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Worklife with Molly Graham

12 May 2026 · 37m · 13 chapters

Episode artwork

Why you should take a risk every day with Julie Zhuo

In short

Everyday risk-taking as a learnable practice; how to build courage through small, uncomfortable actions and how managers can create “safe” conditions for risk.

Guest background

Julie Zhuo, early design/product leader at Facebook during explosive growth; author of The Making of a Manager; co-founder of Sundial (AI for better organizational decisions). She describes herself as having been risk-averse, shaped by asthma and a childhood narrative about not being athletic.

Key claims

Risk shouldn’t be all-or-nothing (not just quitting jobs or big leaps). Confidence comes after doing scary things. Courage differs from fearlessness: acknowledge consequences and still act for a meaningful shared purpose. For feedback/boundaries, get “out of the emotionally heated zone” and ground in a positive shared future. Managers should bet on people, own outcomes, and align on values/success so teams feel safe to learn.

Notable examples

learning design at Facebook despite engineering background; enduring critique sessions; jumping into management; yearly “everyday risks” rituals (blogging publicly, speaking up, even trying surfing); saying “I’m not feeling good” or setting workout boundaries; quickly admitting when a hypothesis was wrong.

Written by AI. May contain mistakes.

Chapters

2:26

Understanding Everyday Risk-Taking

Julie Zhuo discusses the misconceptions around risk-taking at work and introduces the concept of small, everyday risks.

“Most of us think about risk-taking at work the wrong way.”
3:56

Julie Zhuo's Journey with Risk

Julie shares her personal experiences with fear and risk, highlighting growth through small acts of bravery.

“Today I'm talking to someone who has thought more carefully about the daily practice of risk than almost anyone I know.”
5:36

The Impact of Risk on Confidence

Molly and Julie explore how taking risks contributes to building confidence and the importance of stepping out of comfort zones.

“There's a lot of things that really scare me.”
8:00

Building a Practice Around Risk

Julie discusses how she developed a daily practice of taking risks and the rituals she uses to reflect and challenge herself each year.

“like, Hey, I'm, I'm not feeling very good right now.”
9:45

Examples of Everyday Risks

Julie shares specific examples of small risks she's taken, from public speaking to personal moments, emphasizing the variety in what can be considered risky.

“And so I'm really happy to hear that you think that I'm a great person.”
14:01

Embracing Everyday Risks

Learn about the concept of taking daily risks and how it can manifest in both big and small actions.

“that was where it went, but it kind of started from like one of those Januaries.”
15:26

The Craft of Risk-Taking

Discover how turning risk into a craft can lead to personal development and increased comfort with discomfort.

“And I think one big learning I had was like, it doesn't always look like the same outcome or activity.”
18:16

Agency and Ownership in Risk

Understand the importance of agency in choosing risks and how it impacts personal growth and fulfillment.

“The thing that I think is so cool about the way that you think about risk and what you've done is I do actually, I think people think of themselves as either good or bad at this.”
23:29

Navigating Risky Conversations

Learn strategies for engaging in difficult conversations and providing feedback effectively.

“uncomfortable, like pushing yourself to say the unsaid thing or to the feedback that would be so easy to just not say or the conversation that you can avoid having for months and it just grows and grows.”
28:01

Understanding Courage vs. Fearlessness

Explore the difference between courage and fearlessness in taking risks.

“It's like very hard to judge from the action itself, right?”
Show all 13 chapters
33:33

Management and Risk Taking

Discuss the role of management in taking risks and creating a safe environment.

“management, it makes you realize that those risks can feel really different depending on how much power someone has, particularly at work, but probably true in life as well.”
40:04

Reflecting on Personal Values

Learn to align personal values with professional decisions regarding risk.

“How do you think about risk in a situation like that?”
42:01

Finding Groundedness Amidst Chaos

Learn how to find sturdiness in decision-making amidst external pressures.

“It gives us a little bit more of like a framework or a grounding to then go into those decisions and to be able to, I think, feel sturdier.”
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Transcript

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0:36Toyota, let's go places.

