349: Embracing Doubt and Going for “Good-Enough” Work with Simone Stolzoff

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It's not that good enough means lowering your standards for the quality of work that you're producing.

I think.

I think it's an acknowledgement that when we invest in other aspects of who we are, when we're able to diversify our identities, it can create fuller versions of ourselves, but it can also produce better work as well.

What's next? This is a question we're all having to ask and answer more frequently. I'm Jenny Blake, your host of the Pivot podcast and author of Pivot. The only move that matters is your next one.

For show notes from this episode, visit pivotmethod.com podcast. If change is the only constant, then let's get better at it. Here we go.

Welcome back, Pivoters. I am so excited to have Simone Stolzoff here with us today. Simo is an independent journalist and consultant from San Francisco, just coming back from his honeymoon. He's a former design lead at the global innovation firm ideo. He he works regularly with leaders from the Surgeon General of the US to the Chief Talent Officer at Google on how to make the workplace more human centered. His feature writing on the intersection of labor and Silicon Valley has appeared in the Atlantic, Wired, the San Francisco Chronicle, and he also has an article of the Week Book Club Style Substack. And I've seen his new book featured all over the place too, which is super exciting. So that's the topic of today's conversation. His newish book, the Good Enough Reclaiming Life from Work. Simo, welcome to the show.

Thanks for having me on.

Jenny, you took a really unique approach to writing this book in that you interviewed over 100 primarily white collar workers, but the format is that you feature nine stories in depth. I thought that was such a unique creative choice. So I would love to know what inspired you to take that route.

Maybe some business or nonfiction books that you've read. It's not a book of tips and tricks. It's primarily people's stories. And the choice to feature people's stories is a fewfold. One is it's a book about careers and the ways in which we place work in the context of the rest of our lives. And I think many people's careers might look one way on paper, but when you really dig into the nuance of it, it can look very different when you get to see all the twists and turns or irrelevant to pivot listeners. And I think the other reason is just the fact that I love writing. I got into journalism from the writing perspective obviously resonate with the idea of accountability reporting and democracy dies in darkness. But the thing that really lights me up, the thing that I get really excited about is the prose themselves. And so that was the goal, is to really write people's stories and see how as a reader and as a reporter in my case, I could see my own life reflected back in them.

That word reflected. I thought it was inspiring how you said my goal is you'll treat this book less like a textbook and more like a mirror. That is to say, I hope this book prompts you as writing it did for me to examine your own relationship to your job. That was such a wake up call as a reader. It was like you're not just going to sit here and read yet another career book or career change book or self help book for that matter that treat it less like a textbook, more like a mirror. Felt like a real invitation and a call to action for the reader to say look in the mirror of these stories. They all have threads that are probably going to relate to you.

That's definitely the case for me. In the different stories there's a Wall street banker and there's a software engineer at Google and there's a Michelin star Che. These people who you might not necessarily think you have anything in common with. But the benefit of a narrative approach is it shows that the struggles are often common. Regardless of what industry you're on or what phase of your career you're in. There are issues that we're all trying to wrestle with in terms of trying to right size workplace in our lives.

The Wall street banker you mentioned, Kahi, is a friend of the pod. We've done five episodes together that I'll put in the show notes.

Yeah.

So I loved reading your in depth story about him in the chapter on status games. And I also appreciated how you say later in the book that it's still a work in progress for you. You say I'd be lying if I told you I'd found an easy way to do so myself. Without realizing it, working on this book has become central to my identity. How has your relationship to even the book, writing it, launching it. Now we're post launch phase. You ended up quitting your job at ido, so that you could be doing this full time. So I'm just curious, now that the book has been out for a bit, has anything surprised you since you wrote that conclusion?

I mean, it's been a big year on a number of different fronts, but one of the things that I think has surprised me the most is that left the corporate world to focus on finishing the book, and now I'm working for myself for the first time.

And.

