Is It Too Late To Start Over? with Ailsa Chang | Crooked Media
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June 28, 2023
Work Appropriate
Is It Too Late To Start Over? with Ailsa Chang

In This Episode

There’s a persistent idea that when you finish high school or college, you pick a career and then do that one thing for the rest of your life. But what if you get a few years, or even decades, in… and you hate it? Can you pivot? Ailsa Chang, host of NPR’s All Things Considered joins host Anne Helen Petersen to answer listeners’ questions about making a change.

Need advice about a sticky situation at work? Head to www.workappropriate.com and tell us about it. Some episodes we’re working on include problems around taking a much-needed vacation, juggling parenthood with work, and making caring professions (e.g. teaching, nursing) more sustainable.

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TRANSCRIPT

 

Anne Helen Petersen: Hi, everyone. I’m Anne Helen Petersen. And this is Work Appropriate. [music plays] Maybe you’re like me and you grew up with this idea that at some point in high school or college, you’d pick what you wanted to do, and then well you’d do it for the rest of your life, I think a lot of people around my age internalized that idea from their parents or their grandparents, who often did figure out what they were going to do, even if it wasn’t something they ever felt like they chose, per se. And then they kept doing that thing for decades. My granddad, one career, my dad, one career. There’s a lot of structural reasons why they were able to do that. And even though the economy has changed so much over the last 50 years, that expectation of one career somehow has not. At least not for a lot of people who’ve told me about the quiet shame they felt having to, quote unquote, start over in a new career. But it’s not starting over. You’re just taking a different turn and taking all your knowledge and experience with you to be applied in different and surprising ways. You’re pivoting, and I know that that sounds like business speak, which is something we would try to avoid on this podcast. But sometimes business speak can do something valuable for our brains. That and hearing from other people who’ve pivoted and realized, yes, it’s hard, but it can also be amazing. Trust me, I know from experience, and so does our co-host, whose voice NPR listeners will definitely recognize. [music plays]

 

Ailsa Chang: My name is Ailsa Chang, and I am one of the hosts of NPR’s All Things Considered. 

 

Anne Helen Petersen: So hosting a beloved national radio show was not always your plan. You were a lawyer into your thirties. [laughter] 

 

Ailsa Chang: I was. I was. 

 

Anne Helen Petersen: So what’s your own story? I also had, like, a real career pivot. So what’s your story of making one? 

 

Ailsa Chang: It’s so funny because I feel now the journalism thing was this just very fortuitous, happy accident. And a lot of people who have career transitions don’t get to say that. But I was always convinced that I was going to be a lawyer. Like, I was one of those people in high school who did like competitive speech and debate. And I have these Taiwanese immigrant parents who are like, well, if you’re not going to be a scientist or a computer programmer or a Wall Street banker, then and you like words, well, I guess then you’re going to be a lawyer. And I kind of happily bought into that plan. I like the idea of holding court, I guess literally like in the [laughter] courtroom and giving these fiery speeches. 

 

Anne Helen Petersen: Totally.

 

Ailsa Chang: To a judge or a jury. And I actually I loved law school. I loved clerking. But it was at the law firm. I was at this large litigation firm in San Francisco. It’s called Munger, Tolles & Olson and I self-selected into this place because the people who worked at Munger who who work at Munger today are some of the most talented lawyers I’ve ever met in my life. I mean, these are like former Supreme Court clerks, former federal prosecutors. These are people who literally, I believe, could do anything they want to in life, but they all chose to be at this law firm. So while it was like a little rough at the beginning, I thought to myself, I just need to stay here longer and I will discover the thing that’s keeping them all here. But it was a bad fit. I joked to people that being a litigator is like the worst combination of being really bored and really stressed at the same time. [laughter] And beyond that, though, like law firm life, it didn’t tap into, like, the pieces of myself I liked best. And I didn’t realize this until later, like, I couldn’t put into words at the time. But, you know, there’s a part of me that loves to be curious and follow my curiosity wherever it takes me. There is a part of me that loves, loves, loves getting to know people from all walks of life, like really get to know them, really sit down and get into life with them. And then I’m just, you know, I can be this crazy, free spirited, whatever, you know, say whatever I want off the top of my head and not carefully think about every sentence that comes out of my mouth. And I felt like being that person didn’t fit into the culture of a large law firm. 

 

Anne Helen Petersen: Yeah. 

 

Ailsa Chang: And so I just felt so unhappy. But I was someone up until then. This is now like my early thirties, where I had just followed like a single track 

 

Anne Helen Petersen: Yep, yep. 

 

Ailsa Chang: My entire life. Like I was that straight-A student. I was like that machine in high school, and I was a machine as a student in college and law school. And when I got spit out into the real world at my first real job, it was mind blowing and scary to me to discover, oh, my God, like, even when you follow all the steps that you have like, set out to achieve, you don’t necessarily check off the most important box. And that is happiness. 

 

Anne Helen Petersen: Totally. 

 

Ailsa Chang: And so I’m at this law firm and I think I don’t want this life. So I just ran away. I basically, like, gave I think it was one week’s notice. 

 

Anne Helen Petersen: Wow. 

