Navigating Freelance Career Transitions with Simone Stolzoff

SEASON 7, EPISODE 3

Navigating crossroads in our careers isn’t easy — not when we’re traditionally employed, and certainly not as freelancers, where we pick the rules. The possibilities can seem endless. One assignment, one client, or maybe even one email can completely change what we decide to do next. While considering making a big career shift, we can sometimes feel stuck, and the next steps might not feel immediately obvious.

In this episode, guest host Simone Stolzoff joins Wudan to talk about how to navigate big career transitions.

Simone is a journalist and designer based in San Francisco who’s published in The Atlantic, New York Times, and many other national outlets. He’s also an expert on work and teaches a whole class on designing your next career step. His first book, The Good Enough Job is out on May 23. He has had a fascinating career, weaving from journalism to working at the international design consulting firm, IDEO, and back to media. You can follow Simone on Twitter here.

Simone outlines steps to take while considering making a big transition and drops some tips so you can go from idea to action!

Full Transcript Below:

Wudan Yan- Hi, everyone! Welcome back to the Writers' Co-op, an anti-hustle business podcast for freelance creatives. This is Wudan Yan. I am your host and executive producer. How many of you listening feel like you've reached points in your freelance journey where you wanted to throw caution to the wind and change direction? Whether that's "maybe I should quit journalism entirely and make more money doing content marketing," or "let me hire out a bunch of subcontractors and grow my business?" Or even "wow, freelancing is super exhausting. Maybe I should just get a full-time job with paid vacation and benefits?" Or like, "should I just go back to school and get a PhD?" Or "should I start a podcast?" It can even be more subtle, like an interesting opportunity comes through your inbox, and it's not what you're doing now, but you are intrigued. Let me say that navigating these crossroads in our careers is not easy. Not when we are traditionally employed, and certainly not as freelancers, when we pick the roles and where the possibilities feel endless. Last season on the show, we talked about inflection points—slight adjustments that you might want to make when you are at a moment of potential change. We will link to it in the show notes, because it's a pretty good episode. But I'm talking about these bigger swings. Because after those questions, thoughts, and the realization that there could be something new, something different, what happens next? Usually, it's followed by paralysis, like "wow, I've never done that before." And the next steps don't feel clear in that moment. I experienced and worked around this when I was about nine months into a PhD program and realized that, like, it was not for me. I wasn't excited by reading journal articles or sitting in lectures or pipetting. My doctoral program would have been in translational medicine in cancer biology. So, yes, there was a lot of pipetting. What I was excited about, at the time, was spending my time commuting around New York City with some physical copy of a magazine tucked in my purse. I voraciously read narrative nonfiction books. I was also really excited about my yoga practice. And around that time, I went to a talk at the World Science Festival in New York City, where a few science writers were talking about their books. It dawned on me then that science writing was an actual career path, not just something people could do on the side, because their primary career—whatever it was, research, academia—allowed for it. But even in that moment, I wasn't sure how to get from like, point negative 25 of me being in grad school to point B, which is being a science writer. We were not even on the same numerical or alphabetical scale. So instead of having this next step live in my head, I started telling people. I will admit, this was really scary. Because for me, once I start telling people something that I'm thinking about, it opens those individuals up to holding me accountable. Like if I follow through, amazing. But if I don't, I'd have to deal with their questions of "oh, but what happened next?" I told people outside of my program, who wouldn't judge me for wanting to quit something that had literally just started. And I will say that something incredible began to happen. They told me about people they knew who were working in science communications in media, and offered to connect me with them. Those conversations were invaluable. And now this is the first thing I recommend people to do if they're thinking about anything new in their careers, which is talk to other people already doing the thing. From those conversations, I was encouraged to try a few things. First things first, I was advised to make sure I actually enjoyed writing. This feels like a no brainer, but I was about to start doing something very different. And it would be good to make sure that I would actually enjoy the very act of writing and typing into a blank Word document frequently. So I started a blog where I just practice writing about new scientific findings. I am not sure if anyone ever read it. I did not need anyone to. It really was just for me. And then I talked to other people who gave me options on what I could do next. Just try some editorial work, they said. Like any kind—fact checking, copy editing, maybe even research. And that approach worked as well. So in addition to the advice of: Do something else to support yourself in the beginning, financially. And when I was finally able to envision that near future of cobbling a few things together, I finally did the scary thing and quit my PhD program. What I did then, without knowing it, was designing these next steps of my career. Like, not diving immediately into the deep end, but coming up with discrete steps that felt way less daunting. This week on the show, I asked Simone Stolzoff to come on to talk about designing your next career step because, this is literally a thing he teach. Full disclosure, Simone is a colleague. He's also a friend. So throughout the course of our chat, you'll catch me calling him Simo instead of Simone because that's how I know him. Simone is a journalist and designer based in San Francisco, who's published in The Atlantic, New York Times and many other national outlets. He is an expert on work. His first book, The Good Enough Job is out this month on May 23. And he's had a fascinating career weaving from journalism to working at the international design consulting firm, IDEO, and back to media. I am really excited for him to share his wisdom on how to go from an idea and paralysis to action. Hi, Simo. Thanks so much for coming on the Writers' Co-op. It's a pleasure to have you here.