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2:31Most of us think about risk-taking at work the wrong way. We imagine it as this big dramatic thing. Quit your job, start a company, say the thing that could get you fired. And yes, I will admit that I have probably helped cement that version of risk in my own TED Talk. Sorry. But that way of thinking about risk has a side effect. It becomes all or nothing. You're either a risk taker or you're not. If we think about risk taking that way, a lot gets left out. The question you didn't ask in the meeting because you were worried it would make you look stupid, the feedback you've been sitting on for two weeks, the boundary you've been meaning to set, we don't call those risks.

3:15We just call them things we didn't do. And here's what I've come to believe. The people who are actually good at taking risks didn't get there by making one giant leap, or even by taking big risks over and over again. They built a practice, small, uncomfortable swings over and over, not until it stopped feeling scary, but until the fear stopped getting in the way. I know that's been true for me. So today I want to explore, how do you actually get better at taking risks? And is it something that anyone can do?

3:55I'm Molly Graham, and this is Work Life, a show where we untangle the messy human side of work. Today I'm talking to someone who has thought more carefully about the daily practice of risk than almost anyone I know. Julie Zhu was one of the earliest design and product leaders at Facebook, where she helped build and manage teams through some of the most explosive growth in tech history. She later wrote The Making of a Manager, which has become a field guide for first-time leaders, and is now the co-founder of Sundial, a company using AI to help organizations make better decisions. Julie is a craftsman, and not just in design.

4:33When she wants to understand something, she dives in deep and builds a whole practice around it. For example, she did that with writing. One blog post a week for a year, and then landed a book deal. One of the things she has applied that craft to is risk, because she decided it was something she wanted to get better at. So I want to talk to her about what she did, what she learned, and what she really thinks it takes to be brave.

5:03Julie, welcome to Work Life.

5:05Molly Graham: Hi, Molly. Thank you for having me here. I'm so happy you're here. Oh, gosh. I'm so excited to be here. You've written about this idea of everyday risk and pushing yourself to take small risks regularly. I'm curious, like, what gave you that idea and why did you think it was important? I started to have this idea because I think one of the things that I'm worried about for myself, and in fact, I think I recognize about myself, is that I am just like a real scaredy cat when it comes to life. There's a lot of things that really scare me. And when they scare me, I sometimes have this inclination of like, okay, well, maybe that's not for me.

5:51Molly Graham: I can't do it. Somebody else is much better than that. And it got to the point where I started to see that as a pattern. But when I was little, I somehow got into my head that I was really not athletic. Like, in fact, I was just terrible at all things, physical, sports. I think maybe it was exacerbated by the fact that I had asthma. So my mom was always like very protective around me and, you know, going out and playing sports. And then my mom would have all these stories where she's like, well, I'm not really very athletic myself. In fact, I hate running. I hate sports. I hate this. And so maybe you inherited those genes in addition to the asthma.

6:26Molly Graham: So I just had this whole narrative that like these things were hard. And I think that, you know, I probably had this strong identity of like, okay, if I'm not good at sports, maybe I'm good at like things that use my brain. But in reality, what it was, I think, is that I was just kind of scared to try. Like I was scared to maybe validate the story that I'm bad at these things. And I think that that was a pattern that I had seen through many other things, right? And then at a certain point in life, when I look back, and I guess it was through, you know, the years I'd spent at Facebook and just being pushed to scale and try a lot of new things, I realized that when I look back, the things that made me proudest were when I did something that I didn't think I was going to do that was scary for me.

7:11Molly Graham: and I'm so proud. I'm so happy. Like I gained a lot more confidence. And I think that's often the price that we pay, right? The price of confidence is that you have to do things that you're scared of. And once I saw that pattern more and more, I was like, oh, I kind of want to like just do more of that. Like I realized now what's on the other side. So I started to lean a little bit more into that feeling of being scared. And so the goal that I had for everyday day risk is like, it doesn't have to be the big things. You know, it doesn't have to be like, I took a new job or I jumped off of a plane or I signed myself up for a marathon.

7:46Molly Graham: Sometimes it can be these little everyday things like, and they're just all around us. And so for me, an example of like a smaller way to do something I'm scared of is just saying a thing I'm kind of nervous to say like, Hey, I'm, I'm not feeling very good right now. Maybe, you know, when someone's like, how are you doing? Like, that seems a little risky because people probably expect me to say, oh, things are great. I'm fine. How are you? Or sometimes, you know, maybe I wish that I could relax and maybe not go and sprint the extra mile, you know, in my workout. Right. And it like sort of scares me because I'm not sure I can do it.