And maybe, like other pivoters, I have learned kind of the hard way in the ways in which, you know, I thought it was the corporate world or it was my manager, my boss, that was pushing me to work all the time. But in fact, since I've been working for myself, especially in the first few months, I learned that I was the worst manager that I've ever had. It was me and my expectations that were pushing me to work all the time, pushing me to open up the laptop on the weekends. And so I've learned about the difficulties, even when you're working for yourself or even when you have a lot of control or autonomy over how you spend your days, of the ways in which work can kind of seep like a gas into all of our unoccupied spaces. And so, you know, I think the old cliche is that you write the book that you need to read. I think I wrote this book because I was examining the role I wanted work to have in my life. And I don't think even on the other side of three years of reporting this book, it's something that is a fixed answer. You know, I think we'll continue to wrestle with that definition at different phases of our lives. And one of the biggest things that I've taken away is that even people who seem to have it all figured out are often wrestling with their relationship to work still.

Yes. And the relationship to work and identity and money and financial precarity. I found that. I mean, as you just said, every book kind of demands that you live the message. And we wouldn't have the interest in writing the book in the first place if it was something that was coming easily to us in our lives or that we had already figured out. But both with pivot and free time, it's like the joke is always on me. Oh, you wrote a book about navigating change. Great. Here's a pandemic that wipes out all your business for the next two years, or free time even. This year has been really tricky financially, even more so than 2020. And it's like, oh, no, I'm working Twice as hard for half as much. That's not what I wrote a book about. And so I find that even those of us who are aware and trying to decouple our work from our identity or our time life goes in waves and there's different things that happen and. Or your family structure changes or there is no there there. It is not a static thing.

I definitely relate to that. And I think there's the sort of downside of that. You know, we sort of envision this mythical land of work life balance, that once you achieve it, you sort of can float 5ft off the ground in lotus pose. But I actually think there's also a benefit of realizing that it's not a static state that we're seeking because it forces you to wrestle with what relationship you want work to have in your life. You know, certainly this is a question of a certain level of privilege. Even asking the question what do you want to do? Necessitates having some options to be able to choose. But I do think there is a lot to be learned about ourselves when we are forced to wrestle with how many hours, what type of work that we want to do, what type of industry we want to work in. I think one of the biggest messages of the book is trying to urge people to make an active choice. Because if you don't define your relationship to work, as I say in the book, your employer will happily do it for you. You know, it's very easy just to inherit all of the incentives of the company you work for or the messages of the capitalist hustle prone world that we live in. And so if anything, the book is sort of a stake in the ground of helping urge people to choose what they want that relationship to be.

You advocate for. The book is titled the Good Enough Job and you're advocating for just pulling back from this brink of total enmeshment and merging of our identity with our jobs. Where I find this tricky is with creative projects and you again, having just come through the book journey. I want to give it everything I have. Like, I don't want to put out a good enough book. I don't even want to run a good enough business. So as you said, sometimes the challenges when we do have full autonomy, and I'm not even gonna say control when we have the illusion of autonomy and freedom. I just find that sometimes that self imposed work ethic or burnout is coming from a desire to do the best that I possibly can. And so I'm just curious how you're reconciling the Idea of good enough with the pursuits that your name is attached to that you do care deeply about. Question.

And something that I've thought a lot about, you know, even just looking at the title of the book, the Good Enough Job, you might think it's this like slacker manifesto. It's just like excuse to phone it in or spend more time sitting on our proverbial couches. But I think what I like about the framework is that it's subjective, which is to say that you get to choose what good enough means to you. I don't think it's about producing lower quality work. I don't think it's about even necessarily caring less about your job. I think more than anything, my conception of good enough is reconciling the idea that work is part of, but not the entirety of who we are. And so when you are working on a creative project or something like a book where your name is attached to it, I think it's really important to understand that you can still have high standards for excellence. You get to decide what good enough means to you. And in fact, living a life that is of balance, where you're investing in other parts of who you are when you're not burning the candle at both ends to get the project done, can be in service of producing higher quality work as well. And you know, we're seeing this born out on the individual level and thinking about how rest and work are not opposites, but they are integrated in the way that we're able to be sustainably productive over the long term. We're seeing this in the business and the corporate world with some of these four day work week experiments and different ways of working. It's not that good enough means lowering your standards for the quality of work that you're producing. I think it's an acknowledgement that when we invest in other aspects of who we are, when we're able to diversify our identities, it can create fuller versions of ourselves, but it can also produce better work as well.