Simone Stolzoff- Thanks so much for having me.

Wudan- I'm really excited to talk about career pivots, career transitions with you. But first, I wanted to hear a little bit about your career journey and what brought you to freelancing.

Simone- Yeah, I've had a meandering path, so to speak. I've worked in many different industries. I worked in tech and design and in food and in journalism. In college, I studied poetry and economics, which probably set me up for a life of inner turmoil. There's always kind of been this tension between art and commerce in my life. And so when I worked in industries other than journalism, other than within the newsroom, I always freelanced as a journalist. And now I am completely freelancing and working for myself in anticipation of my debut book that's about to come out as well as doing some freelance magazine writing on the side.

Wudan- Was it a big career transition for you to go fully freelance? What was that like?

Simone-Yeah, I mean, although I have worked in all these different industries, I had never worked for myself as like my primary means of making rent. And I've learned a lot about it in the process. You know, the one of the great ironies of the book is that, you know, I was writing this book about the culture of work in America. And for the majority of it, I was doing it on the side of a full-time job, you know. So I was having to try and practice a lot of what I preached in terms of setting boundaries and making sure that work did not completely subsume my life. And then at the end of the journey, about a year ago, I decided to make the leap and try my own—kind of hanging my own shingle and trying to make it as a freelancer. And I've learned so much about myself. I think that's probably a common trait among people that have tried this freelancing journey, is it can be a great source of growth and a great source of self-discovery, as you learn who you are when there aren't an employer or a manager or coworkers shielding you from some of your innermost emotions.

Wudan- Yeah, I know that well. And I think too, one goal I have for this episode is for listeners to come out with a sense of how to navigate their own career transitions. So I'm just curious if you can talk a little bit more about clues that were coming up in your own life that a transition to freelancing was about to happen.

Simone- Yeah, I've heard it framed before as sort of "the pebble in your shoe." You know, and maybe that's a relatable experience to others who have maybe been in a job and something didn't quite feel right. Or maybe you've been in a job, but had this sort of itch to try something different. You know, I've had sort of four big pivots in my career, thus far, and they've all been spurred by different catalysts. But I think the most recent one was just this idea that I wanted to be able to be giving my best energy and my best hours in the day towards the work that I felt was most important in my life, which for me, in this past year, has been working on this book. The book is called The Good Enough Job, reclaiming life from work. And in it, I sort of make the argument about the value of diversifying your identity, about who you are beyond just what you do professionally. And so the other side of that coin is making sure that I also had time and energy in my life to be able to invest in other sources of meaning: my relationships, my local community, my health, other realms of my life that often got crowded out when I was spending too much time working. And so I think that was really the first sort of clue of knowing that, okay, I am working a full time job. I'm trying to write this book on the side. And yet, I want to be able to be living in a way that feels more congruent with my values, so that I have time to be able to invest in the things that matter. And so far, that's been borne out. You know, I've been freelancing for about eight months now full time. And it's really empowering to have more control over my time and my schedule.

