The Worst Parts of Job Searching with Phoebe Gavin | Crooked Media
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September 27, 2023
Work Appropriate
The Worst Parts of Job Searching with Phoebe Gavin

In This Episode

We’ve done episodes on pivoting careers, on starting over, on starting a new job— and now it’s time to talk about the absolute slog that is searching, applying, and interviewing for a new job. Phoebe Gavin, career coach and founder of Better with Phoebe, joins host Anne Helen Petersen to give listeners advice on getting through the slog and landing the job you want.

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Anne Helen Petersen: Hi, everyone. I’m Anne Helen Petersen, and this is Work Appropriate. [music plays] I want you to take a minute here and think about your experiences with job hunting. Like actually pause. And think about it. When I do it, I get these flashes of memories of awkwardly handing over printed resumes at various restaurants and coffee shops, of cold emailing and scouring job listings in like the alternative weekly of trying to pick out the right outfit for an interview and realizing as soon as I showed up that I definitely, definitely chose wrong. I have memories of applying for every single academic job in my field and getting one call in return. And scratchy ill fitting wool blazers that I thought looked professional and trying to figure out what to do with my hands. How do I cross my legs? Feeling like every call could be a hiring manager there to tell you that your life was about to change. But the call just never comes. [laughs] Honestly, the only memories that are more cringe and anxiety inducing involve being an eighth grader. Now I say all of us and encourage you to remember all this so that we can collectively muster some real empathy for what it’s like to try and find a job right now. Maybe you are trying to find a job right now. Maybe you don’t need to look in the past at all to feel cringe and anxiety. It’s right there with you. And it’s not just because the economy is weird, but because in many cases, the job application dance is just so much more complicated and prolonged. There’s more interviews, like a lot more interviews, more interviews than you could possibly imagine just for one job. And then the spread of remote work also means that there’s a lot more jobs to apply to and a lot more people in the applicant pool. We’ve done episodes in the past on switching industries, but we wanted to have an entire episode dedicated to the slog of job searching today, and we knew exactly which co-host to ask back to help us. [music plays]


Phoebe Gavin: My name is Phoebe Gavin. I’m a career and leadership coach, helping ambitious professionals build successful, fulfilling careers without sacrificing work life balance and everyone. 


Anne Helen Petersen: You should go back and listen to the other episode that we had Phoebe on because she is fantastic and listeners loved her and we’re so grateful to have her back today. Let’s talk about how you figured out all of the nitty gritty of job searching for yourself. Like, how did you get to the point where you’re like, I can help other people do this? 


Phoebe Gavin: I had a mentor, and it was actually incredibly important for me to have a mentor very, very early in my career. So I come from a low income background. I joined the military out of college. My mom was a cleaner. My dad is a plumber. There are no white collar professionals in my immediate family. And so I joined the military to pay for college. And then once I got out of the military, I was dealing with sort of PTSD from that also in school, also trying to figure out how do I do this like internship thing at these like corporate companies. [laughter] Do I need to wear a suit and all of that? 


Anne Helen Petersen: Yeah. 


Phoebe Gavin: And the career center at my college was really important. And also I was volunteering with a veterans organization that had also had a career support program. And because I was volunteering with them, I had more access to them than their members normally would. 


Anne Helen Petersen: Yeah. 


Phoebe Gavin: And I ended up building a strong relationship with one of their program managers who became my mentor. And not only did he save my life because I was really struggling mentally. He also set me up to be much more successful than I would have been if I would have just sort of figured it out on my own as a first generation knowledge professional. And that was so important for me that it became really central to my vision for myself was to always find ways to help other people grow as I was growing. And then early in my career, that didn’t look like very much. But as I built my career, got more support and more knowledge from other mentors, including the original one, and started building my own career and starting to hire for myself and making strategic decisions on behalf of organizations for myself. I was always looking for opportunities to support people in that way, and so mentorship was extraordinarily important, but also being proactive. And I was a mega Googler trying to ask every single question and trying to figure everything out. So it was about mentorship and being really proactive about research. 


Anne Helen Petersen: I feel like sometimes job searchers and I understand why this is, there’s a bit of pride where people don’t want to use the structures that are available to them, either in the form of career services at their institution, or they don’t want to ask for help within their existing networks because it feels almost shameful, right? Like that you would need help looking for a job. It’s one of those things, and I think this is very American, that like I can figure out how to look for a job the same way that like I can figure out how to become middle class [laughter] on my own right, when in reality that is the way that it happens for very, very few people. So how do we get over ourselves and and ask for more help. 


Phoebe Gavin: Realize that the only thing that you’re doing is hurting yourself. 


Anne Helen Petersen: Yeah. [laughs]


Phoebe Gavin: When you ask for help, you will either get help or you will get good information about the person that you asked for help from. 


Anne Helen Petersen: Yeah. 


Phoebe Gavin: And so at the very least, you’re going to know, okay, that is not someone that I can depend on for support. But the best case scenario is that someone could really help you move forward. And if I hadn’t asked for help of that mentor, if I had of just continued to struggle both with my mental health and my getting myself professionally established, I would probably be dead like that is how serious it is when you are trying to solve all the problems yourself and not asking for help, ask for help. 


Anne Helen Petersen: Yeah. 


Phoebe Gavin: And often you will be surprised, especially the last few years, where there have been so many layoffs and people have been asking for help more publicly. 


Anne Helen Petersen: Yeah. 


Phoebe Gavin: That complete and total strangers will reach out to provide some sort of support, the support they feel comfortable providing, not knowing you or expecting anything from you at all. And so asking for help is the best thing that you can do to move forward with your career. 