That reminds me of two things. Something Kay and I talked about for his show Rad Friends is should we play status games? Some would argue we are all playing status games just of a certain variety, but that within the work itself we can define good enough. And then within what the work as a means to whatever end, we can also define good enough. And so what you were just saying reminds me of maybe in our status seeking behavior we can define good enough. Like the good enough car, the good enough house, the good enough wardrobe, things that aren't going to enhance our lives all that much and stop chasing the shiny unconsciously at least. And then as you were talking. Also reminds me, I love your emphasis on individual choice. It's like you can go flat out for a book, but for me, with this podcast, each episode is pretty much good enough. I just get each episode over the hump of what I declare to be good enough. And I know that none of them are perfect. None of the show notes are perfect. The episode itself isn't perfect. I don't even know if people expect perfection, but I have to continuously drop the perfectionism for myself to hit publish. And I know you too, because you've been publishing online for a very long time.

I think that's a lesson that all creators of different realms learn at some point that published is better than perfect. And often when we have these expectations for perfection, whether it's the dream job or being the perfect parent, all they do is they set us up for disappointment. When we have these unrealistic expectations about what a job can deliver, it creates a lot of room underneath that expectation for disappointment or unhappiness.

We'll be right back just after this.

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Even after having written the book. You gave your notice at IDO after four years there, and you said that even still you had pangs of doubt when you gave your notice. So I'm wondering if you can zoom us into that moment, because a lot of people come to me often when they're on the cusp of leaving a fancy, shiny corporate job just because I've been so out there with my story and I'm wondering if you can just zoom us in to was it hard to make that decision? And then those pangs that you felt where you said the pangs of doubt that rushed in afterward, just kind of how you managed that process.

I think this is fairly common for modern knowledge workers, whether it's in the work realm. It can also be true in the sort of relationship or dating realm is something that I've heard you say before, which is that with every choice, with every commitment comes loss. And I think it's important to acknowledge that, that there can still be grief, even if you're making a decision that ultimately might be a better path for you in the future. I left this job at ideo, which was a great job. You know, I had really dear friends that I worked alongside. It was engaging, interesting work. It was in many ways a good enough job. It was a job that allowed me to be the person that I wanted to be in the world. That gave me enough space in my weeks and my days in order to focus on other creative projects like the book and leaving that was hard. And I think often on the Internet we really romanticize people who have made these big leaps and have quit their corporate job to become a painter, to go back to school or to move to Barcelona. And there isn't as much conversation about the difficulty and leaving some of the stability, the security, the friends, the people, the comfort that we have on the paths that we were on. And so it was the best decision for me. It allowed me to write the book and to be able start this new chapter of being self employed. And I don't want to sugarcoat it too much, you know, especially in the first few weeks, the first two months of leaving something that was good, maybe this is relatable to your path as well. I was doubting myself and saying, you know, what am I doing? Why did I leave this job that I've given me so much? But it's really hard to compare unknown, which is, you know, the path that you were on with the unknown of the future. And that's something that I have tried to keep in mind.

So at the time of this recording, how long has it been since you left the job?

Almost my one year anniversary, I think. I left in August of 2022. And then we're recording this in, I guess it's August now, it's the beginning of August and so, wow, one year into this pathless path and so far so good. But I also don't want to discount the idea that I might go back. Is this false notion sometimes when we make big career decisions that they're irreversible or that once you walk through the one way door out the corporate world that you'll never be let back in. And who knows? I'm trying to develop some comfort with uncertainty, ambiguity. And right now I like the path that I'm on. But who knows what I'll want or what I'll need or what the universe will provide moving forward.

One of the questions people ask me the most probably in the last decade plus is do you ever regret leaving? I don't know if anyone has asked you this at any point. After the initial rush of emotion, have you had feelings of regret?

Yeah, I mean it's interesting. I just started working on my next book project and it's about this, it's about doubt and doubt as an emotion, doubt as an experience and sort of the ways in which doubt can be. A teacher and I have had lots of doubt. You know, maybe it's just sort of the neurotic Jew inside of me that naturally likes to play my own devil's advocate or doubt myself. And yeah, I have felt feelings of regret or there have been moments where I'm like, why am I paying hundreds of dollars for health care just to be self employed? Or why am I taking on all the stress of running a business on my own shoulders as opposed to dispersing it over the shoulders of many other people? Am I doing the best thing for my future family? Or can I pay for my kids college if I continue to be an online writer? And the answer is, you know, I'm not sure. But I think that for where I am right now, I want to continue to vote with my attention. And even when those feelings of doubt or regret crop up, to try and reground myself and the reasons why I chose this path and to choose to focus on what I'm gaining as opposed to what I'm losing.