Wudan- I love that and you did the host's job, my job, of introducing your book, which is amazing, because that dovetails perfectly into the next question that I wanted to talk to you about, which is: Your book is all about reclaiming life from work and so how do you put career transitions in the context of that and the rest of our lives? And what does it mean also for a job to be good enough? It doesn't seem like a nod to quiet quitting.

Simone- Yeah, I mean, there's sort of two origins of the title. So first is the good enough job relative to the dream job. It's sort of a foil to the dream job. I think you and I are both are sort of smack dab in the middle of the millennial generation. And I, at least, was raised under certain scripts around, you know, basically follow your passion, you can do what you love for work, you should keep looking for a vocational soulmate, and never stop until you find it. And I think on the other side of 30, I developed more appreciation for a job as being part of but not the entirety of my life. And the second is an allusion to this theory developed by this social scientist and pediatrician and psychologist named Donald Winnicott. And Winnicott was a British man and kind of the mid-20th century, and he came up with this idea of good enough parenting or more specifically, the good enough mother. And what Winnicott was observing was that there was this growing sort of idealization of parenting. Specifically in the UK, there were so many parents that wanted to shield their kids from experiencing any negative emotion. And then when their kid inevitably felt fear, or anger, or frustration, the parents took it extremely personally. And Winnicott advised that instead of valuing perfection as sort of the ideal, both the kid and the parent would be better off if they valued sufficiency, to think about what it would mean to be good enough—because then the kid could learn how to self-soothe, and then the parent didn't get lost in their children's emotions. And so in the book, it's sort of a parallel to the working world today. And I, along with many others, have been observing this like growing idolization of work, of our professional lives, our dream jobs, looking for work to be perfect. But, you know, much like a screaming toddler, our jobs and not always something that is in our control. And so I'm making sort of a similar argument about what would it mean for a job to be sufficient, as opposed to perfect? And then in the context of career transitions, I think, you know, when we think about career pivots, or career transitions, we often think about it through just a professional context. What would this new career path, or what would this new job, allow for me in terms of money, or title, or status, or prestige. But I think one of the most empowering aspects of a career pivot or career transition, is you can really think about work holistically in the context of the rest of your life. You can think about, okay, what are the elements of my life that I want to be able to focus on or optimize, and maybe in this new transition, I'm not actually optimizing for the highest salary or the most prestigious title, but in fact, a job that lets me get off at a certain hour to pick up my kids from daycare. Or a job that doesn't exhaust me so that I can't do anything else over the course of the day. So when I think about career transitions, I think about them in the context of greater life transitions, and how a change in work can be a catalyst to a change in lifestyle as well.

Wudan- There's also an identity component to this too. And as you correctly stated, we are both smack dab in the middle of millennials. But I think, too, so many people around this age cohort have internalized that we are what we do, and I think career transitions kind of shake that up, right? Like, whatever you did for the last X number of years, it might no longer be a true component, a central part of your identity, if your identity is so closely tied to your work.

Simone- Totally, yeah. And I think this is a uniquely American phenomenon. You know, we all know the sort of canonical small talk question of what do you do? But you know, in today's age, social media, we just parade our professional identities around for the world to see. And I think, you know, the pandemic in particular has catalyzed a little bit of a push back against that, and helping people think about how they identify beyond just sort of their job title. And so I think there's sort of two sides to this. On one hand, it can be really existentially angsty to leave a previous job that was very legible to others, that might have been core to who you were, that was reinforced by the community of coworkers that you have. And I think that's one thing I hear a lot in people that are in states of transition is they sort of lose their old identity that they once had through their work. But I think the other side of that is the empowerment that can come from choosing who you are both outside of the office and in this next phase of your career. I think this was particularly on display for the pandemic, where so many people lost their jobs, or at least their jobs as they were, either due to furloughs or layoffs, or just the nature of work changing for so many people. And they were forced to reckon with, you know, who were they without their work. In the course of the book, the people that I interviewed who had the healthiest relationships with their jobs all had a keen sense of who they were when they weren't working.