Anne Helen Petersen: What else do you see job seekers struggling with right now? 


Phoebe Gavin: Not taking the time to understand the difference between information and assumptions? I spend most of my career coaching sessions either managing emotions or managing assumptions because work is emotional. It is a human experience. The human experience is an emotional experience. Work is an emotional experience. And so we’re trying to navigate workplace problems and career problems. Those are emotional problems. And then the other piece is that those emotions often push us to make assumptions about ourselves, about our situations, about what’s possible for us, about the potential outcomes. If we make certain decisions, we take certain actions. And often those assumptions are either. Unfounded, uninformed, completely wrong. Sometimes they’re right, but it would be better to know that it’s right because it’s information, then because you invented a story in your head and then went down the entire logic tree off of an assumption instead of information. 


Anne Helen Petersen: Yeah, I’ll say that. Where I see this most vividly is people who are in industries and who have been told or implicitly come to understand that like I don’t have any skills outside of my industry. 


Phoebe Gavin: Yeah. 


Anne Helen Petersen: It’s hard because part of the reason you’re told that or come to understand that is to keep you within that industry, even when it’s hurtful to you for any number of reasons. But it’s hard to know what your skills are, what that looks like. And we have whole episodes that are about like figuring out, okay, I’m good at this job, what other jobs could I be good at? But, you know, when I was in high school, we took one of those, like, very old school tests where it, like, basically figures out what your what you have aptitude for, like what jobs you would be suited for. 


Phoebe Gavin: Yeah. 


Anne Helen Petersen: And I feel like there’s no contemporary version of that. Right. Because the jobs that they were selecting for back then and in my high school in particular were very much like stuff in the trades. And they’re I actually think [laughter] I would be probably really good at a lot of those things that I had aptitude for. But now it’s like, how do I take all of the skills that I have as an academic and then transfer those into things that like. In jobs that I don’t even know what they are. And that’s the thing, at least that I see the most often. I don’t know. What do you see? 


Phoebe Gavin: I see folks looking for those sorts of tools and they do exist. 


Anne Helen Petersen: Yeah. 


Phoebe Gavin: And treating the one output it gives you as the gospel. 


Anne Helen Petersen: Ah. 


Phoebe Gavin: The thing has told me what I can do, and this is what I can do. 


Anne Helen Petersen: Right. 


Phoebe Gavin: I can’t do anything else. And these are the only options. And so I need to choose from this menu that this computer program has given me. 


Anne Helen Petersen: Yes. [laughs]


Phoebe Gavin: That’s what I have access to. And that’s definitely not the case either. Those sorts of tools are certainly helpful data points, but I do find that I will sometimes get a new career coaching client in and they’ll send me like the PDFs of all of the personality tests that they’ve gotten. [laughter] And it’s like, I’m so glad that you use that as a tool to to understand yourself. And I’m looking forward to digging into it as well. But we are going to put this on the shelf. 


Anne Helen Petersen: Yeah. 


Phoebe Gavin: We are going to talk about who you are as a person right now outside of the construct of Myers-Briggs. 


Anne Helen Petersen: Yeah, I love that. Okay, so our questions today are super practical, so we’re just going to jump in. The first question is from Hannah. 


Hannah: I want to find a job that I love that pays enough to pay the bills and food, etc. But I’m really struggling to find the time and energy and motivation, mental capacity to job hunt. Whilst I’m working full time and running my Brownie and guide units and everything else life involves how to navigate this. 


Anne Helen Petersen: All right. So first off, I love that she mentioned that running her Brownie unit is actually taking up a lot of her time because I sometimes think that people like, forget to talk about like, oh, the other thing in my life that is making it hard to do this thing is a thing that is valuable. So I think it’s awesome. So I think we hear this a lot of like looking for a job is a full time job. What advice do you give Hannah here? 


Phoebe Gavin: I love the point that you just made before I jump into my actual advice [laughter] which is your personal life also matters. 


Anne Helen Petersen: Yeah. 


Phoebe Gavin: And if you are having a hard time prioritizing job seeking the way that you would like it is okay if some of that time is going toward the things that are meaningful for you. And I’m assuming that this respondent is mentioning the Brownie unit because it’s really important to them. 


Anne Helen Petersen: Yeah. 


Phoebe Gavin: And so I want to answer it in a way that doesn’t force this person to downsize their Brownie time. 


Anne Helen Petersen: Yeah. 


Phoebe Gavin: Because that’s important enough for them to put in the question. And so it’s important enough for us to take into account. 


Anne Helen Petersen: Yeah. 


Phoebe Gavin: And the top line is that you have to break it up into the smallest possible pieces. Getting a job is a gigantic multiple week, multiple month process. And if we think about that project all at once, it becomes very overwhelming. 


Anne Helen Petersen: Mm hmm. 


Phoebe Gavin: But if we break it into the tiniest possible pieces, there are things that you can do in single digit minutes that help you move forward on the big project of getting a job. And when you have a lot of competing priorities, a lot of stakeholders in your time, you may not have the luxury of devoting big time blocks to the project. You may have to spend smaller windows on it. But the most important thing is to do one thing and to complete it. I have a, an analogy that I use is build the bridge all the way over the chasm. 


Anne Helen Petersen: Mm. 