Well, thank you for sharing that. And I love knowing that this is the seeds of your next book project. That's so exciting.

Yeah, I mean there's a pressure I think once you walk into the publishing world, always be working on something else. And I think there's a great irony that you know, I wrote the majority of this book on the side of a full time job and launching a book as you know, is a job in and of itself. And so I think for a just coming off of a few weeks of vacation and then break where I did a whole lot of nothing, but I'm trying to balance that desire to, you know, Always have the next thing. While also trying to ground and making sure that I'm giving myself enough time to recover after this past chapter.

Yeah, I joke that the first book signing I did for my first book, first question that the person standing in line asks, so, what's next? I and it was as if I just couldn't believe it. I didn't say anything, you know, I probably answered as best I could, but I'm like, oh my God, I've just worked for three years to get you this book and no sooner do you hold it in your hands than you ask what's next? And I feel like as well, yes, the publishers or my agent, they wanted me to write pivot 2.0 and I just couldn't do it. I was like, I can't. I gave it everything I have. I put everything I could into that topic. I said what I had to say on it. The Pivot method is complete. I have no 2.0 in me. And thus I went the new direction with free time. But it's true. I know you talk about a two word addition to the small talk question, what do you do? Which we will come back to. But I also feel like whether it's with family and oh, when are you going to have kids? Or when are you going to have the next kid or books? It's like, oh, what's the next one? It's like, but I just finished this one, you know, there is no next yet. It takes five years to launch a book properly.

Yeah. And it's hard to not have an easy answer to some of those questions. We want to be able to please people and say, oh, I know exactly what's coming. I know exactly what I want to work on next. I have three book ideas in my back pocket. But you know, I think there's a difference between other people's expectations and what you know that you need from your life right now. And I think a big part of the book for me, especially last chapter with K about status games, is how can you tune out some of that noise? How can you really get in touch with your intrinsic motivation and not just be motivated by the trappings of success or the potential awards or bonuses or promotions that might come if you play other people's games. Especially in this knowledge work economy where there's a lot of ambition and overachievers and people's accomplishments are on display for the world to see. It's really easy just to start climbing a ladder, even if it's not a ladder that you want to be on or to start playing a status game, even if it's a game that you don't want to be playing. And I think the tricky part is that it's so intoxicating. It's so nice to have an easy answer of what do you do? Or what are you doing next? Or what are your goals? Or where do you hope to be in five years? But you know, I think even when we have clear cut answers for the outside world, our internal experience is a lot murkier, or we're really honest with ourselves, we can have a good answer to the where do you want to be in five years? Question. But who knows what the world might bring?

One of the tricky things about that too is a topic I'm fascinated by that you address in the book as well. Oftentimes the quote price of success or the reward for success is more work. So whether you're working within a company and you're super efficient, if you want something done, give it to a busy person, as the adage goes. Or you talk about an attorney who gets a bonus based on billable hours. So the more efficiently she works, the more she has to work to meet the billable hours. Or when you're self employed, let's say, you're launching a book, let's say, and your book hit it, did well, you had a lot of attention from traditional media, which is amazing. And so in a way, the reward for that is you get more emails and more podcast invitations and hopefully speaking gigs and whatever else might follow that. It's this really tricky thing and I'm curious to hear your take on it. I haven't experienced it at super massive levels, but it's almost that this thing you're working so hard for to achieve success, when it arrives, the risk is that now you have two or three times as much work and you don't want to say no because you're like, but I work so hard to generate all this extra interest. And that's where I think another risk of burnout comes in.