 

Ailsa Chang: I had absolutely no plan. No plan. And that was the first time in my life I never had a plan. And to do something so drastic, quit a huge job without a plan was so uncharacteristic of me, but I didn’t know where I was running towards. I knew I wanted to run away from law, but not running towards anything in particular. So I took a few months off. I’m living in San Francisco at this point, and not only did I not have a job like a place to go every day, I had just gotten dumped by my boyfriend. I had just gotten foot surgery, was walking around in this like stiff walking cast.

 

Anne Helen Petersen: Yeah. 

 

Ailsa Chang: I was like limping around. My parents were also extremely pissed at me, like, devastated with my choice. 

 

Anne Helen Petersen: Yeah, yeah. 

 

Ailsa Chang: Because they were so proud that I was a lawyer. And it was the first time in my life that I was grappling with my parents. Being ashamed of me really disappointed in me. So I had all of this swirling around and I was just kind of hanging out in my apartment and I knew that wasn’t a healthy place to be day in and day out. So I signed up for an internship at KQED, the NPR member station in San Francisco. 

 

Anne Helen Petersen: Wow. 

 

Ailsa Chang: Because I was like, you know what? I can’t just stay inside all the time. And I was sort of a public radio listener, like, I wasn’t a devoted public radio listener, but I would listen to these people on air locally in San Francisco and think, oh, they seem smart and down to earth and engaged with the world. Maybe if I just like, hung out at a place with people like that, I can figure out my life. Like slowly but surely I arrive at KQED. I remember, like, the interview first of all for the internship. They were like, are you sure you want this internship? Like, first of all, it’s unpaid. You are like way overqualified. And I would be interning with 20 year old’s, 19 year old’s, people who are still in college, answering the phones, taking notes. And I was like, yes, this is what I want to do. The other interns got such a kick that I was there. [laughter] They were like, what are you even doing here? Answering the phones with us? But I ended up having such a blast at that internship. 

 

Anne Helen Petersen: Yeah. 

 

Ailsa Chang: I just I felt such freedom to jump from topic to topic, like, you know, in litigation, you could stay on a case for years and it can be the most boring, excruciatingly boring case in the world. [laughs] 

 

Anne Helen Petersen: Yep. 

 

Ailsa Chang: But if you’re on it, you’re on it. And in journalism, I mean, if a story ceases to be important or interesting or irrelevant, then you got to get out of that story and find another story. Right. And I thought that that was really liberating. I was a booker, meaning, like I pre-interviewed guests for the show. 

 

Anne Helen Petersen: Yeah, yeah. 

 

Ailsa Chang: And I loved just being able to deep dive into one topic, write a bunch of prep on it, prepare the host on it, and then move on to another topic. And what I also loved when I was pre interviewing, but what I began to see the seeds of is that connection you make in an interview and how like if you ask the right questions and you approach with the right tone, the right curiosity, the right openness, you can actually help people become the most interesting versions of themselves. 

 

Anne Helen Petersen: Totally. 

 

Ailsa Chang: There’s there’s a collaboration in it. It doesn’t have to be adversarial. Sometimes it it needs to be it’s a needs to be more confrontational. But sometimes you’re helping someone actualize the best version of themselves they can be. And I loved that. I love that piece of interviewing. And so sorry, this is such a long winded answer. 

 

Ailsa Chang: No I love it. [laughter] 

 

Anne Helen Petersen: That’s that’s how I decided, like I want to do more of this. And they were like, all right, then maybe you should go back to school. And so I did. I went to Columbia Journalism School in my early thirties, and that’s how I eventually started that trajectory into public radio at NPR. 

 

Anne Helen Petersen: So there are a few things that I will note here. One is that I think a lot of people will identify with or recognize parts of their own path, and they’re like, oh, I thought that I just wanted the best of the best, right? And I followed that trajectory, and maybe that was internally motivated. Maybe it was more externally motivated. Maybe it’s a mix of all those things. But then you wake up at some moment and you’re like, did I choose this choice? 

 

Ailsa Chang: Right. 

 

Anne Helen Petersen: Is this actually what I want? 

 

Ailsa Chang: Yeah. 

 

Anne Helen Petersen: And I think that, like I love your phrasing of I realized that the job wasn’t activating the best parts of me because I think sometimes we fall back on to  like I’m not passionate about my work or I don’t love my job. And those are they’re sticky phrases that I think difficult to get our heads around. 

 

Ailsa Chang: Yeah. 

 

Anne Helen Petersen: Instead, if we think about not, no one needs to be in love with their job all the time. 

 

Ailsa Chang: Exactly. 

 

Anne Helen Petersen: Some people are, but a lot of people don’t have to be. But you shouldn’t think that your job doesn’t activate the parts of you that are most valuable, that are most beloved to you. 

 

Ailsa Chang: Yeah. 

 

Anne Helen Petersen: And so the last thing that I’ll note is something that I think a lot of people are either anxious about or can’t envision, which is, do I have to go backwards to start over and not even thinking of it as backwards, right? It’s just like I have to go somewhere else. And there’s if you’ve gotten to the point where you’re in like your early thirties or later in your career, there’s something terrifying about going back to that place that you feel like you’ve already gone through that gauntlet. 