8:26Molly Graham: And whenever there's this feeling of like, I'm not sure I can do it, or I'm not sure how other people will feel about this, or I'm not sure like if I'm going to be comfortable, that's the feeling I'm starting to lean into a little bit more, which is like, oh, this is an opportunity for me to probably be proud or brave or whatever it is after the fact. Yeah. First of all, I just want to say, as someone that knows you, it's blowing my mind that you think of yourself as a scaredy cat because I actually think of you as very brave. But it sounds like you've turned that into a practice. It's something that you've taught yourself to be good at.

9:04Molly Graham: Yeah. Another way that I sometimes play the story in my mind, and of course we know that stories come and go, right, is I think I was forced to be brave in a lot of instances. Like, for example, coming to America and having to figure things out when I was at the age of six or coming and meeting my parents after I hadn't seen them for a very long time. And a lot of those things I look back and I'm like, yeah, I was really brave, but I don't feel like I had a choice in the matter. And maybe it took a lot out of me so that in other parts of my life, I wanted to stick to what was comfortable or what felt safe.

9:40Molly Graham: And now the older that I get, the more I'm able to, I think, push those boundaries a little bit more. And so I'm really happy to hear that you think that I'm a great person. I think that there have been cases where I look back, I'm like, yeah, that happened and I was able to do that. But there were also many times where I know that I was sticking to what felt more comfortable for me. And those are like the little boundaries that I now want to expand just because like, I know, it gets easier to do so when you practice over many years. Yeah, totally. One of the things that you said that really resonates with me is that confidence comes because of risk.

10:16I think sometimes people feel like you need to be confident and then you can take a risk. But you said like looking back on your time at Facebook, you realized that some of the things that you were proudest of were moments when you took a risk. Can you actually remember some of those experiences and tell me some stories of what you were so proud of that felt uncomfortable and scary at the time?

10:36Molly Graham: I think the first one was going and learning to be a designer. Because when I started at Facebook, I was hired as an engineer. I was trained as an engineer, computer science degree. And so I felt that that was what I knew. But what I really loved to do when I was in middle and high school was actually design. I didn't know that that was what it was called at the time. I just liked making websites. I liked going and opening Photoshop and creating images and then figuring out how to display those images on my website. But I didn't know that was a profession. I didn't know that was a thing you could do.

11:09I picked the closest thing I could, which was learning to code and learning engineering.

11:14Molly Graham: But once I realized that this was actually a thing that people did for a job, I was like, wait, I kind of want to do that. But I had no formal training in design. And so when I first joined the design team and everybody's like talking about typography and they'd like studied all this. And I remember even getting into a conversation about like Macs versus PCs. And the entire design team was like utterly convinced that Macs were so much better designed. And I never used a Mac. Like all I knew was PCs. And I was trying to be like, no, no, they're not so bad, like blah, blah, blah. And like people were just like, who are you?

11:45Molly Graham: And like, what are you doing here in this club? So I was proud that I was able to start to learn some of those skills and get the grounding and start to push myself in showing designs and getting critique and all of that. So actually even critique in of itself as a design practice is essentially where you come up with something and then you show it to a room of designers. And the entire goal is the room is going to go around and kind of tear it apart and show you all the things that you weren't thinking about. And that was like terrifying to me. And so practices like that, like showing up over and over to do that was really, I think I look back and I'm like, I'm really glad I did that, even though I was so nervous and it was really hard at the time.

12:29Molly Graham: I think also jumping into management was an example. I was asked to manage and I was just like, sure. But I had no idea what it really entailed or what that meant. And just the next couple of years were just me feeling like I didn't really know what I was doing and all one-on-ones felt awkward and trying to figure out how to do things for the first time. whether it was like give an offer for the first time or negotiate for the first time or tell someone that's not working out for the first time. Like all of these were hard and I felt scared. Yeah. I am curious though, like it sounds like you built that practice at Facebook and you started to learn how powerful it was to take risks.