Wudan- I love that. I think you got something on the nose over there about like those transitions kind of feeling angsty. And I think that's why I really wanted to dedicate a whole episode about how to navigate these transitions. This is something that you literally teach. But before we dive in, I want to talk about this concept that you introduced in that course of design thinking. But what is it? Where does the idea originate from? And how can it be applied to exploring different careers?

Simone- Yeah, so you know, design thinking is jargony phrase, and it can mean different things in different contexts. I spent four years working at this design firm called IDEO that really popularized the idea of corporate design thinking. But when I think about what it means, in simplest terms, it's just a way either individuals or companies going from states of ambiguity to states of more clarity. There's a diagram of the sort of five-step process that you might have seen going from empathizing to synthesizing and researching and prototyping and testing. But when it comes down to it, at the end of the day, design thinking is just a way of learning through experimentation, and empathizing with what different end states might mean for you or for your company. So when it comes to career transitions, and thinking about how to figure out what it is that you actually want, the process can be applied in different ways. Of starting with kind of empathizing with, what are the things that matter to you and how might they show up in these different career paths? And then, instead of necessarily having to take a big leap right away, what are ways that you can design little experiments to see whether what you thought you might want is actually what you do want? So for example, you and I are both journalists. I'm sure a lot of people, especially people earlier in their careers, might come up to you and ask, you know, I really want to be a journalist. What should I do? And for me, often, the first thing I say is, you know, what makes you think you want to be a journalist? And like, have you actually tried to write something before? It's maybe a little simplistic, but there are many ways to test out different career paths without necessarily quitting your job and trying to find a job right away. So for example, if you're interested in doing more writing, maybe you can start trying to write a newsletter, or post on a blogging platform, or try and pitch an editor and get your first piece published. There are these little steps that you can take that might actually help you figure out the lived experience of what it means to be a writer or journalist, without having to necessarily quit your job or go to journalism school or try to, you know, knock on the door of a bunch of different newsrooms until they let you in.

Wudan- Yeah, definitely. And, you know, when I decided to become a writer, a freelance writer, I did exactly that. I started a blog. But I want to back up actually one step and talk about where you think somebody should start if they're considering making a career change, but don't yet know what they want to do. This is like, oh, I have a pebble in my shoe. But like, what is that pebble and like, where should I toss that pebble? Down which alley? How can somebody begin to narrow down their options?

Simone- Yeah, I think it boils down to figuring out what you value and what you care about. I think values are really the foundation upon which all life changes or life transitions are built, this sort of invisible force that motivates us, that influences our behavior. And, you know, I think there are many ways to figure out what you value or what you care about. Some popular ones are journaling or card sorts. Or for me, like, I often think about it from a narrative perspective. And just thinking about times in your career where you have felt most fulfilled. And then trying to really put yourself in that place and break down okay, what about this felt fulfilling? Was it the people I was working with? Was it the type of problems that I was working on? Was it the other aspects of my life that felt like they were in balance around my job? And before you think about any specific job, or any specific career, really distilling those values is a great way to figure out what you yourself care about. Because it's so easy to be swayed by what other people care about, what other people find prestigious. Uou know, think, especially if you're like me, one of the first things that I often do when I'm trying to make a decision is try and just talk to everyone about it. But I think other people's advice tends to justify their own past choices. You know, there's this writer and investor, Paul Graham, and he has this great quote about prestige. And he says prestige warps even your beliefs about what you enjoy. It causes you to work, not on what you like, but what you'd like to like. I think that is so common in the world of like career transitions, is we think about, okay, what would be perceived as cool, what would earn the love of my parents, what would be something that's fun to talk about at the bar with my friends? But all of these are sort of these extrinsically-motivated desires, as opposed to really getting clear on what you care about and value yourself.