 

Ailsa Chang: And it’s the language that does such a disservice. Like going backwards—

 

Anne Helen Petersen: Totally.

 

Ailsa Chang: —is the wrong way to look at it. You’re going linearly. 

 

Anne Helen Petersen: Yeah. 

 

Ailsa Chang: I mean, gone are the days I meet very few people these days who have just like one career, one company. 

 

Anne Helen Petersen: Totally. 

 

Ailsa Chang: It’s those twists and turns, those pivots and tweaks that you go through along the journey of a whole life. You know, you can have multiple careers and even what do you define as a career is its own malleable thing. You know, like in retrospect, my journey makes sense because, oh, like in law, you learn how to like, question people and you learn how to, you know, poke holes in people’s arguments. That leads into journalism. I mean, but at the time I was bumbling around, I didn’t know what the next step was going to be. But here’s the thing. The heart of it is. You spend so much time working, right? Like most jobs are at least 8 hours a day. 

 

Anne Helen Petersen: Yeah. 

 

Ailsa Chang: They’re often longer than that. That’s a huge percentage of your time. I feel like if you had the choice to choose your work and I know that that in itself is a privilege. Not everybody can choose their work, but if you have a choice, you owe it to yourself not only to be happy, but you owe it to yourself. Not even to be like mildly bored all the time. 

 

Anne Helen Petersen: Yeah. 

 

Ailsa Chang: And I told my mom, well, my parents were so pissed me so angry, so disappointed at me. They were like, why would you throw away your law career? You just spent the last eight years of your life investing in this law career, right? If you count the years in law school, the years you clerked and then went into a law firm that was like about eight years at the time when I quit, I was like, If I love what I do and I hope to find the thing that I love, I hope that I will be working into, I don’t know, my seventies, maybe eighties. 

 

Anne Helen Petersen: Yeah. 

 

Ailsa Chang: Health permitting, that’s like five decades. [laughter] You want me to stick to something because I spent the last eight years doing it for the next five decades? Are you serious? 

 

Anne Helen Petersen: It’s a way of thinking about education and experience as only useful to that particular vocation. Right. 

 

Ailsa Chang: A hundred percent. 

 

Anne Helen Petersen: And I really struggled for a while once I left academia to think of like, oh, did I waste time on that PhD? Right. Especially since I moved into journalism and I saw people who had gone, you know, who didn’t have necessarily any degree and were making it in journalism. And I was mad about the student debt most of all. But I was also mad about like I spent all of this time and I delayed adulthood in all of these significant ways. But now I really think of that PhD as teaching me how I approach the world, right? Texturing my thinking, like teaching me how to think. So. 

 

Ailsa Chang: Yes. 

 

Anne Helen Petersen: I have more gratitude. I’m still mad about the student debt. 

 

Ailsa Chang: [laughs] Yes. 

 

Anne Helen Petersen: But I have more gratitude and more, I think, like distance from it. And I think that’s useful. It’s hard sometimes to do it immediately, but I think it’s really useful to think of it as experience, not as a waste. Okay. Okay. There is so much to talk about here. Like so much. But I want to get into our questions. This first one is about getting off the path you started on right out of college. This is from Audrey. 

 

Audrey: I’m 29 and work as a product manager at Amazon. I happened in the product management when I graduated college. An alum was interviewing for the start up on campus and I grabbed one of those little paper dangles from a bulletin board for a slot. I never actually chose product management. I was just 22 and needed a job and then it was always more convenient to keep doing it than switch roles. Seven years later, it’s turned into a career and I’m left wondering if it’s what I really want to do. The problem is I don’t know what else I would want to do, what jobs are out there. I don’t need work to be my identity, but I don’t want sitting down to work each day to be the struggle that it is now. I don’t have to love it, but what am I liking it? I don’t want to look back and have my career be something that just happened to me. I want to choose it with intention. The only problem is I don’t know what I want. How do people choose? Especially when many careers require significant investment like school? 

 

Ailsa Chang: I love that we’re starting this question because this is maybe the hardest question 

 

Anne Helen Petersen: Yeah. 

 

Ailsa Chang: About career transition, right? 

 

Anne Helen Petersen: Yeah. 

 

Ailsa Chang: Well, a lot of people often start at the point where they know what they don’t want to do. 

 

Anne Helen Petersen: Yeah. 

 

Ailsa Chang: But they don’t know what they do want to do. So how do you pick that? And I can just, you know, speak from my own process. 

 

Anne Helen Petersen: Yeah. 

 

Ailsa Chang: When I knew I was very unhappy at the job. Well, first of all, I that is when I was at about 26, 27, at the time when I was like getting very profoundly unhappy, that’s when I started seeing a therapist for the first time in my life. 

 

Anne Helen Petersen: Mm hmm, yup. 

 

Ailsa Chang: Very regularly and understanding at a very basic level why it was so hard to even contemplate quitting. Then I systematically set up informational interviews with people I admired who did jobs that I wasn’t sure I would like, but I thought, let me just talk to them about it. And I’m kind of conflicted about the whole informational interview thing. Yeah, you get to talk for like, you know, an hour or so, but I feel like you need to experience the work to really know if it will click with you, but you need to start somewhere. So maybe just having a bunch of conversations with people and talking to them about what their jobs are like, why they picked that job, what they hate about their job. Always ask what they hate about their job. 