Phoebe Gavin: You’re trying to accomplish something, fully accomplish that one task before you move on to another task, because if you’re bouncing around, you’re building a bunch of half bridges and you’re not actually making progress on anything. And so for this individual, I would encourage them to sort of take a step back and do an audit of their time. When I think about work, when I think about my Brownie unit, when I think about the other priorities that are really important for me in my life, I see this amount of time available distributed across my week to put toward my job search. And when I think about all of the things that I could do to move forward with my job search, the top priorities are thing A, thing B, thing C, and I can break those into small enough pieces where 5 minutes here or 15 minutes here, a half an hour here, an hour here on a on a Sunday night. I can get some of these things done. The flip side, sort of the trade off is that if you’re working in smaller pieces spread over a longer period of time, that does mean your job search is going to be longer. And so if that tradeoff is too uncomfortable, ask for help. Are there other people who might be able to support you temporarily or permanently in these aspects of your personal life that are currently competing with your job search? Because you’re not going to be searching for a job forever. 


Anne Helen Petersen: Yeah. 


Phoebe Gavin: You’re going to be able to go back to fully committing to the things that you’ve committed to now. But if there are any people who can help you with the Brownie unit just temporarily while you’re doing the job search or with the other aspects in your personal life, that can be really helpful. But also maybe there’s room to set better boundaries at work so that it’s not following you into your personal time. And more of your personal time is available for both the Brownie unit and your job search. 


Anne Helen Petersen: One thing I’ve heard from people is that they are very good at looking at job listings and. Not very good at finishing the applications. Right. It’s kind of like dating. Like, you’re like. 


Phoebe Gavin: Yeah. 


Anne Helen Petersen: I’m I’m really into looking at everyone’s profiles and less good at going on the dates. [laughter] And I like your advice. Like, you got to follow through. Like, don’t just make the spreadsheet with all of the jobs. That’s the fun part. Almost, right? [laughter] Like, you got to make this. Like, that’s step one, but then, okay, boom, boom, boom, boom. Put that into little like consumable or manageable bites of got to get my resume into this. And, and it’s true that every job requires tinkering, it requires specialization. But if you break it into those smaller pieces, I think it’s really possible. 


Phoebe Gavin: And it’s also important to like find the things that you’re doing repeatedly and see if there’s a way that you can do it more efficiently. You know, my I don’t didn’t think of in my dating days. I did not think of a special message for every person I ask every single person what they’re reading. If they weren’t reading books, they weren’t a good match for me. [laughs]


Anne Helen Petersen: Yeah. 


Phoebe Gavin: And so finding that that took the pressure off of, you know, how to do that first step because getting started is always the hardest part. And so what are the templates that you can use? What are the guys that you can use to support you in this? And this is another opportunity to ask for help. If there are people who, you know, who are also looking, maybe you can crowdsource the effort of figuring some of these things out or reading them through, making sure that they’re doing the best possible job. And certainly a mentor or a coach can help with that as well. 


Anne Helen Petersen: Yeah, like having someone who can be your proofreader, having someone who can like just keep an eye out, right? Like have an alert on or something like that. But I also really like the point that you made that you can draw on your support, like your support structure to make some time for this because this is a huge important thing. It’s not the same as an illness, it’s not the same as a crisis, but it is a big life thing. And if you were moving, you would feel like you could ask people for some help. 


Phoebe Gavin: Yeah. 


Anne Helen Petersen: And so maybe to think of it something like whether that’s if you have kids, like can I have some help with childcare for a day or with your current job? Can I take a day off? Like, can I use one of my PTO days, which like that’s hard and I think that’s not a great equation, but maybe that’s what you need to get started is that one free day.


Phoebe Gavin: But if you’re leaving and you’re going to lose those PTO days anyway. 


Anne Helen Petersen: [laughter] Depending on the state where you are, especially if you have a limited PTO then use it. [laughter] Right.


Phoebe Gavin: Yeah. 


Anne Helen Petersen: All right. So that’s a great segue right into our next question, but it’s about still doing your current job well when you want out. Let’s hear from Beth. 


Beth: I’m an early career physician and I’m miserable. This system is broken beyond repair such that any singular doctor is absolutely useless in trying to make any changes for the better. But as a mom and a partner and frankly a human with other needs and desires, I’m seriously contemplating leaving medicine all together. I know it will take time, years, even for a new non-clinical path to take shape. And yet I’m worried about my job in the meantime, because I really, really need it. But how do I avoid my colleagues finding out? Will they assume I’m not dedicated or working hard enough? And what about my patients? How do I balance planning and researching a career shift while continuing in this job that is slowly killing me, but in which I’m absolutely deeply and painfully stuck? 


Anne Helen Petersen: Oof now, this is a horrible feeling and knowing that you’re done and that you want out, but you can’t actually leave yet knowing that the relationship is over. But like, for whatever reason, you can’t leave yet. So I think we can address this in parts first. How can Beth throw herself into figuring out this new career without her current colleagues finding out? 


Phoebe Gavin: Actually, let me start a little bit further back then that. 


Anne Helen Petersen: Yeah. 


Phoebe Gavin: Why does Beth think that it’s going to take years? Remember at the that top of the episode we were talking about, like assumptions and then people go down a really long path of assumptions. Beth is assuming that is going to take years. 


Anne Helen Petersen: Yeah. 


Phoebe Gavin: For her to put her next career together. And maybe there is some context that we weren’t able to get in the brevity of the question that makes that a reasonable assumption. But from my professional opinion, I don’t think that’s a reasonable assumption. Years, multiple years, that’s a really long time. And a career transition can definitely happen in a shorter period of time. The additional assumption is if your colleagues find out that matters [laughter] in any way, your colleagues don’t have to live your life. You have to live your life. 


Anne Helen Petersen: Yeah. 