Wudan- And social media and living in an era where social media is constant makes that even harder, I think.

Simone- Totally. Yeah, I think it's so easy to see everyone else's sort of professional accomplishments, and we parade them around. And if you go on LinkedIn, or on Twitter, it just seems like this ticker tape of other people sharing their promotions, and their big projects that have launched. And that noise can really be distracting to our own intuition and our own sense of okay, that might be great for them. But what is actually right for me?

Wudan- Simo, can you actually share like, personally, what you value from what society tells you to value?

Simone- Yeah, totally. I think, you know, the process that helped me the most was this card sort activity that I did. It's something that's very common like kind of the therapy world. And there are many different card sorts that make you go through your values. But the general idea is, there's this deck that maybe we can link to in the show notes—

Wudan- Yeah

Simone- —that has like 100 different values. So community and creativity, and prestige, and love and passion, and all of these different sort of one word phrases of these different values that you could potentially hold. And the idea with the card sort is you just kind of go through them all quickly, and try and make different piles of what you really care about, what you somewhat care about, what you don't really care about, and what you definitely don't care about. And then within the pile of the things that you really care about, you'd have to boil it down to 10, and then three as sort of like the forcing function. I think the key there is like thinking about values relative to one another. You know, like, no one in the world probably doesn't value family, or doesn't value friendship, but thinking about your unique composition, it can show you that, oh, maybe what I care about is stability and security a little bit more than than novelty and excitement. Or maybe it will show you that oh, what you care about is, you know, making money or what you care about is having creativity in everything that you do. And just having that language and that, that visibility into what it is that you care about can really help make any decisions from there.

Wudan- This card sort seems like a gamified version of like the values wheel that I know is pretty prevalent in business leadership circles, right? Yeah, this came up in an episode this season about success, and how we can come up with our own definitions of success too, based on our values. So check that episode out if you haven't already.

Simone- Yeah, I think there's a real parallel to the corporate world. And you know, I think like corporate values get a lot of shade, sometimes rightfully so, because they can be vague and not really mean anything. But ideally, if you have very clear corporate values, that can be something that you can fall back on in any sort of decision point or fork in the road that you're going through.

Wudan- That makes total sense. So Simo, let's get a little bit tactical and talk about what research somebody could do when considering different careers. Like what is that research process like?

Simone- Yeah, so, I think we're all familiar with the sort of informational interview or just asking people about what they do for work and whether they like it or not. And I think that can be one great method to research and figure out what you actually care about, but what I'm always pushing people to do a bit more of, is to have that experience be a little bit more embodied. So say you are considering whether you want to go back to medical school. As opposed to just interviewing, you know, doctors or interviewing nurse practitioners or nurses about their experience, is there a way that you can actually go and shadow someone, and feel what it's like to feel yourself in the context of a hospital environment every day with all sorts of coworkers? There's this sort of example that I think about a lot from my days working as a design researcher at IDEO. And what happened was, we were trying to design a better vacuum cleaner. We were working for Dyson. And so we went into people's houses, and our sort of like rough prototype was a broomstick that was taped to a tissue box. And we would give that sort of very rough prototype to a bunch of folks and say, "okay, would you pretend that this is a vacuum for us, just humorous, and like, show us how you would use it around the house?" And, you know, there's, I think two benefits. One is, as opposed to spending hours and hours and hours, like in our studio trying to come up with this really polished final design, we had this very low fidelity prototype that we could put into the field and learn as quickly as possible. And then second, after this sort of experiment was run, I remember hearing about one of the researchers that asked one of the participants and said, "so you know, what did it feel like when we handed you this broomstick and said, you know, pretend it's a vacuum?" And the interview subjects said, "I felt like you guys could really use my help." And that's like, just a very common experience of just even the lower fidelity the prototype, the quicker you're able to learn. And so similar to the product development lifecycle, getting into the field, putting things into people's hands, the quicker, and the closer proximity you can have to the actual path or job that you're exploring, the better. As opposed to treating everything like a thought experiment and being like, "oh, I suppose I might run for Congress. But would that really be the fullest expression of my unique identity and personality?" Like, go out and try it and see if it actually lives up to your expectations of what you thought it might be.