 

Anne Helen Petersen: Yeah. 

 

Ailsa Chang: But I had to say like I couldn’t really jump into what do I want to do with my life until I quit. And I know a lot of people don’t have that luxury. 

 

Anne Helen Petersen: Yeah. 

 

Ailsa Chang: I had some savings. I just knew that I couldn’t think carefully and intentionally about what the next steps would really be if I was working 12 hour days and often weekends. 

 

Anne Helen Petersen: Yeah. 

 

Ailsa Chang: So I quit and I actually signed up for an online career coach that gave me this structured way to think about what I was good at, what I enjoyed and what I wanted to avoid. So I took like a battery of skills tests and personality tests. [laughs] I answered questions about like what kind of work environment I would thrive in. Did I like working in groups or did I prefer a more solitary environment? Did I like long term projects or daily changing projects? Was I someone who liked to work at a desk indoors, or was I somebody who needed to be in motion all the time? Maybe outside a mix of all of that? And it was really eye opening to go through this very deliberate, self-conscious, intentional process of getting into the guts of. What work I would enjoy. And it made me realize that finding work you enjoy is a multilayered thing. It’s not just like the tasks. It’s also what kind of people do you want to be surrounded by? What kind of literally, like what kind of environment do you want to be in physically and what’s your attention span like? Like, I never thought about work in such a multifaceted way. And the most valuable insight I got from this online career program was that I really, really liked to meet different kinds of people and connect authentically. 

 

Anne Helen Petersen: Mm. 

 

Ailsa Chang: With them. And I needed to find a vocation that allowed that constant personal connection. And then the next thing I also did, which this person may want to consider, is I asked my friend. 

 

Anne Helen Petersen: Yeah. 

 

Ailsa Chang: What they thought my greatest strengths were, and a lot of their answers coalesced on you’re curious about people you want to know people at a deep level. Also, they were like, you’re a really great storyteller. Like, I love as you can see, I’m like, just keep on talking and I can’t stop. [laughter] Like, I love telling stories. 

 

Anne Helen Petersen: Yeah. 

 

Ailsa Chang: And I like to teach people things. But if I may think of your job as an opportunity that can train you, that can require you to be the person you want to be. 

 

Anne Helen Petersen: Yeah. 

 

Ailsa Chang: Like what I love about being a journalist, the reason I think it’s sticking so well with me is it forces me. It requires of me to develop attributes that I want anyway as a person. 

 

Anne Helen Petersen: Yeah. 

 

Ailsa Chang: I want to be someone who’s a good listener. I want to be empathetic. I want to be curious about the world. I want to be open to opposing viewpoints and open to having my mind changed. I want to make people feel comfortable talking to me, to feel unguarded. And so like, what can I do to help them open up? Like these are all the things I want to be in life. And I literally have a job that helps me practice doing all of these things. And so I feel this continuity between the person I want to be and the person that’s required of me in my day to day job. 

 

Anne Helen Petersen: Well, I like that the question asker has a job that a lot of people are like, What’s that job? [laughter] Like product manager? It’s a name that you hear and you’re like, I don’t know what that person does, but I guess that’s a job. And I think that she should take that in mind as she thinks about, oh, I should ask the other people in my life who have jobs that I’m like, I don’t really know what they do and ask them. 

 

Ailsa Chang: Right. 

 

Anne Helen Petersen: What is it that you do? What do you love about it? Like what is animating about it? Right? 

 

Ailsa Chang: Exactly. 

 

Anne Helen Petersen: Because, you know, I think like a thing that really comes forward in her question is. I don’t know what jobs exist. Right. [laughs]

 

Ailsa Chang: Yeah, you just have to information gather. And then also it’s beyond that. And I know this is harder, but I do I do recommend it. You know, you do have to dip your toe a little bit and do the actual work. 

 

Anne Helen Petersen: Yeah. 

 

Ailsa Chang: Maybe either, even picking up a short term internship or a volunteer position, at the very least, shadow somebody. So you can see kind of the day to day drudgery too, you know, because not every job is going to be 100% glamorous all the time. 

 

Anne Helen Petersen: Yeah. 

 

Ailsa Chang: But I feel like it’s very hard to talk about jobs and work in a vacuum. You kind of have to do the thing a little bit.

 

Anne Helen Petersen: Yep. 

 

Ailsa Chang: To test out. 

 

Anne Helen Petersen: So the last part of that question that I just want to address quickly is she says, like, I’m scared of things that require more school. And I think that if she does all of the things that we’ve suggested to try to get a feel for a lot of different jobs, gradually it will become apparent whether or not it is essential to, say, get a credential in some capacity. Right. In order to get your your foot in the door. Like sometimes for people who want to get into tech, like you need to take a coding boot camp of some capacity, you know. But I also think it’s worth talking to people about whether or not that the schooling is necessary. Right? 

 

Anne Helen Petersen: A hundred percent. 

 

Ailsa Chang: Because I think sometimes when we like are interested in a field and especially if we’re high achievers. 