13:14And then you realized that you weren't naturally doing it. You had to push yourself to do it. And so I know what, I think one year you built a daily practice around risk. Will you just explain some of that?

13:27Molly Graham: Yeah, I do challenges for myself every year. I love January. I love the chance to sit down and reflect and think about what we learned last year and what should we think about and dream about for the year ahead. So I have this magical set of rituals around January. And every year I try to do some things that I think will be kind of fun, but be kind of challenging. And there was one year that I decided to blog and write publicly for the first time. And that was how I started writing on the internet, which eventually led to like writing a book. And I couldn't have predicted that was where it went, but it kind of started from like one of those Januaries.

14:05Molly Graham: I think about two years ago was when I was like, this will be the year of everyday risks. And I like try to come up with a little title on a theme for every year. So sometimes there were bigger things and sometimes there were like smaller things, like speaking up in a room or like trying to tell everyone else to like be quiet because like we actually need, you know, to listen to X person or I need to say something or, you know, bigger ones would be like I went and tried surfing for the very first time, which was also something that terrified me. But it's a blend, right? It's not like all big things.

14:37Molly Graham: A lot of it is very little things. Like sometimes it felt risky to actually take a break and to spend instead of like following my schedule, it felt riskier to be like, no, no, no, I'm actually just going to take this two-hour block and I'm going to do something with my kid. So it's a feeling more than it is like a particular action because sometimes following a plan when you don't want to feels kind of risky. Sometimes following a plan when you actually kind of want to do something else is the thing that feels risky. So I was leaning a little bit more into how it felt more than what was the specific task.

15:13It sounds like from naming it and reflecting on it, it made it easier to identify both like what felt risky and when you should take a risk.

15:25Molly Graham: That's right. Yeah. And I think one big learning I had was like, it doesn't always look like the same outcome or activity. Like it's not always, oh, I need to speak up more in this context. Sometimes it's like, maybe I need to not say something, even though I really, really want to, but maybe it'll actually, you know, be better. Or it's like me learning something to not say something in this case. So it's very much about trying to follow that feeling more than it is about being very specific. I think that's probably one of the things that I learned the most from that year. If you look at my journal, it's all a very different variety of activities, sometimes conflicting with each other week over week.

16:07It's so interesting. I think of you as such a craftsman. It's actually the word that came up for me when I was thinking about you and thinking about talking to you today because obviously you're a designer and you're a craftsman because of that. And I feel like your book was actually all about taking management and turning it into a craft. And it actually turns out that what you did with risk is try to turn it into a craft, like believing that it was something you could actually get better at through a daily practice. I am curious though, like what impact did it have on you? Like what did it unlock for you to actually like name it and see it?

16:47Molly Graham: I think about like, it's training a muscle, you know, which is also one of the things I'm doing now in my, my, my later years is like actually getting more athletic and doing more sports and things like that. But yeah, like I, when I first started, like I couldn't do a single pushup, like it's been years since I've been able to do a single pushup and it's not easy to do the first, but after you do the first and like the second is easier and the third is slightly easier. So the, the distance between them gets easier, the more you do. And I kind of love that feeling. I remember in Dante's Inferno, there's like a beautiful analogy that like, you know, towards the second half, like eventually it's like so hard when you're like in the pit, but then when you walk yourself up, eventually the higher you go, the like faster you go until you're finally flying.

17:29Molly Graham: Right. And I just love that analogy because to me, like, that's how I think about it. Like at least in my mind, I'm like, okay, it is hard, but like, if I can do more and more of them, when I look back, it's like the number of risks that I might be taking like now compared to three years or five years ago, like it feels, it's, it always still feels like the edge of it still feels like kind of uncomfortable and like a little, you know, sharp and jagged, but on the whole, it just feels easier to do because it feels like I've built up that capacity. Like I've trained more of the muscle. But the good thing about life is it's always meeting you with like more and more things.

18:06Molly Graham: So it kind of just when you're like, oh yeah, that kind of thing becomes easier. It's like the boom, it's like the next challenge, the next challenge, next challenge. And I think that's life. Totally. That's the joy and the torture. The thing that I think is so cool about the way that you think about risk and what you've done is I do actually, I think people think of themselves as either good or bad at this. Like I am not a risk taker or I am a risk taker. And you built a practice that said, I can get better at this, which is like such a powerful thing. And the other thing is like, you're naming something I really believe, which is that it never goes away.

