional roller coaster.

54:40I'm definitely someone that can kind of set a deadline for myself that no one else has set around when I should be feeling a certain way. And I want to really remember this idea that things can take longer than you think to really settle in to get comfortable. It could take six months. It could take nine months. But when you're doing hard things especially, it's important to keep in mind that you need time to really adjust and get settled in and feel comfortable. And that's not an outlier experience. That's really the norm. Well, this is awesome, Ashley. Thank you for listening to that story with me and getting as much out of it as I did.

55:13And well, thank you, Claire, for telling us it because I feel like Peanut has a lot to offer the world. Yes. And thank you, Peanut, wherever you are, rooting for you as well. 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. Banban Chang is our story editor. Mixing by Hansdale Shi.

55:48Ted's executive producer is Daniela Balarezzo. Constanza Gallardo is the executive producer for Pushkin. Special thanks to Roxanne Hylash, Valentina Bohanini, Lainey Lott, Tansika Soongmanivong, and Ashley Murphy. I'm your host, Molly Graham.

56:15When you think of Monica Lewinsky, you might immediately think about the White House scandal from the 90s. But I think of someone who is so surprisingly and genuinely hilarious. This 27-year-old guy hit on me that evening after my talk. And it was amazing because his pickup line was, I can make you feel 22 again. And, you know, he's cute. So maybe I thought about it for a second. But maturity prevailed. And I was telling a friend of mine this story on the phone that night. And I was like, you're not going to believe what happened to me. And I said, I'm probably the only person over 40 who doesn't want to be 22 again.

56:57That was a snippet from my live interview at TED 2026 with Monica Lewinsky about how she's reclaimed her life in the past 20 years, what we can all learn about shame and redemption, and how to laugh even when things are falling apart. You can listen to our full conversation on the How to Be a Better Human podcast. It might just surprise you. Thank you.