 

Ailsa Chang: Yes. 

 

Anne Helen Petersen: The, the easiest thing to do is like, well, if I just enter a program 

 

Ailsa Chang: Yes.

 

Anne Helen Petersen: That’s the pathway to my job. And it is it is not necessarily the pathway to your job.

 

Ailsa Chang: I am so glad that you brought that up because so many people who self-select into law school have that feel. 

 

Anne Helen Petersen: Yes, yes. 

 

Ailsa Chang: They don’t know what they want to do with their law degree. But law school sounds respectable, it sounds structured. It sounds like you’re not wasting your life if you’re in law school. But I’m glad you said what you said. And because I think if you’re thinking about starting an educational program, you need a question whether you’re you want to sign up for that program because it it assuages your need for certainty. Like if I’m in a degree program, I must be on a track. I must be getting something done. Or are you actually in that program? Because you, you know, it’s a crucial step to where you want to go. 

 

Anne Helen Petersen: Mm hmm. 

 

Ailsa Chang: And I guess that’s what this person is asking. Like, I don’t know. I don’t know. 

 

Anne Helen Petersen: Yeah. 

 

Ailsa Chang: So, yes, definitely collect as much information as you can, because a lot of people ask me like, do I need a J-school degree to become a journalist? And no, you don’t. But I know for me at the time in my life, when I went to J-school, I had that thing in me where I was like, I don’t know if I’m doing the right thing. And I feel like if I go to school, at least somebody is paid full time to teach me to be a journalist. And that feels like more secure. [laughter] And I had the privilege, I had the savings to be able to not work for nine months so I could be a student. And not everybody has that. So I knew I was going to J-school to assuage a need for like taking a concrete step. Though I did learn a lot from J-school and it was a great experience. It’s just not something for everybody. 

 

Anne Helen Petersen: Yeah. 

 

[AD BREAK] 

 

Anne Helen Petersen: Our next question is from Jane, and it’s about explaining the pivot to others. 

 

Jane: I’ve been a social worker since getting my bachelor’s degree in 2014, and I completed my master’s in social work about four years ago. I’m burnt out and have been wrestling with the idea that social work is no longer the field for me for the past two years, I’m planning to make this year my last in this field. And I’m going to be looking for jobs that are a return to the kind of office work I did many years ago before I began my social work career. Things like admin assistant or data entry. How do I explain this significant change in interviews and on my resume or cover letter? And how much should I share about my educational background when it isn’t required or relevant to the position I’m applying for? 

 

Ailsa Chang: I love this question because I am so biased. Like I love it that she’s thinking about swerving and she has all these like different experiences and she’s feeling self-conscious about it. 

 

Anne Helen Petersen: Yeah. 

 

Ailsa Chang: I’m like, oh my God, this is your power. Okay, look, I come from the vantage point of journalism, so maybe I’m different. I love it when I’m interviewing a job applicant who has done different things in their past lives. I think it enriches and deepens people when they have worked in different worlds with different kinds of teams gaining different kinds of skills. They’re just honestly more interesting to me as a potential future colleague right at the outset. 

 

Anne Helen Petersen: Yeah, there’s two schools, I think too, of the like whether or not you need to put your other degrees like the master’s and social work on your resume. Because I know that for myself, who I have a PhD and for other people who have PhDs who are looking for jobs outside of academia, sometimes it’s that signal of like overqualified doesn’t really want to be here or whatever, you know, desperate for a job. But this person, their question says that they have experience in this field, that they’re applying for it. Like, it’s almost like they broke up with someone and they tried a different relationship and they’re like, no, I really love this other place, right? [laughter] Or like moving back to their hometown and it’s like—

 

Ailsa Chang: Yeah. 

 

Anne Helen Petersen: Oh, I needed to have a different experience to realize how much I love my hometown. And so there’s a way to really frame it as I thought that this was something that I wanted to do, but I realized how much I appreciate this type of work, and I have experience in this type of work. And I think that that actually it would signal to me as a prospective employer, this person wants to do this. 

 

Ailsa Chang: Yeah, exactly. This person is choosing to be here because they thought about it. 

 

Anne Helen Petersen: Yes. 

 

Ailsa Chang: I mean, I feel like anyone can relate to that, like any interviewer can relate to that. I think the days are fading now of resumes where someone’s been at the same company for 20 years or, you know, like the IBM man or the GM woman. 

 

Anne Helen Petersen: Right. [laughter] 

 

Ailsa Chang: People move from job to job so much more commonly these days. I would encourage this person to be less self-conscious about explaining the lack of continuity in their resume. I really would. 

 

Anne Helen Petersen: Our next listener has an idea of what her dream pivot would be, but is also wondering how practical it is. This is Lauren. 

 

Lauren: Is it actually a good idea to monetize your passion? I’ve worked in politics for 20 years and I’m completely burned out. I used to love my job but haven’t for about four years. It’s mostly a recession proof field because elections happen no matter how good or bad the economy is. And I’ve worked my way up to the top of my firm. There’s still room for growth, but I don’t want it. I have financial space to figure things out for a bit if my husband keeps his job and good insurance. I want to work at or open a bookstore. It’s still cyclical work and I would still work for or own a small business, but with a completely different schedule for significantly less money. But I wouldn’t be trapped in my house and I would still do client relations and operations management just about books instead of elections. Or is this just a recipe for hating books in 15 years? Does it make more sense to do a smaller pivot and keep the things we love as hobbies instead of careers? 