18:41Like you might get better at one type of thing, or it might get easier maybe to like step into that discomfort, but it's not like you can ever live a life without the opportunity for risk. So actually just what you get better at is like recognizing, oh, I'm feeling that way again. And it's like, I got to get cool with the discomfort again.

19:01Molly Graham: I also think, Molly, there's such a big difference between the risk that you sign up for or the choices that you make. The agency matters a lot. I mentioned earlier, I felt like I had to be brave because circumstances were such that it sort of asked that of me. I didn't get to choose whether or not we were going to move from China to America. I kind of had to, and then I had to deal with it. And even when I was at Facebook, I chose Facebook, but I didn't necessarily, you know, I felt like these opportunities were sort of both either asked of me or like, you know, I was nudged in that direction.

19:35Molly Graham: Or you could even argue it was like peer pressure because I was like around so many incredible people and I just felt like I wanted to keep up in some way. But more and more, I find that it makes a big difference if like, I'm like, no, I'm going to try this. I'm going to try this for me, not because someone else is trying to push me into it or nudging me into it or saying that this is the way it should be or that this is what's good for me. It's like I opt into it. And I think regardless, either way, if you opt in, it's going to be hard, but at least you know you chose it. If you don't opt in, life's still going to give you a bunch of things as well.

20:09Molly Graham: So, you know, like all things being equal, I think there's something that comes from feeling like I am in the driver's seat of like getting to choose the kinds of things that are hard for myself. And I think there's a lot of joy in that.

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23:28One of the examples you gave earlier of the daily risks was saying something that was uncomfortable, like pushing yourself to say the unsaid thing or to the feedback that would be so easy to just not say or the conversation that you can avoid having for months and it just grows and grows. So what have you learned from turning that into a practice, turning that into a craft? What have you learned about what you need to do in those situations when you disagree with someone or when you need to give someone feedback that's a little scary?

23:58Molly Graham: Yeah. Great question. The first thing I've learned is I need to be out of my emotionally heated zone. That's the most important thing. I've come to realize that whenever there's a feeling, there's something good in that feeling. Let's say you and I are talking. This will never happen with you, Molly. But like, let's say you're talking and I'm like real angry about it after the fact. There's a good reason usually, right? There is a good reason. There's something that's bothering me about that conversation. And there's like something good and pure there. But if I'm angry right now, I just, there's no way we can find the kernel of what was like really important about why it bothered me in that moment.

24:39Molly Graham: And the way I express it is always going to sound like kind of egotistical, right? Because it's about like my hurt, my anger, and like, why are you doing that thing to me? And like, it's just, there's no way I can communicate that and give it kind of the like attention and the best chance of like making it something productive. And so that's the most important thing is like awareness of like, wait a second, am I in like a negative headspace right now? Because if I'm in a negative headspace, this is not the time. Like maybe I can journal, maybe I can like, I don't know, try to process it a little bit, but let's like come back to it when I'm feeling more ground.

25:14Molly Graham: And what grounded feels like to me is like, I'm thinking about the bigger picture. Like I'm thinking about something positive that I truly care about, right? Not my ego, not that I'm hurt and angry. Why did Molly do this thing to me? But like, I want us to create something great together. I want our team to be wildly successful. I want our team, I want our company to hit its goals. You know, I want our relationship to be better for the long term. If I am now starting to think in that zone and that's my why, then I am ready to figure out what is the kernel of whatever it was and find a way to talk about it.

25:51Molly Graham: So that's at least my personal litmus test. So it matters for that relationship. It matters that we can, for my values, that we can be the kind of people who we don't bury issues. We don't pretend like everything's good because it's still there. Like I can still feel the energy and I want to resolve that. Like I want to feel like you can trust me and I can trust you. And like, that's the why. Yeah. It's so interesting because I think you use the word grounded. And what I hear is like, you need to be grounded in a positive vision of sort of like the future and what you want that has nothing to do with being right and has nothing to do with like, it is about the outcome because you're trying to create like a more positive relationship, but it's not about like the outcome you want necessarily or like, yeah, to your point, like your ego.