Phoebe Gavin: You are the one who has to live every day with the consequences of your decisions. And if you’re making those decisions based on the way that your colleagues or really anyone is going to think of you or how they might react to you, then you are living for someone who is not living for you. 


Anne Helen Petersen: Yeah. 


Phoebe Gavin: Those colleagues are not out there thinking, Man, I wonder what Beth thinks about how I spend my day. [laughter] But Beth is thinking that about these colleagues and it’s keeping her from taking the action that she has to take. 


Anne Helen Petersen: Yeah, yeah. 


Phoebe Gavin: To move her self out of a career that she is killing her, that she hates, and into a career chapter that is better suited for her needs. And so all of these assumptions are things that I would want to pull out and say, tell me more about this. Why do you think this? 


Anne Helen Petersen: I sense that Beth is a people pleaser. 


Phoebe Gavin: It’s possible. 


Anne Helen Petersen: And and has created is sensing feelings of obligations and like that. She would let people down. Just as a funny side note, I was working for I was a nanny for a doctor who wanted to quit. And I one day I had to get a hold of her to ask her a question about something. And this was pre cell phones. So I called her office and on on the answering machine it said like, Doctor so-and-so is no longer taking patients as she prepares to leave the practice to like to stop being a doctor. And she hadn’t told me yet as her nanny because when she stopped being a doctor, she was not going to need my services anymore. And so it actually created this weird situation where because she hadn’t told me of her plans and I was dependent on her, it was not a great situation. It turned out fine. But like she should have told me as well when she made that public to her workplace, this is not that situation. Right? She’s talking about her colleagues. She’s not talking about anyone whose job is contingent upon her. So I think that you’re totally right that, like no one else is spending their days thinking about how Beth is spending her days so she can liberate herself a little bit from that that fear. 


Phoebe Gavin: And that’s not to say that they wouldn’t have opinions about it. 


Anne Helen Petersen: Yes. 


Phoebe Gavin: If they found out in a very clear way that she was on her way out. But those opinions don’t only matter as long as you have to work with those people and you have to work with those people for as long as you’re doing everything else other than moving yourself into another professional situation. So it’s worth it to invest in yourself and to make those decisions and risk the possibility of people finding out that you’re interested in moving into another direction and then dealing with the consequences of that. Because on the other side of those consequences is a better life. 


Anne Helen Petersen: Yeah, what if we’re reading this slightly off? And what if Beth is worried that her colleagues will say, Well, if you don’t want to be doing this job, like you should get out of here, kind of like a more aggressive reaction. Do you sense that at all or do you have any advice on that? 


Phoebe Gavin: I don’t sense that, but it does happen. But it’s very rare. It’s very, very rare. If you are working in an industry that is highly competitive, an industry where there are lots of trade secrets and corporate espionage the difference between millions and billions [laughter] then those sorts of things can happen. You know, certainly if you’re working in consulting, that can be a big challenge. But it’s challenging for me to see that as a real risk to where a real threat to where it needs to change the way that she approaches her job search. Some people can be. It depends on the relationship with the organization and the relationship with your supervisor. Some people can be very straightforward and say, I’d love to talk to you about succession planning. I think that my time in this role is coming to an end. I know there aren’t opportunities within the organization that meet my needs at this time, but I want to make sure that everyone has a really good off ramp. And this is a timeline that I’m looking at. Does that timeline work for you? Some people can do that, some people can’t. But it is an option and it really depends on your comfort level, what kind of work you’re doing, what kind of organization that you’re in. But if that is genuinely concerned that she’s going to get pushed out, if she if her colleagues find out that she is looking, they are probably not actively spending time trying to figure out whether how long everyone is going to be staying in the organization. And so it’s just a matter of having some discretion, especially as it relates to networking. And since she’s looking to leave medicine, she doesn’t need to have discretion in terms of what kinds of company she’s applying for because she’s going to be moving into a different industry. But if that wasn’t the case, if she was looking to stay in medicine and move into a different role within medicine or a different space in medicine, then she would need to have some discretion in terms of what kinds of companies that she’s applying for so that things don’t move around. And it’s certainly the case in industries that are very small where there’s lots of sort of poaching and people moving all around. But in this case, and she’s looking to move into another industry, that discretion might not be necessary. 


Anne Helen Petersen: How do you think she can stay, as she mentions in the question, stay engaged in her current work and keep doing a good job when she’s spending more of this mental energy figuring out how to leave. 


Phoebe Gavin: This is a situation where outsourcing could be really helpful given that, you know, this individual is a physician. I’m assuming that they have a bit of financial flexibility where they can invest in themselves and that they have some money that they could put toward their career and that the time is the resource that is as scarce as possible. Outsourcing some of this work is a really great idea. I am generally not a fan of engaging resume writers because they don’t build your skills. 


Anne Helen Petersen: Mm. 


Phoebe Gavin: Get a thing, and then the thing is only useful for the time that you’re using it, and then you don’t actually have the skills to update it for the next time you need it. 


Anne Helen Petersen: Write. 


Phoebe Gavin: This is a situation where I would send her all full force. Go get you a resume, writer girl. Go get someone who can support you in creating these materials, who can support you in collecting these materials. You know, look into a VA service who might be able to, actual human, who can find more of these listings and assess them against particular criteria, work with them over time to refine that so that the list that this individual provides for you in support of your goals is truly worthy of the scarce time that you have to make these applications move forward. There are lots of people who don’t have that privilege, but if you do have the benefit of some finances that you can put towards solving your career transition problems, it makes sense to make that investment. It doesn’t necessarily need to be a career coach. You know, obviously as a career coach, I have a vested interest in this advice [laughter] but being the right support for you In terms of investing and support. There are lots and lots of places where you can find that support. 