 

Anne Helen Petersen: I feel like everyone that I know has dreamed at some point about opening up a bookstore. And that isn’t to suggest that this listener’s question is cliche. It’s just to suggest that it seems awesome, but also like something that could absolutely implode. And I wonder if what she needs to do is like talk to some people about small business management right? 

 

Ailsa Chang: Mm hmm.

 

Anne Helen Petersen: Or like, take some small business management. Like, a class. 

 

Ailsa Chang: Yeah. 

 

Anne Helen Petersen: To like, see if that’s something that she feels like she can handle. Because if you have that those tools. 

 

Ailsa Chang: Right. 

 

Anne Helen Petersen: Then it’s far less likely to become this source of burnout and overwhelm. 

 

Ailsa Chang: 100%. I so agree with that. That is very practical advice I was going to give sort of like larger sort of philosophical advice. 

 

Anne Helen Petersen: Yeah. 

 

Ailsa Chang: Because I sort of was struck how she was like, is this a recipe for hating books in 15 years? 

 

Anne Helen Petersen: Mm hmm yeah. 

 

Ailsa Chang: I mean, I just want to clear one thing up. Speaking for myself, I absolutely have days. I have weeks. Hell, I have had months as a journalist where I’m like, I cannot do this journalism thing forever and ever. [laughter] Oh, my God, my life sucks right now. Right. Just because you find passion in your vocation does not mean it will not involve drudgery, headaches, workplace politics. 

 

Anne Helen Petersen: Yeah. 

 

Ailsa Chang: Annoying colleagues, hostile colleagues. All these things that can be very stressful and can, infect, even poison the job. Right? Every job can suck. And it doesn’t mean when it is sucky that it’s the wrong job, it’s the wrong work. So I would encourage this person, like as you’re picking at what to do after politics, like do not approach the universe with this expectation that you are not supposed to ever, ever, ever hate your job. Especially like if the outlook is 15 years. That’s a really long time. Oh my God. Do you books for good years? And if you hate it, if it really comes true that you hate it after a decade and a half, that’s good run. Then you get to do something else. It doesn’t mean you pick the wrong thing just because it lasted only a decade and a half. Right?

 

Anne Helen Petersen: Right. Yeah. 

 

Ailsa Chang: I guess what I would ask more, you know, just emotionally is before you even get to this place where you’re thinking, I need a change. Like ask yourself, are the good days really less than the bad days? Right. Just because you have a bad day doesn’t cancel out the job. I mean, I think it’s more realistic to ask yourself, does the good stuff outweigh the bad stuff? When your bad days do start to outnumber your good days, then you can start thinking about a pivot, but also remember a pivot. It doesn’t have to be a 180, right? It doesn’t have to mean literally jumping. From one professional solar system into a whole other separate solar system. Like just in my career as a journalist, I’ve covered different beats. I’ve gone from criminal justice to politics to economics. I’ve gone from writing long investigations to quick daily turnaround pieces. I’ve been a reporter and now I’m a host of a show that’s literally called All Things Considered, right? [laughter] Like, I’m literally considering all the things every day. And and and down the road there could be an opportunity, I don’t know, to go more into TV or to write a book like I can play with the medium down the road. So what I’m trying to say is like, you can have a career transition, but maybe all you need is a career tweak. And I think we put a lot of pressure on ourselves when we’re thinking about what is the perfect work. We’re trying to come up with this, this singular thing. But a lot of times just making a couple of adjustments or doing different kinds of projects or maybe working with a different team, moving to a different city, doing that same work can be enough to make the work feel good again. 

 

Anne Helen Petersen: Yeah. 

 

Ailsa Chang: And I just I just want to remind people of that. 

 

Anne Helen Petersen: No, that’s such a good point. I think the other thing that you pointed out too, that sometimes work sucks. I think there is sometimes a tendency to think that if I just quit my job, everything will be fixed. 

 

Ailsa Chang: Yes. Yes.

 

Anne Helen Petersen: Right. That’s. But sometimes the problem is more a combination of— 

 

Ailsa Chang: You. [laughs]

 

Anne Helen Petersen: You. And also the fact that work sometimes just sucks. Right.

 

Ailsa Chang: As they say. Wherever you go, there you are. [laughter]

 

Anne Helen Petersen: But but, you know, one thing I was thinking for this question asker is like, what? Especially since they have some financial security. What if they work at a bookstore for a little while? 

 

Ailsa Chang: Yeah, I love that idea. 

 

Anne Helen Petersen: What if they also, you know, talk with the owner of the bookstore about, like, I want to learn how this works. That’s mentorship. 

 

Ailsa Chang: I mean, I don’t even know this person’s interested in a bookstore specifically. I wasn’t sure if she meant book agent. Maybe she wants to be an editor. 

 

Anne Helen Petersen: Oh. 