26:36It's about the fundamental thing underneath it that you're trying to accomplish.

26:40Molly Graham: Yes, that's right. It's not about like making me feel better in that moment, right? It's not about like removing a wound. It's not about validating that I'm right or I'm great or I'm whatever it is. We're building something collaborative and shared together because we both want a positive and creative vision of the future. Yeah. Okay. You've gotten really good at pushing yourself to take risks. I'm curious, how do you know when you shouldn't? How do you know when it's something you shouldn't do? One thing you said was when you're in emotions and anger, but just more broadly too, when shouldn't you?

27:22Molly Graham: I think, yeah, it's what you mentioned before. I think we have to ask ourselves, why are we doing this? I know some people for whom whenever something gets hard or something gets scary, they kind of want to change everything about their lives. Do you know what I mean? They want to move to a different city and they want to break up with someone. And it's actually not related. It's like there's something that's scary and maybe the instinct is actually to flee or run. And it seems like taking risk, but in some ways it's actually a pattern. It's opposite of risk. It's doing the thing that they're used to doing because it feels safer somehow to do that.

28:05Molly Graham: I think that if it feels like it is getting grounded in some kind of fleeing or some kind of avoidance or some kind of trying to get away from a negative feeling or reaction, and it's done when we're still feeling those things, then it might not be the kind of risk that serves our long-term purpose. Yeah. It's very hard. I've learned this. It's like very hard to judge from the action itself, right? Sometimes like what often looks to the outside of like, oh, that person is so brave. Like, you know, I've read somewhere that there's like a real distinction between like having courage and being fearless.

28:45Molly Graham: And fearlessness is this idea that like You're doing it because you're not afraid to do it because it just never, I think it wasn't really ever scary. Maybe it's even intoxicating in some way, right? Whereas courage is a little bit more grounded. Courage is like you are aware of what all the consequences and ramifications might be, and it is scary. There's no guarantee that they won't happen, but you believe this is important because you're doing it towards some greater end. So even though you will still feel scared, you're still taking that step anyway. Dude, I love that. I love that definition.

29:22I've never heard the difference between fearlessness and courage, but it really resonates with some of the stuff you said around just like being grounded in what's making you afraid, but also in what you want. And if you have that, then you can take a risk knowing why. Right. Yeah.

29:41Molly Graham: Yeah. I genuinely think most people think I'm either good or bad at this and that's like a fixed thing inside of me and my life and my personality. I'm either a risk taker or I'm not. And you've made it a practice of something that you are trying to get better at. And I think you can like unlock that for people, which is that this isn't a fixed thing. This is something that you can practice daily, you know, or weekly. Yeah, I do feel that way. I think that like I used to be a very risk averse person. And I don't feel that way anymore. So, you know, it's just like there's definitely growth.

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33:32One of the things I really wanted to talk to you about, because you wrote a book on management, it makes you realize that those risks can feel really different depending on how much power someone has, particularly at work, but probably true in life as well. I'm curious how you think about the role of management and risk.

33:54Molly Graham: So I think that what a manager needs to do is bet on certain things. And so when you bet on something, that means you do have to own it. You have to own the responsibility for how it goes. But the decisions are less about exactly what we should do in a lot of cases, but who should we trust? Who knows the best amongst our group what to do in this case or what great looks like here? and therefore they should be the ones made decision. But I also think it's super important that if it doesn't go well, you kind of have to own that outcome as well, right? Because at the end of the day, you made the bet.

34:29Molly Graham: Like, you know, if I said, hey, like, I think that when it comes to this issue, you know, George on the team has the most context. Like, let's follow his lead. He says, we're going to go with this decision. We follow the decision, right? I think mistake number one is like, if I believe I know better than George and then I'm like, no, we have to do this. But it turns out George is better. There may be some cases in which like maybe I do know better than everyone in my team and therefore I should make the decision. It's not that I think micromanaging is always wrong. It can be like the right thing to do if you truly do know better than everyone else on your team.