Yeah, and it's true at an individual level and also true at a macro level too. You know, one of the stats that has stuck with me the most sincere porting the book, is that in the 1970s, the average American and the average German worker worked the exact same number of hours. And today the average American works 30% more than the average German worker. And the question is why? You know, this is sort of ahistorical. Typically the richer a country becomes, or the richer an individual becomes, the less they Work because they can frankly afford not to. But some of the greatest increases in work time over the past four decades have come from the highest earners. So the exact same people who could afford to work less are working more than ever. And the question is why? And I think part of it gets back to what you were just talking about as, you know, reward for success being more work is that we continue to take more and more onto our plates. K, who we mentioned from that last chapter, has this great quote where he says, you know, success is sort of like a drug and the first time you rip the bong, it's really easy to get high. But as you get more success or as you move up in your career, it takes more and more to get to that same feeling, and I think that's very true with professionals, is if you haven't invested in other sides of yourself, if you're not deriving meaning or purpose from other aspects of your life, you will have to get more and more success or prestige or accolades just to feel the same high that you're chasing.

You also give the example of professional athletes. I've always been interested in their career paths and pivots because it's so abrupt out of professional sports. They've run their whole lives, they've dedicated their entire lives to athleticism. And in a way that depends on youth, much like modeling would that for them. It was so powerful and really stopped me when I read in your book the athlete describing retiring from professional sports as being expected to go off of the drugs of adrenaline, attention, success and praise. Cold turkey.

Definitely. And you know, also there's another reference that I make to some athletes who have achieved their highest dreams or their highest goals. You know, there's a few famous cases of Michael Phelps for example, or Kevin Durant who once winning those Olympic gold medals or winning the NBA championship, they were set into a spiral of depression. The quote from Kevin Durant was, I dreamed the biggest dream that I could and then I achieved it. And now I'm left wondering now what now what's my purpose now where do I dedicate my attention? And so I think that's another risk is that you actually achieve what you wanted to retrieve and you realize the view from the top of the mountain isn't what it was cracked up to be.

We'll be right back just after this.

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So tell us about your two word addition to the rote small talk question. What do you do?

Well, it's kind of just a little anecdote from the end of the book, but you know that books about work and identity, and I think one of the biggest ways in which that's entrenched, especially in American culture, is the cocktail party conversation. So what do you do to kids? So what do you want to be when you grow up? I'm actually sitting right now in a friend's office and he was the one that told me this little addition of two words that he ties into that canonical piece of small talk, which is instead of asking people what do you do? Ask people what do you like to do? And it's so simple. But you know what I like about it is that it allows people to define themselves on their own terms. You can choose to answer that question with what do you like to do at work? Or what do you like to do outside of work? But it doesn't presume that our work is our identity or that our job title is the first way that we want to present to the world.

I love that. And it strikes me that part of the reason we're curious about what do you do? Is kind of how do you spend your days? As well, because we assume someone's probably at work. But that's not even true. So if I asked you if we met at a cocktail party and I said, so Simo, what do you like to do? How would you answer now, in this.

Moment, I would say that I like to write. I like to play ultimate Frisbee, I like to spend time outdoors and hike and invest in my local community. It's important that work is not absent from my Response? You know, writing, I feel very lucky to have found a career that I do enjoy and I do love. I think this has been interesting going on the podcast circuit and doing a lot of media about the book recently is that I'd be lying if I said that I didn't love my job. And to say care less about your job is not very actionable advice. And so what I tend to urge people to do is when you're thinking about how do you diversify your identity or how do you derive meaning from other aspects of your life, I don't think it's necessary really, about caring less about your job per se. I think it's more about making sure that you're investing in other sides of yourself, actively giving your time and your attention to other facets of who you are. Our identities are sort of like plants. They need time and energy to grow. And one of the risks of a work centric life is that you're giving all of your best time and all of your best energy to just one facet of who you are. And so that's what I try to encourage people to do, whether it's carving out one hour a week to go on a walk with their best friend and invest in a relationship, or whether it's spending five minutes a day learning a new language or picking up an instrument, not to try and master it or to become fluent, but just because it helps you connect with this other side of who you are, you find inherent pleasure, joy in the activity in and of itself. So rather than caring less about your job, I think it's more about making sure that you're caring about other things as well.