 

Ailsa Chang: But. But yeah, that’s something that she should explore all the different ways you can get into the book the publishing industry, right? 

 

Anne Helen Petersen: Yeah. Yeah. 

 

Ailsa Chang: Because maybe there’s something that doesn’t feel as different than her work now in politics at this point. 

 

Anne Helen Petersen: Well, and I love to that this person’s already thinking about how she she does client relations and operations management and how like you can do that in many different industries. 

 

Ailsa Chang: Exactly. 

 

Anne Helen Petersen: So maybe it’s not books, but maybe it’s something else. 

 

Ailsa Chang: Exactly. 

 

Anne Helen Petersen: You can transfer those skills that you have that you’ve refined in politics to two different spheres. 

 

Ailsa Chang: Also, like I mean, we’ve said different versions of this, like don’t put so much pressure on yourself to pick your forever thing, right? 

 

Anne Helen Petersen: Yes. 

 

Ailsa Chang: Like, I feel this way about dating men. Like, I never maybe it’s because I’m 47. Like when I meet a new guy, I’m never like, oh, is this the one? 

 

Anne Helen Petersen: Yeah. 

 

Ailsa Chang: I think, like, you move through different seasons of lovers, maybe. And just like, you might move through different seasons of work life, right? 

 

Anne Helen Petersen: Yeah. 

 

Ailsa Chang: I think it’s so much pressure to think you have to commit to the thing, the person, the job for the rest of your life. And. And maybe it will work out that you find the thing that ends up being the thing until you die. Great. Or the person until you die great. But I guess I have now more of this feeling of there’s so much room for growth and change and evolution in one lifetime. My God, I didn’t know myself as a 20 something year old. 

 

Anne Helen Petersen: No. [laughs] 

 

Ailsa Chang: The way I do now is a 47 year old. And if I had to commit to the things that I thought I wanted in my twenties [laughs] it would not be a good life, you know what I mean? [laughter]

 

Anne Helen Petersen: Yeah. Yeah. No, I’m absolutely there as well. 

 

[AD BREAK] 

 

Anne Helen Petersen: Our last question is about what makes a career a career anyways. And this is from Claire. 

 

Claire: I started out working in not for profit arts after university, and I enjoyed it until I started to feel burned out and disillusioned about ever making the kind of money that makes security possible. I then started a masters in journalism. I did well at it, but then, for mostly health reasons, I decided not to pursue the high pressure lifestyle of journalism or media. Now I’ve ended up working in a professional role at a university in a completely unrelated field. When I describe my career path, it feels like a complete mess and a shambles. I feel embarrassed about talking about what I see as a string of failures. I’ve always been a high achiever and I feel like it was expected of me that I’d have a great career. But I feel like I’ve just had a string of jobs. My question is, how do you describe your career to others when you’ve done a lot of pivots and how do you make plans and goals for yourself when the direction seems to be completely random and circumstantial? 

 

Anne Helen Petersen: This is just full circle for us. 

 

Ailsa Chang: Sure is. 

 

Anne Helen Petersen: We’re going back to what we were talking about in the beginning. And so how what would your advice be? I would just love to hear that. 

 

Ailsa Chang: I think it’s a mistake to think about a career as this like unit. 

 

Anne Helen Petersen: Yeah. 

 

Ailsa Chang: Like this one thing right that defines your your whole lifetime or your whole identity. Right. So many people think that my career now as a journalist makes sense given the steps that I took in life from literally law school to the present. Like it all makes sense in retrospect. Only in retrospect. Because, you know, like I said, there’s so much overlap between law and journalism, not only in skill set, but also, you know, lawyers ideally fight for the truth. They are vindicators of justice. Like those are things that you also value in journalism. Like for people who understand my quote unquote “path in life,” it all seems to be like this really logical set of steps. But as I was going through each of those steps, like quitting at the law firm, interning at KQED, I mean, Dad came to visit me at KQED, and he had just seen me at the law office with a view of the San Francisco Bay and a legal assistant sitting outside my office helping me file things. And here now I’m in that in an intern cubicle. I mean, in his mind. I remember watching his face when he visited me at my internship. He just looked so crestfallen, like, what is what is my daughter doing? She’s lost. And at the time, I wasn’t sure if I was lost. Like, I thought there could be a chance I’m lost. So I know, like in the moment, as you’re feeling like you’re jumping from stepping stone is a stepping stone. It can feel like these illogical zigzags. I know that. I know what that feels like. And I would say, just go easier on yourself because— 

 

Anne Helen Petersen: Yeah.

 

Ailsa Chang: —a career can be made up of so many different things. It’s boring to me when I meet someone who has only done one thing or worked at one company or literally had one role their entire life. That’s less interesting to me. And so think of your your life as it stretches ahead, not as a career, but as a string of work experiences that helped you be a fuller person. That’s that’s the goal, isn’t it? 

 

Anne Helen Petersen: I love your point about just being easier on yourself. And I think this is something that, you know, this question asker notes that she is a high achiever. She probably had some notion in her head of what her future path would look like. 

 

Ailsa Chang: Right. 

 

Anne Helen Petersen: But life is full of things that we do not expect. 

 

Ailsa Chang: A hundred percent. 