35:01Molly Graham: But at that point, like, you know, maybe you should be hiring a better team or like, you know, maybe there's something else that's going on in terms of the structure. It goes back to like, I think good management is really about just being very aware and like continually testing your judgment against reality and being open enough to see when things are or aren't working. I think that at the same time, I think it's about trust as well. So like in this case, like George has to feel that I am on his side. Like I am doing whatever I can to help him succeed and do my best until again, new information emerges that it was ultimately the wrong judgment call to make.

35:40Yeah. I'm curious like what you think about the phrase like safe space or something like that. Cause like, I do think one definition of a great manager is someone who makes it safe for a team to take risks or an individual to like put themselves out there and try things that are scary or they might not be good at or to advocate for something. And a bad manager is someone that like can make everything inside of that feel risky or like your whole reputation is on the line. Do you think safety is sort of like a part of what great managers create?

36:15Molly Graham: Absolutely. I think it's really important for people to feel like it's okay sometimes that we try some things and they don't work out. One of the things that I tell my team right now, we're all in this very, I think, intense AI period where it feels like every single week things are changing, the way teams work are changing, the technologies that are coming out and what it enables are changing at such a rapid clip. And so in those cases, I think often people ask these questions of like, well, what's the world going to be like in three months or six months? What really matters? What are the big bets?

36:50Molly Graham: And to be honest, I don't know that I know. I don't know that a lot of people in this world really can say with any amount of great certainty what will happen in some number of weeks or months or years. And I think to pretend otherwise is not doing the team or anyone a service. So in those cases, what I told my team is, you know what, this is the time for us to try a lot of things and to take risks. The thing that I would ask of you is that we're here to learn. And so if you have a great idea and you have a hypothesis as to why this is going to be great for our product, our company, I want you to feel like you can take that, right?

37:29Molly Graham: I also want you to know it's okay if you're wrong. But what I'm going to ask of you is, if you are wrong, I'd like you to be the person most obsessed with figuring out as quickly as possible that you were wrong. I'd like you to be the first person to say, hey, I tried this thing and I thought it was going to do this, this, this, and then I went and had a good go and it turned out that, you know, this isn't the right path for us. Let's do something else. That still allows people to take risks, but do so in a way where we all feel like we have the team's best interests in mind, right? So it's really important.

38:04Molly Graham: I think that when I think about the dynamic in a team, like, you know, we can't take risks if we feel like there's always going to be a evaluator or judge who is just looking at our every single move. It doesn't feel good. It's like someone's just like big brother is watching you and it's like, hmm, did you do this enough? Did you do this? And they're like looking at your activities or your behaviors and assessing whether or not you're here, you're going to make it. But I do think that what's important is this sense of trust. And what trust comes down to is like, do we see things in the same way?

38:38Molly Graham: Are our values aligned? Do we both understand what success looks like? I think that's such an important question, right? That what I believe is success for the team and what everybody on the team believes is success for the team. If that is unified, if that's like we're on the same page, we all know what we're trying to shoot for, as well as we all know what values are there, right? Like, what does it mean to work in a way that's respectful? What does it mean to kind of shoot for excellence? Like, how do we treat each other when things are hard? Like these are all what I mean by like base values.

39:12Molly Graham: I think if those two things are good, then you know what? People should have more and more freedom. Like I really believe in that level of empowerment because that's what like I had people to do is like, is just to go and do their best work and use all that talent and skill and brain power and collaboration to make something that makes our team better. Yeah. But I am curious because not everyone in the world has like done the work to think through what does it mean to be a manager? What does it mean to sort of like get the most out of the team? And I think a lot of people are like trapped in work situations where a manager makes things feel unsafe or makes things, you know, a lot of those like day-to-day risks that you talk about feel scary, including like giving feedback or setting a boundary or saying, I'm not going to work, you know, at night.

40:03Like some of that can feel like your job or your reputation or your, you know, to your point about performance reviews, like that's on the line. How do you think about risk in a situation like that? Like how do you actually influence or work with or like how would you tell someone to think about risk in that situation?

40:23Molly Graham: I think that for all of us, especially now in an era where things feel very uncertain in terms of like what's the future going to hold, what's going to happen with technology, I think the most important thing for everyone, whether you're a manager or whether you're somebody who is on a team and you're worried about the environment of your team, to, I think, take a step back and to ask ourselves, what really matters? It's sort of like the meta level, right? So we talked a little bit about sort of more maybe bounded areas. Like when you're a team, you're like, what does success look like for a team?