Wudan- You're talking about these informational emails. Have you sent them yourself? And usually, like, how do you approach them? Because I feel like I get them all the time. The can I pick your brain sort of situation? And I inherently hate that phrase, but also, I don't have that many hours that I would like, for somebody, to really peep into my day.

Simone- Totally. Yeah, I think there's a few things that stand out from good cold emails and bad cold emails. Our mutual friend, Anne Helen Petersen, actually has this great essay that she just put out on the difference between a good and a bad cold email. I think it starts with showing that you've really done your research. No one wants to have to rehash things that can be easily found on Google. And I think from my perspective, I am so much more inclined to respond to a request for information or a question or an interview if it feels like I can be helpful in a really tangible way. And so the more specific the ask, and the more tailored to something that I can uniquely answer, the more likely I am to engage. I think the biggest pitfalls that I see from people in sort of cold emails or cold outreach is one, they make it way too long. You know, just from a formatting perspective, if I see a five paragraph email that's going so, so deep into all of these different facets of people's lives, from a stranger, it takes a lot of both like emotional and mental labor in order to just parse out okay, what are they actually asking? So keep it short. The second is have some flick at the fact that you've done your research on who I am and what I what I care about. I always love this sort of like wink or the nod to showing that you've engaged with my work in the past or that you've taken the time to determine that I am actually someone that can help you for this particular reason. And lastly, try to make it as easy as possible for me or whoever you're reaching out to, to say yes. So for example, I'm about to go on a book tour. And I'm going to be in all of these different cities. If you are hoping to speak to me, and you can make it as easy for me to say yes as possible, the more likely I am to do so. So if you say, "okay, I'm going to come to your event in Seattle, that you're doing at Elliott Bay with Wudan. And would you mind sticking around for five minutes afterwards to help answer this question I have for my grad school application?" or "I saw that you're going to be in New York on this date, and there's a coffee shop that is going to be very close to where I know you're going to be, can you spare 20 or 30 minutes to chat?" Those sorts of pre-work aspects that you can do to make it easier for someone else to say yes can really be the difference between getting someone who's very busy's time and just going into a kind of a slush pile of emails.

Wudan- Yes. I love all these points of advice. And I think this episode is going to come out in time. So if folks are in Seattle on May 30. It's 7? 7:30pm? I don't know. In the evening at Elliott Bay, come and listen to us talk about Simo's new book, but that is a tangent. So we're talking about the steps in progression, right? Like see what it's like what these other jobs are like. And my next question is, how do you test out these possible options before taking your next step. And I mean this specifically in a freelance context, because I think freelancers can fit like one small experiment in into the rest of what they're doing in a way that I feel like a lot of people working full time might not be able to

Simone- Yeah, I think there is a natural inclination to want to take big leaps. Those are the stories that are often celebrated and championed in the world of career pivots, or career transitions, where, you know, "I used to be an elementary school teacher, and now I'm an astronaut," or "I used to do this and now I do that." But I think the path from one line of work to another often goes through a liminal period, or a stage that combines some of your unique past experience with your unique future experience. So let's take the example of someone who has been working as an elementary school teacher and recently started freelancing as a journalist. So rather than go for the moon right away and say, "okay, I spent, you know, seven years in the classroom. And now I want to write about immigration for The New Yorker." Think about what from your past experience you can parlay into making you a unique or attractive candidate to be hired in this new path that you're going on. So maybe that starts with writing about education and writing about things that you have lived and earned experience from. Maybe it is thinking about the networks that you have from past work experience, and what opportunities are most accessible to you today. That doesn't mean that you shouldn't ultimately be working towards your biggest dreams and, you know, shooting for the moon. But I think it's often hard to make those big leaps without taking some of those intermediary steps. And so when I think about transitioning in the context of freelancing in particular, I think about it less like one big leap, and more like subtle nudges to be doing more and more of the work that you want to be doing. I think for freelancers in particular, I've definitely felt this, there's sort of a seesaw, where on one hand, there's your heart. And on the other hand, there's the dollar sign. And it's this perpetual balance of trying to find where is the place where you can be making enough money to sustain your material existence and doing the right amount of work that aligns with your interests, so it doesn't feel like you're completely selling out? And I think even the most experienced freelancers out there are navigating this wobble. For me at least—so I left my job last summer to finish working on the book. And I took a consulting gig that was copywriting. It was kind of corporate landing page writing for a startup, and it wasn't the sexiest work. It's not the work that I talk about on my website, first and foremost. But having the consistency of a two to three days a week job, that was a consistent paycheck, was what allowed me to take more risks in those other two to three days. of the week when I wasn't working this consulting job. And I think that this is something that rarely gets talked about in the freelance world. Almost every freelancer I know has that anchor gig, has that stable source of income, that allows them to be able to explore other aspects of their work life and allows them to test out these other possible options. So although there's a lot of kind of cachet and taking these big leaps, I think about how can you kind of dot that path with stepping stones?