 

Anne Helen Petersen: And I think that this person is probably a much more interesting and textured person, right, because of the different pivots that she’s taken in her life. 

 

Ailsa Chang: Absolutely. The advice I always give, especially to high achievers, to overachievers, is be prepared to throw out the plan. It’s often with high achievers and overachievers where you you have these people with these very, like, laid out plans and they’re so used to executing their plans. But like I said, like, you know, going full circle when I graduated from law school, finished that clerkship on the Ninth Circuit and got spit out into the real world. I checked all the boxes. I followed the plan. 

 

Anne Helen Petersen: Yeah. 

 

Ailsa Chang: And still you don’t get to that even more important question of what makes you happy. And that’s when the plan. [laughs] It’s so unimportant. And, you know, I will tell this is the last thing I’ll say to this person. I have been asked by Stanford Law School at least three times now to be a speaker. I came back for a reunion one year and another year I was the keynote speaker for their graduation dinner. Another year I was the convocation speaker. I would have never been asked to speak at Stanford Law School I am convinced if I remained a lawyer. That’s what’s so ironic. [laughter] The reason I’m the whole reason I’m interesting now to my alma mater. The only reason that I’m shiny to them and that I have something to say is because I diverged from the path that I dumped the plan, that I did something unexpected that made me to them. Someone who had something to offer in terms of insights. On life. And I just was like, that’s just hilarious, you know? Oh, I had like, a profile in the alumni magazine. I would never be profiled if I was still at the law firm. [laughter] I would just be a dime a dozen. Right? So be different. Be bold. Be different. It’s going to turn out all for the better. 

 

Anne Helen Petersen: Well and I think we should address too that last part of the question about just, you know, she generally feels like it’s difficult to make plans or goals when her career feels random and circumstantial. And I think my advice in situations like this is like, that’s okay. If your job feels random and circumstantial, you know, this is something that we say on the podcast a lot. But like you can make plans and set goals and be ambitious in ways that have nothing to do with your job.

 

Ailsa Chang: Right. 

 

Anne Helen Petersen: So whether that’s like an interest, like volunteering or a hobby or being part of a community, like all of those things can be like, those are the things that you can start to make plans for it. 

 

Ailsa Chang: I love that you’re saying this Anne, because that for me is a new development in my own life, I used to think of ambition as like, you know, you win the awards, you do the big stories, you do like these concrete things. But now I see like ambition is so much bigger than that. You can be ambitious about living a better life, treating the people you love more kindly, treating yourself more kindly, like doing. You can call them hobbies or whatever. Pursuing outside interests like work doesn’t have to be the center of your life to be an ambitious person. 

 

Anne Helen Petersen: Yeah. 

 

Ailsa Chang: You can be ambitious about wanting to be greedier about living the fullest life possible. 

 

Anne Helen Petersen: Yeah. 

 

Ailsa Chang: That is all ambition. So I’m glad you said that because I think we can get so zeroed in on like what is the work that’s going to maximize who I am? Well, there are ways outside of work to do that as well. 

 

Anne Helen Petersen: That is a great place for us to wrap up. So where can people find you on the Internet but also on the radio waves if they want to find you? [laughter]

 

Ailsa Chang: Okay. Well, on most days I start going live at 4 p.m. Eastern on a show called All Things Considered on NPR. And everybody, wherever you live, you all have different radio stations that tune into NPR. But usually I’m on 4 p.m. to 6 p.m., depending on what time zone you are. But you can also find me on Instagram, Twitter, Facebook, all the places. 

 

Anne Helen Petersen: I’ll say that you’re my companion from around 4:30 until 5:45 every afternoon. 

 

Ailsa Chang: Oh cool. 

 

Anne Helen Petersen: While I prep for dinner and just like piddle around the house. So that is it’s been a real pleasure and delight to have this conversation. 

 

Ailsa Chang: Oh, thank you. Likewise. [music pays]

 

Anne Helen Petersen: Thanks for listening to Work Appropriate. If you need advice about a sticky situation at work, we’re here for you. Submit your questions at WorkAppropriate.com or send a voice memo with your question to Work Appropriate at Crooked.com. Some episodes we’re working on include problems with taking a much needed vacation, juggling parenthood with work, and making caring professions more sustainable. We are taking a break next week. There are like 30 different people that are descending upon the island where I live and we’re going to all hang out and it’s going to be wild and crazy in like the, you know, we’re 42 sort of way, but we’ll be back July 12th with an episode all about working while disabled. Be sure to subscribe so you don’t miss it. And in the meantime, follow us @CrookedMedia on Instagram and Twitter for more original content hosts takeovers and other community events. You can follow me on Instagram @AnneHelenPetersen and you can sign up for my newsletter Culture Study AnneHelen.substack.com. And if you like the show, leave us a review on your podcast app of choice it really helps. Work Appropriate is a Crooked Media production. I’m Anne Helen Petersen, your host. Our executive producer is Kendra James. Melody Rowell is our producer and editor. Alison Falzetta is our development producer. Music is composed by Chanell Crichlow. Additional production support from Ari Schwartz and a special thanks to Katie Long and Sarah Geismer. [music plays]