Anne Helen Petersen: Yeah, like spend some money on finding someone who can like do the fonts for you. You know what I mean? Like, if that’s going to be a big weight, so many people I know, especially in jobs where they’ve never had to necessarily like apply in a traditional way, which is often the case in a situation like this, like they’re they’re just so overwhelmed by the prospect of like finding a resume template. And that’s something that you can outsource. 


Phoebe Gavin: I love Etsy. Etsy has great resume templates. 


Anne Helen Petersen: [laughs] Yes. 


Phoebe Gavin: They’re pretty, they’re attractive. Some of them are too attractive where they don’t actually make sense for applicant tracking systems. 


Anne Helen Petersen: Yes, yes. [laughs]


Phoebe Gavin: But I, I have a like a little list that I send to my clients. Like check these out if you like any of them. Buy that and fill in the blanks. You don’t need to put a bunch of mental energy into choosing googling font pairings. 


Anne Helen Petersen: No, no, thank you for the specific advice because I feel like that’s a place where people, if they weren’t necessarily frequenters  of that world, wouldn’t know that. That’s the place where you go and get resume templates. Now it doesn’t have to be Microsoft Word. 


Anne Helen Petersen: Our next question is like, the thesis of this entire podcast is, so I’m glad we get to address it head on. This is from Kayla and our producer. Melody is going to read it. 


Kayla: I’m going to be on the job market soon and my question is, what makes a good job? What are some standards I should be looking out for regardless of my industry? 


Anne Helen Petersen: There are so many places we could start. Phoebe, you go first. What do you think? 


Phoebe Gavin: [laughs] Well, this is a really hard question to answer, because everyone’s different. 


Anne Helen Petersen: Right, right. 


Phoebe Gavin: Depending on your personal preferences, your life stage, your industry, the differences in what makes a good job are massive. 


Anne Helen Petersen: Totally. 


Phoebe Gavin: I think one thing that is universal is respect for your humanity. 


Anne Helen Petersen: Yeah. 


Phoebe Gavin: Some companies just see workers as the means of production and as assets rather than actual human beings. But there are lots of ways that a company or a leader can show respect for the humanity of the workers. And what makes me feel seen and respected might be different from what you would think makes you feel seen and respected. For example, I am a work introvert. I don’t like to share a lot of my personal stuff in in work situations. I don’t want work friends, and that is a real perk for a lot of people. 


Anne Helen Petersen: Yeah. 


Phoebe Gavin: And so there are differences. I think what I would do is encourage this person to ask themselves a few questions. Imagine what it looks like when work sits comfortably in your life. What does that actually look like when work gives more to your life than it takes? There are going to be some characteristics that come up. Write those down. Don’t do it in your head. Write it down. If you could design a working dynamic with your colleagues and your supervisors. What would that look like? Write it down. Where do you sit on the work life balance spectrum? Are you a separator or are you an integrator or are you somewhere in between? Do you need work to be a source of meaning for your life? Or do you want work to make space for meaning outside of work? And if you are able to take some time to think through those things and write them down, don’t do it in your head. Please write it down. That is going to help you identify some characteristics around standards that are accustomed to you versus the ones that work for air quotes, “everyone.”


Anne Helen Petersen: Yeah, I feel like in some ways this advice might seem facile, but it’s. I think she should journal about it [laughs] like this is what you’re suggesting right is like you need to talk to yourself. And maybe that means you need to talk to a friend first to get to consolidate some of those ideas. Some people are real external processers in that way. And then some people like me like, I don’t know how I feel about something until I’m forced to write it down. And oftentimes, particularly in my own, like write it physically in my own handwriting [laughter] because, you know, as many people know, the time it takes for you to actually move the pen or the pencil on the page is the time, like your brain is catching up with it and thinking about it. And so I think that that is just fantastic advice for actually figuring out what a good job looks like for you. And the other thing that I would emphasize and you touch on this is like you might be you also should figure out what type of job are you looking for at this season in your life. 


Phoebe Gavin: Yeah. 


Anne Helen Petersen: Maybe you are looking for a job that’s going to consume you. Maybe that’s what like you just you want to feel absolutely dedicated to your job for this period in your life. Maybe you’ve been in a job like that and that is the opposite of what you want. You can be honest with yourself. Instead of trying to, like, replicate a different sort of job that you’ve had in the past or a job that you’ve seen others have or that sort of thing. Like what kind of job are you looking for? And that will give you some leeway. And I think too, that you can be honest with the fact that, like maybe if I’m looking for a ton more flexibility, then I can’t also look for the highest pay scale. There are gives and takes. [laughs] 


Phoebe Gavin: There are definitely some tradeoffs, but I completely agree with you on the importance of writing it down, which is why I send so many of my clients worksheets all the time. 


Anne Helen Petersen: Yeah. 


Phoebe Gavin: Sometimes they get they get annoyed with me, like, I just want to talk about it. Like, I understand that you want to talk about it, but that’s not actually going to be helpful for you. We’re not going to be able to look at our conversation and then use that as criteria. But if you write something down and you get your thoughts out of your head and onto paper, then you have that reference. I love a whiteboard. I’m a whiteboard person. I’m not a journal person, but I am a whiteboard person. And when I whiteboard it out and I can erase and cross out and use different colors and do all of those sorts of things, it really helps me, especially as a person who with ADD goes in every single direction cognitively, it really forces me to complete entire thoughts and get them onto the whiteboard and then analyze them after they have been completed. And that analysis is often where people get caught up when they’re doing it in their head. They’ll think, Oh, I’d like some flexibility. Oh, but that means I’m not going to be able to take as much pay as I would like or I’d have to switch industries. Or what if they change their remote policy at the last minute and we don’t need to think all of those things through. We need to write all of those things down and then think them through separately and independently. 