Wudan- Mmhmm. Yeah, sometimes I take on like very small assignments, like trial assignments to be like, this seems interesting on paper, but what is it like to do the thing? And because usually, these are one offs, I can, you know, say no to future work if the assignment is complete and I do not feel like it aligns with my values at a particular moment. Or I shelve it and revisit it later.

Simone- Yeah, that makes a lot of sense. And it can be a mutual fit. You know, I think, especially when you're just starting out in freelancing, there can be an inclination that you should be taking every single gig that comes your way. And slowly, with more experience and more clarity in terms of what you want, you can afford to be a little bit more choosy about those roles. But I think often when you're working for yourself, or when you're freelancing, it's easy to kind of discount your own value and say, "okay, I'm just gonna take this job because it's being offered to me." But much like a interview for a full time job, it should be a mutual fit. It should be an effort of you trying to determine whether you want to work for this company, in addition to them determining whether they want to work with you

Wudan- Totally. Okay, so after you've gone through the ideation process, the research process, the testing process, what do you do next, after you've decided on the path forward that you want to take in the imminent future?

Simone- Yeah, so, you know, this is a place where it's harder to give prescriptive advice. Because it's, you know, different strokes for different folks. I don't necessarily know what your path forward is. If you're deciding that you want to go to grad school, it might mean, you know, taking certain prerequisite classes. If you're deciding that you want to pursue a career in documentary filmmaking, maybe it means, you know, building your network or trying to work on some projects on spec. And so you can build a portfolio towards that aim. I think more than having decided on a particular path, what I often advise people is to think about your version of your life well lived. Think about the sort of utopian vision of how you want to be living, and then think about how work or this gig or this career fits into the context of that. One of the great benefits of working for yourself, or for freelancing, is you have, ideally, a lot more agency and autonomy over how you want to craft your life. But one of the common pitfalls is that people realize that, "oh, I am actually my own worst micromanager."

Wudan- Yes.

Simone- This scarcity mindset of not knowing when the next gig is gonna come can push a lot of people to overwork, to not respect their boundaries, to let work seep like a gas into all of the unoccupied space in your life. And I think the risk there can be managed by making sure that you're also being intentional about your new life outside of your job or outside of how you're making money. I've seen many freelancers that go into working for themselves with the intention of being able to take a run at 2pm on a Tuesday, and they let the instability or insecurity just crowd out that intention completely. So in addition to thinking about what possible options are before you from a work or a career standpoint, really try and create a life view, a perspective on what you want your freelancing life to be like that can coexist with your work view or your world view of how work fits into it.

Wudan- For sure. And my last question for you is: How do you hold yourself accountable to these like new career paths, these new goals, while still staying flexible for other opportunities that arise? And I guess, as an addendum, I would like to know if you also like intentionally designed that sort of flexibility for newness in your freelance work and business?