I can't resist asking about something in the introduction before we close out. You were typing the intro and you say, hell, I'm sitting here in a wework right now drinking from a coffee mug that says always do what you love. And I almost forgot to ask you about that because many of us listening have probably encountered a wework at some point or another and seen that emblazoned on the walls and big lettering and on the coffee mugs. What's your take on that mantra? Always do what you love.

Intoxicating. I definitely drink the Kool Aid myself. I thought about we work more than we do just about anything else, and how we spend those hours matter. And if I'm going to do anything for 40, 50, 60 hours a week, I might as well love it. But I think the problem with it, the way in which it becomes problematic, is when it creates this expectation that work should always be something that we love. And this is the problem with some of the rhetoric that we use around, you know, do what you love and never work a day in your life or a dream job. It just creates this expectation that work should always be a dream. And if you think about happiness as sort of the difference between your expectations and your reality, it can create a lot of room for disappointment. So that's one aspect of it. The second is something that I think a lot of us have learned recently in the past three years of the pandemic is that your job might not always be there. You know, you can love what you do, but if it becomes the sole source of identity and meaning and community in your life and you lose your job or it changes in some material way, what's left? It can be a very sort of narrow platform to balance on. And then the third is, you know, maybe a good note to end on, is the ways in which solely investing in our professional lives can neglect other aspects of who we are. The psychoanalyst Esther Perel has this great quote where she says, too many of us bring the best of ourselves to work and bring the leftovers home. And I remember the first time I heard that, it kind of hit me like a brick. Especially for people like you and I who do love what we do and are lucky to have aligned our ways of making money with our interests, what is the cost if we open up a laptop on Sunday or spend one extra hour at the office? We don't often think about that, but our other identities that exist within us need that time and attention as well. And if we don't invest in them, they can easily wither.

You gave a couple examples. But to that end, to close us out, if you could give listeners or invite them to do one small experiment in the next week after they're done listening, what would it be?

Something I've been thinking about a lot recently is the ways in which our identities are reinforced by the people around us. Classic example is if you're really good friends with your co workers and you go out to drinks with your co workers, you might inevitably find yourself talking about work. This makes sense. This is the context in which you know each other. And I think it's really important for people to find communities that can reinforce an identity of yours beyond the commercial value that you contribute to the world, beyond your professional life. So, for example, I love to play pickup basketball. And one of the great things about the pickup game that I play in is that people could care less about What I do for work doesn't matter how many books I've sold or words I've written that week. What they care about is that I am a good passer, that I show up on time to the game and I box out when I rebound. There are other value systems that exist and other containers to hold these value systems. And so my challenge, I guess, to listeners is how can you find a community in this next week where your job doesn't matter to them at all, where you can have another identity, whether it's your identity as a neighbor or as a citizen or as a friend or as a parent or as a sibling? You know, can you find a community this week where you can look around the room and people might have no idea what you do for work and that is okay?

I love that. Reminds me of furry friends as well. Like our pets don't give a what we do for work. It's just, are you available to play with me and be outside? Yes. Okay, check. Thank you so much Simo. This is such a joy to chat with you listeners. Be sure to get your copy of the Good Enough Reclaiming Life from Work if you don't already have it. And seema, where else would you like to send people to keep in touch?

The best place is just thegoodenoughjob.com you can find my social media and my newsletter, et cetera, there. But Jenny, it's such a pleasure to be on the show and especially as someone who is maybe on a similar trail but a little bit further down the mountain. It's been so inspirational to watch you in your journey and the way in which you've carved out paths for so many people in your wake.

Oh well, thank you so much. That means the world. And shout out to our mutual friend Sarah Peck, skp and I'm really delighted to connect as well. And listeners, I always say before we hit record, I'm like, I don't even want to talk too much. It's our first time meeting, but let's just hit record and you can join us in our coffee talk today. So thank you again Simo for the kind words and for being here. And big thanks everybody for listening.

Thanks so much for listening to this episode of the Pivot podcast. Make sure you don't miss an episode or my insider tips and templates by signing up for Pivot List, a curated twice monthly newsletter where I share the inside scoop on what I'm reading, watching, listening to and the latest tools I'm geeking out on. Sign up@pivotmethod.com pivotlist get show notes from this episode@pivotmethod.com podcast and connect with me on Twitter ennyblake.

Remember, build first, then your courage will follow. Hasn't it always.