Anne Helen Petersen: Right and prioritize there. We get a lot of questions from people who maybe like one of their priorities is good health insurance or parental leave or PTO time, but also feel like it’s just totally inscrutable. What are companies offering in terms of those sorts of benefits? Until you get to the point of nearly getting the job? And I wonder if your background here can maybe help us think about like, how can you suss those things out when you’re on the job? 


Phoebe Gavin: Yeah, that’s a challenging one. If you are looking to work for a large company, I definitely recommend spending some good old time on Glassdoor. 


Anne Helen Petersen: Yeah. 


Phoebe Gavin: Glassdoor is flawed, but one of the things that it is really helpful for is assessing what the benefits are a bit more accurately than you would if you’re just kind of digging through the company website. And certainly more accurately than if you are asking a tiny, vulnerable question at the beginning of the application process. 


Anne Helen Petersen: Right. 


Phoebe Gavin: And so that can be a really great way to do it. If you’re looking to work at medium to large organizations where there are going to be a lot of Glassdoor submissions for the company, but otherwise it’s not something they actually have to disclose. Hopefully that’s something that changes in the future. 


Anne Helen Petersen: Yeah, and it’s so hard, right? You’re like, all I want to know is can I have a baby? Right? Or all I want to know is like, what insurance plan you’re on? I do. I have a friend who did this kind of like, I wouldn’t say sneaky did it in sort of like a different way. Was just found someone in their larger LinkedIn network who had recently left a job and really just said, like, can you tell me what insurance plan you guys had? 


Phoebe Gavin: Oh, my gosh, that’s genius. Stealing that. [laughter] That’s so smart. And, you know, if the person is and I love that this friend of yours asked someone who had just left the company because they don’t have any vested interest in—


Anne Helen Petersen: No. 


Phoebe Gavin: —protecting the companies information. 


Anne Helen Petersen: And maybe they’ll say something else interesting, right? [laughs]


Phoebe Gavin: Exactly. And it’s also one of those things where if you are asking someone who is sort of early career or mid-career, they don’t get questions about their career, they haven’t gotten to the point where they are, you know, splashy and glittery, where people want to talk to them. And so the likelihood of getting a response is really high. And so I think that’s such a genius idea. I’m stealing it. [laughs]


Anne Helen Petersen: Well, and especially like, let’s say you maybe want to have a kid at some point in the future in a time span when you would optimally be in this job. That’s something where you definitely want to talk to someone who’s also had a kid who’s been at that organization in some capacity and like there are sneakier ways that you can do that while you’re in the job interview process of being like, Oh, can I talk to like, is there a new moms interest like affinity group? But also talking to someone who’s left the company about the honest expectations of people in and out of parental leave would be really interesting and and useful. But that’s also getting the horse in front of the cart a little bit. If you just need to know, can I still go to my doctor? Is the insurance coverage decent? Those are quick and easy questions that you can ask someone on LinkedIn for sure. 


Phoebe Gavin: Yep. 


Anne Helen Petersen: Our next question is from Suvie, who is looking to make a pivot. 


Suvie: So I’ve been a researcher in the nonprofit sector for 13 years. I’m no longer passionate about what I do and would like to make some money, but I have no idea what kind of job my skills are transferable to or what industry I might be interested in. Who could I talk to who knows enough about the job market in different industries? Who could look at my resume and say, Your skills are transferable to X job in Y industry making Z amount of money? And here’s how you pivot. Is there a person who does that? I’m using a career coach currently, but they aren’t really doing that for me. Should I be looking for a career transition coach? Does that even exist? Thank you. 


Anne Helen Petersen: All right. So first I want to plug our episode about pivoting with Ailsa Chang, but also figuring out the options for a pivot can be very daunting. And also, I think sometimes we don’t understand exactly what a career coach can do. So I want to talk a little bit about that first. So, Phoebe, what do you think? Is this in your wheelhouse? 


Phoebe Gavin: So obviously, I don’t know who this person is or who their career coach is. And so I don’t want to criticize their current coach. And I also can’t speak to their specific situation. But I’m I’m assuming that this description is sort of a highly simplified version of what they want. For the sake of brevity, for the question. 


Anne Helen Petersen: Yeah. 


Phoebe Gavin: Because I don’t know of anyone who has a comprehensive enough understanding of the entirety of the US economy [laughter] to be able to provide this person with this information based off of a one or two page resume, also a one or two page resume. That’s not what it is designed to do, is designed to get you an interview. It’s not even designed to get you a job. 


Anne Helen Petersen: Right. 


Phoebe Gavin: And so a resume is not going to be a good tool for designing a career pivot. And so when you think about working with a career coach and or exploring the idea of working with some sort of investing in some sort of career support service, it’s really important to be clear in your own mind about what problem you want to solve and what success looks like for you. 


Anne Helen Petersen: Mm. 