Simone- Yeah. Totally. I mean, I think this part is tough. And it comes with developing a comfort with ambiguity, which, especially in the US, and especially if you come from a very sort of go-getter, straight A background, it's really challenging to be like, "I know what I'm going to be doing for the next month, and I don't know what's going to come after that." I think the key is to cultivate a sense of faith. I don't necessarily mean this in like a religious or spiritual context. I mean this more in faith in yourself and faith in your worth, and faith in your ability to figure things out. So for example, right now, you know, I have a book that's coming out this month, and I know that I have a certain amount of work that I'm gonna have to do around the book. But come August, I have no idea what I'm going to be working on. I don't have many leads for clients come that time. But what I'm trying to do is ground myself in the fact that I believe that there's value that I can add to clients or newsrooms or organizations in the future. And I believe in my own ability to cultivate leads, to find those opportunities when they arise. And I've done enough groundwork right now to understand the slack that I have in my budget and in my schedule, in order to afford some wiggle room when it comes to when exactly things are going to come through. I'm not saying that this is easy. Cultivating faith is is often easier said than done. But I think it's a necessary ingredient of this path. And even on the micro scale of knowing that, if it's a Friday afternoon, and you want to honor that you'll be able to get the work done next week, you can close the laptop or close your email, without letting that crisis of faith pushing you to keep working past your own limits and boundaries.

Wudan- I do think, too, that setting the groundwork and the way I see it described by other freelancers is like, always be marketing. And I don't like the term marketing. I'm actually going to record an episode about not using that word anymore. But just like, I think as journalists, both of us are inherently curious about other career paths, other jobs, etc. And I think that builds into my day to day immensely. I'm kind of always looking for opportunities, like even if it's a not now, it could be a later, like maybe in August, when things calmed down a bit. So I feel like that's also something to think about, not just even like marketing yourself, but just talking, like continuing to talk to people as you're doing the work.

Simone- Yeah. And I think especially in the career realm, the decisions we make, and the choices we make are not trapdoors. You know, they're much more reversible. Or we have much more capacity to course correct if we give ourselves credit. And that's something that I would also keep in mind. Even if you're making a change, or you're exploring a different option, you can still likely go back to where you were. I definitely felt this when I was leaving kind of a staff writer position in the newsroom and thinking, "oh, my God, have I tainted myself? Will my former coworkers never respect me? Will they think I sold out?" And the truth is, you know, I think it's called the spotlight effect. Basically, no one cares about you as much as you care about yourself. And you have the ability to course correct if you need.

Wudan- I love that. Careers are quite flexible. Well on that note, I think that's an end to this. Thank you so much, Simo, this was really great. And I kind of wish I had it like a decade ago when I quit grad school. But that's my job now, is creating everything I wish I had 10 years ago.

Simone- Yeah, well, thanks for the work that you do to highlight this. And if anyone wants to think more intentionally about developing a healthy relationship to work, my book is called The Good Enough Job: Reclaiming Life from Work, and it's currently available anywhere books are sold.

Wudan- Thanks so much to Simone for coming on the show. You can follow him on Twitter @SimoneStolzoff. His book, The Good Enough Job, is out. Find it wherever you buy books. And if you want to take his course, I'll link to that in the show notes as well. There are rolling cohorts of classes so you can sign up for his newsletter to stay in touch. Patreon All-Access members will get a worksheet to help you design the next step in your career. If you're not yet a member, join us. In addition to these handy resources that accompany every episode, you will get deep discounts to other TWC events and resources. And the best part, I would say, is that you automatically are invited into our inclusive and safe Slack community for like-minded freelance creatives. I hope to see you there, and talk to you all next month. Thanks so much for listening to the Writers' Co-op. If you've enjoyed our episodes, please rate, review, and subscribe on listening platform of your choice. These reviews help more listeners discover us. You can join us on Patreon at an All-Access member level at patreon.com/TWCpod. This gets you access to discount codes for events, for other objects online and our safe and inclusive online Slack community. The show is hosted by me, Wudan Yan. Our producer is Margaret Osborne and our editor is Susan Valot.