40:55Molly Graham: But if we step back, we're like, what does success look like for my life? What really matters to me? Again, it goes back to what would I consider if I look back 20 years from now, 50 years from now, that I would have been proud to do? What is it when I look back and think about my values? How do I want to work? How do I want people to treat each other? What do I care about? And I think when we think like that, it's very generative. It feels like it comes from a very energizing and generative place, which is great. That's kind of the energy that we want to go into sometimes these harder decisions.

41:29Molly Graham: Like we want to kind of come from what is like our purpose? Like what do we care about? What do we want to be a part of? I think what can happen is that, you know, in the day-to-day, like something can happen and we can often get very reactive about it, right? So for example, to your point, this example of like, hey, I don't really want to work this weekend or tonight because like something else is really happening in my life that really matters to me, you know, maybe it's family, it's whatever. And I think if you're able to zoom out and ask yourself, okay, no, like 20 years from now, what's going to be important?

42:01Molly Graham: It gives us a little bit more of like a framework or a grounding to then go into those decisions and to be able to, I think, feel sturdier. Sturdiness is kind of, I think, this like sense of groundedness. It's like, you know where you stand for, you know where you come from. And therefore, when other things kind of react, right? And other things reacting kind of feels like, you know, in my mind, like weather. It's like there's wind that's blowing. There's a storm. There's this, there's that, right? And it impacts us. For sure it does. It can make it very difficult for us. But if we can then take a moment to be like, okay, but what is the value that we have?

42:35Molly Graham: For me, it's like I want to go back and feel like as much as I love my job and working and being a startup founder, I don't want to look back in 20 years and feel like I miss time with my family and my kids and the people who are close to me. Like I let friendships, you know, wilt or whatnot. Right. So, so sometimes just like having time to ask those questions and then be like, okay, so now this thing is happening, you know, like, yes, there is an urgent work task. What really matters? It becomes easier. Again, our decisions are always going to be very personal. You know, what I decided will be very different than like what you or somebody else decides.

43:12Molly Graham: But I think as long as we know ourselves more deeply, it will become easier for us to be able to then take that risk or do the thing that feels a little bit scary in that moment because we know why we're doing it. Like, what does it really ladder up to in the long stretch of time? Julie said so many brilliant things that I want to remember. One is something I believe that is still kind of blowing my mind, which was the difference between fearlessness and courage. Because sometimes I think we think like, oh, the goal is to be fearless. But she defined that as acting without fear, which can actually be reckless, right?

43:51To not be afraid of things that are actually scary. But she said that courage is being aware of your fear, being aware of the consequences of what could happen that's bad, but still acting because it's important and because there's this positive shared purpose that you're trying to build towards. And that makes you realize that the goal is courage, right? The goal is to have the courage to do the things that are important. And wouldn't we all be a little bit better off if we did that every day or every year?

44:31Work Life is a production of Ted and Pushkin Industries. This episode was produced by Isaac Carter and Leah Rose. Banban Chang is our story editor. Mixing by Hansdale Shi. Ted's executive producer is Daniela Balarezzo. Constanza Gallardo is the executive producer for Pushkin. Special thanks to Roxanne Hilash, Valentina Bohanini, Laini Lott, Tansika Soongmanivong, and Ashley Murphy. If you like the show and want more, come join the discussion on my Substack lessons. I'm Molly Graham. Thanks for listening.

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From the publisher

When you think about risk, you probably think about big, dramatic moves: quitting your job, moving across the country, saying something controversial. But the people who are actually good at taking risks are the ones who practice small challenges every day. Julie Zhuo was one of the earliest product and design leaders at Facebook, and is now the co-founder of Sundial, a company that uses AI to help organizations make better decisions. In this episode, Molly and Julie dissect what it actually means to take a risk and how you can build your risk-taking skills through daily practice. Julie reflects on her own risk-taking journey, the ways she has honed her abilities to challenge fear, her thinking on when you shouldn’t take a leap, and the important distinction between courage and fearlessness.


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