Phoebe Gavin: And then what the career coach does is comes in and helps you understand what is the path that is going to get you from where you are now to where you want to go. And that career coach is going to walk with you through that process so that you are supported through the entire experience. That is not to say that the career coach is going to do all of the work for you. You’re going to have to do a lot of the work to figure out some of the answers to these questions. A good coach is going to be well positioned to understand your needs and to read between the lines and to change things up. If things change, to make sure that you’re always in alignment. But they’re not going to be able to do the work for you. And even if they did, they don’t know you or your history as well as you do. I have clients that I’ve worked with for years and I don’t know them as well as they know them. 


Anne Helen Petersen: Mm. 


Phoebe Gavin: We’ve had conversations. We’ve had maybe eight or 10 hours of conversations. They have been living their actual professional lives and so often I give them homework of I want you to think about these questions and then let’s look at the answers together so that we can figure out what the best move is as far as getting you to where you want to go. But a career coach is not like a career strategy ATM, or like a career repair man where we pull up our manual and say, okay, these are the things, this is the tool that we need and turn the wrench 45 degrees. It just doesn’t work that way because people are really unique. And so it’s more like working with a doctor or a therapist because people are very complicated, careers are very complicated. And so it requires quite a bit more nuance than we have in our question today. 


Anne Helen Petersen: You got to do the work yourself, too. Like you got to do that homework. You know, you call it like homework worksheets. Like you got to do that work before you can figure it out. Job seekers are not the same as dogs, but if you bring your dog to a dog trainer, the dog trainer does amazing work, but then they give you the dog back and it’s like, now you got to do this work, right? [laughs] Like you have to continue these practices and this mindfulness and you got it like put in that that labor yourself. And I don’t think that our question asker is like expecting the career coach to do all of the work for them. But I do—


Phoebe Gavin: Well I have ended up in consultations with folks who wanted similar things or wanted that much sort of simplicity and ease in the process. And man, if there someone listening who knows how to do that, like please contact me. [laughter] I would love to learn from you. I will apprentice. Unpaid internship. Unpaid internship [laughter] because it’s a lot messier than that. But one thing that I do want to note is that, you know, this person is already working with the coach and the coach. They’re not getting what they want out of that coaching experience. You are paying this person to help you solve a problem If they are not helping you solve that problem the way you want it solved, tell them. 


Anne Helen Petersen: Yeah. 


Phoebe Gavin: Either that coach is going to say, okay, well let’s take a step back. Let’s figure out what needs to change so that your needs can be met. Or they’re going to say, It sounds like the problem that we came in to work together to solve has changed or is now is outside of my wheelhouse. We might want to sunset our relationship and transition you to somebody who can support you in the way that you want to be supported. I’ve had that happen. I’m not a business coach and a lot of people who end up working with me decide they want to start a business. All right. Once you make that decision, it is time for you to go talk to someone else. And so when you are working with anyone to support you in solving these problems, whether it’s a career coach and this is true for therapists as well, tell them if they are not meeting your needs the way that you want them met. 


Anne Helen Petersen: I also think that maybe what this question asker is looking for there might be looking for a headhunter like to be connected with a headhunter in some sort of way. Do you sense that at all? 


Phoebe Gavin: If they went to a headhunter with this question, that person would be able to to. To some extent answer. What kinds of jobs? What kinds of industries? What kinds of money? But the headhunter isn’t going to be able to help you pivot. 


Anne Helen Petersen: Yeah. 


Phoebe Gavin: Their role is filling positions, and what they are going to want is to receive a nice resume from you, put it into their database so they can match you with the roles from the companies that have retained them to fill positions. They are not career coaches. They are not in the business of helping candidates outside of making it as easy as possible for good candidates to get matched with the roles they’ve been paid to fill. 




Anne Helen Petersen: We’ve got one last question about pivoting and how to frame it. This is from Gia, and our colleague Julia is going to read it. 


Gia: All of my jobs for the past six years have been under two years for various reasons, layoffs, moving from part time to full time contracts, etc., including my current role. Is job hopping still the black mark on your resume that it’s been made out to be? I’m looking to change jobs and industries so that my work is more aligned with my education. How do I explain or present my job history in my resume slash cover letter? 


Anne Helen Petersen: Okay, this is a big one because I think that there’s a sentiment and sometimes we do this on the podcast, too, that’s like, if you’re miserable in a job, try to leave it. But also, there is wisdom in staying at a job that is not perfect in order to get enough experience and enough time under your belt that it doesn’t look like you are the person who leaves under any duress or like can’t find satisfaction in a job. What is your thinking on this, Phoebe? 


Phoebe Gavin: If you would have asked me this question in 2019, I would be giving you a very different answer. But the last three years have just been so crazy, and reasonable recruiters and hiring managers know that there are a lot of really great people out there who have a choppy 2020, 2021, 2022 situation and that no fault of their own and they are more willing to entertain the idea that that choppiness is not a reflection of the quality of the candidate, but a reflection of the economy that we have experienced over the last four years. 


Anne Helen Petersen: Yeah. 


Phoebe Gavin: So the thing that that sticks out to me about this questioner is that she’s saying that this is a six year period. So we’re going back before pandemic times and we’re still having some choppiness. And I think that depending that’s kind of a different story. If I was working with this person, I kind of would have to give them some bad news. You know, depending on the details, we can do some resume magic. The cover letter can do some heavy lifting in terms of sort of smoothing over the rough edges and creating a narrative that makes sense to a recruiter or hiring manager who doesn’t know you, who doesn’t know your capabilities and wouldn’t be able to apply COVID compassion to the professional experience that was choppier prior to 2020. And so that kind of brings me to the next key thing. When you have sort of a challenging narrative, a challenging timeline is that it is absolutely essential to network. People are more skeptical of strangers and they are more trusting of people they know. And so if you want less skepticism and more trust, then you need to beef up your network. And so putting effort into getting more involved with professional associations, doing some, you know, LinkedIn research to try to find the kinds of people who are doing the kind of work that you’d like to transition into, the kinds of people who work at the companies that you’d be interested in and becoming building your proximity to the opportunities that you would like to have, that is going to increase the likelihood that the recruiters and hiring managers who you interact with your applications are going to be warm or lukewarm versus cold because those cold recruiters and those cold hiring managers are going to go through the pandemic years and say, oh, you know, man, it’s too bad it was a really sucky few years and then get to that previous time and then it becomes a real question mark. Now, job hopping doesn’t really have an official definition. I say 18 months. There are people who say two years. I think the problem is more that it’s consecutive. Once you get into this next role, try to really be thoughtful and intentional about choosing it so that it has the highest likelihood of being one where you can stay for more than 18 months, two years, ideally three years, because then it’s like we broken the chain, stuff happened, and then I found this really great job. I stayed in it for three years. I learned of it. I drove some results. I improved upon those results and now I’m ready for the next opportunity. That is a narrative that most recruiters and hiring managers are going to be able to get around. But if we continue having the choppiness, it just kind of gets harder over time. 


Anne Helen Petersen: Can you say just explicitly what job managers and hiring managers like? What do they what is it? What are the messages in their head when they see that choppiness in a resume? 


Phoebe Gavin: So most people who don’t have hiring experience or have never run a business don’t realize that payroll is the most expensive, is the biggest line item in a company’s budget. It doesn’t matter how big or small the company is. Payroll is the biggest line item. People are very, very expensive. Hiring people is expensive, training people is expensive. Managing people’s performance is expensive. Firing people is expensive. Believe it or not, laying people off is expensive—


Anne Helen Petersen: Super expensive. 


Phoebe Gavin: Everything associated with people. Everything associated with people is expensive. And so any time you’re going to make a hiring decision, all of that is weighing on you that like I need to get this right because if I don’t, it’s going to be really expensive. And it’s not just expensive in terms of spending the money to accomplish those tasks, but also losing the results that you would have driven if you had the right person in the job doing the role well, fully trained, operating at their optimum level. And so when they see when recruiters and hiring managers see a choppy resume, they are wondering why, why, why might that be the case? Is in a pre 2019 logic chain for that could be well, you know, maybe they aren’t a very good performer. Maybe they aren’t very dedicated to the work that they’re doing. Maybe they’re impossible to please. Maybe they jump every time they see a new job title or a new compensation level. And don’t get me wrong, those are all perfectly reasonable reasons to leave a position. But again, we’re occupying the mindset of a recruiter or a hiring manager who’s thinking about all of these costs to the organization. If they don’t get this role right, if they don’t pick the right person. And so they are being a little bit more conservative about how can we make sure that we choose the right person. And they’re looking actively looking for those red flags. And once they get to the point where you’re having a conversation, you can talk through your narrative and you can help them understand the full context. And ideally, your cover letter does a lot of this work as well, and that can assuage some of the concerns that they might have around the choppiness. 


Anne Helen Petersen: So I think our advice to this person would be that they can start doing that groundwork of looking to change jobs and industries right now. Perfect time to start doing that early work, but maybe try to get to that two year mark in order to show a shift. 


Phoebe Gavin: Yeah. Another thing too, a piece of context that we don’t have about this person is where they are in their career. 


Anne Helen Petersen: Yeah. 


Phoebe Gavin: If you’re early in your career and this is sort of been what the situation is, you probably can get a bit more compassion. I graduated in 2018 and you know, my first couple of jobs, I was figuring it out and then I landed in a really great place and then they laid everyone off due to the pandemic. And then this happened and then this happened. I really just want to find a place where I can settle in and do my very best work. I’ve assembled a lot of skills and experience over the last six years, even though it’s been at a few different companies, and I’m looking forward to putting all of that together to drive the results necessary in this role. That’s a great thing to say, but once you become more mid in your career senior in your career, that narrative doesn’t exactly work and you kind of have to go about it a different way. 


Anne Helen Petersen: I think this is a fantastic place for us to wrap up. Phoebe, this has been such a pleasure. I feel like I don’t have any jobs to search for, but I feel like I would have the encouragement to go like start journaling and figure out what kind of job I’m looking for. If people want to find more about you on the Internet, where can they look? 


Phoebe Gavin: I am on your favorite social media platform @BetterWithPhoebe and you can go to To sign up for my newsletter and attend my free workshops. 


Anne Helen Petersen: Amazing. Thank you so much. 


Phoebe Gavin: Thank you. 


Anne Helen Petersen: Before we go, a hot tip about keeping up with the news. For a quick and punchy take on the state of our world and how much longer it can hang on. Look no further than Crooked Media’s What a Day newsletter. In just a few minutes, you’ll be up to speed on the day’s top news story, as well as stories that may have gone under your radar. Subscribe to the What a Day newsletter at Thanks so much for listening to Work Appropriate. We are working on a bunch of exciting episodes right now and we need your questions. We’ve got one on all things pregnancy and work, one about creating a healthy and enjoyable remote culture and one on creating boundaries between work and the rest of your life. If any of these sound like something you’re going through, head to to tell us your quandaries. That link works best on desktop, so if you’re using your phone, you can also just email us at Don’t forget to follow us at Crooked Media on Instagram and Twitter for more original content hosts, takeovers and other community events. You can also follow me on Instagram @AnneHelenPetersen or you can sign up for my newsletter Culture Study 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]