Why you should take a risk every day with Julie Zhuo | from WorkLife with Molly Graham
37 min
•May 25, 2026about 2 months agoSummary
Julie Zhuo, former Facebook design leader and author of 'The Making of a Manager,' discusses how risk-taking is a learnable skill developed through daily practice rather than an innate trait. She shares her personal journey of building a deliberate practice around small, everyday risks and explains how managers can create psychological safety for teams to take calculated risks.
Insights
- Risk-taking is a trainable muscle, not a fixed personality trait—people become better at it through consistent small uncomfortable actions, not dramatic one-time leaps
- The distinction between fearlessness (acting without fear, potentially reckless) and courage (acting despite fear toward a meaningful purpose) fundamentally changes how we approach risk
- Psychological safety in management requires alignment on shared values and success metrics, not just absence of punishment—teams need to know their manager is on their side
- Personal risk-taking becomes easier when grounded in long-term values and purpose rather than reactive emotions or ego protection
- Managers should bet on people and trust their judgment, then own the outcomes—micromanagement signals a lack of trust and prevents team growth
Trends
Shift from viewing risk as binary personality trait to viewing it as a developable skill through deliberate practiceGrowing emphasis on psychological safety and trust-based management over command-and-control leadershipRecognition that small daily risks compound into significant capability building over timeIncreased focus on values-alignment and long-term purpose as drivers of courageous decision-making in uncertain environmentsAI era creating urgency for organizations to foster risk-taking cultures to enable rapid experimentation and learningDistinction between chosen risks (agency-driven) versus forced risks (circumstance-driven) in building resilience and confidence
Topics
Daily risk-taking practice and skill developmentPsychological safety in team managementCourage versus fearlessness in decision-makingValues-based leadership and long-term purposeFeedback delivery and difficult conversationsEmotional regulation before high-stakes communicationTrust-based delegation and team empowermentGrowth mindset and capability buildingManagement philosophy and team dynamicsDecision-making under uncertaintyPersonal identity and limiting beliefsCraft-based approach to skill developmentVulnerability and authenticity at workAgency and choice in risk-takingRapid experimentation in AI era
Companies
People
Julie Zhuo
Guest discussing her framework for building a daily risk-taking practice and philosophy on courage-based leadership
Molly Graham
Host conducting the interview and drawing out insights about risk-taking and management
Quotes
"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."
Molly Graham•Early in episode
"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."
Julie Zhuo•Mid-episode
"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."
Julie Zhuo•Mid-to-late episode
"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 it turned out that this isn't the right path for us."
Julie Zhuo•Late episode
"What really matters to me? Like, again, it goes back to like, what would I consider if I look back 20 years from now, 50 years from now that I would have been proud to do?"
Julie Zhuo•Closing segment
Full Transcript
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Most 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. We 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. Today I want to explore how do you actually get better at taking risks? And is it something that anyone can do? I'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 Zoo 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. When 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. Julie, welcome to Work Life. 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. 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 going out on planesports, and then my mom would have all these stories of 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. So I just had this whole narrative that like these things were hard, and I think that 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 that was a certain point in life when I look back, and I guess it was through the years I had 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. 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 realize 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 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. 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 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. 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. Yeah. Another way that I sometimes play the story in my mind, and of course we know that story is 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. 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 am a brave person. I think that there have been cases where I look back and 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 I don't get easier to do so when you practice for many years. Yeah, totally. One of the things that you said that really resonates with me is that confidence comes because of risk. I 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, like, what you were so proud of that felt uncomfortable and scary at the time? 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 like 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. I picked the closest thing I could, which was learning to code and learning engineering. 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 talking about typography and they had studied all this. And I remember even getting into a conversation about 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. All I knew was PCs. And I was trying to be like, no, no, they're not so bad, blah, blah, blah. And people were just like, who are you? And 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 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. 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 like the next couple of years were just me feeling like I didn't really know what I was doing and like all one-on-ones felt awkward and like trying to figure out how to do things for the first time where there 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. And 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? Yeah, I do challenges for myself every year. I love January. I love like the chance to like sit down and reflect and think about like what we learned last year and what should we think about and dream about for the year ahead. So I like have this like magical set of rituals around January and every year I try to do some things that I think will like, you know, be kind of fun but be kind of challenging. And like 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 January's. 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. 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. All right, so it's a feeling more than it is like a particular action because sometimes, you know, 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. It 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. 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 again, it's like 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. Like if you look at my journal, it's like it's all a very different variety of activities, sometimes conflicting with each other week over week. It'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 Takini 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? I think about like as training a muscle, you know, which is also one of the things I'm doing now in my later years is like actually getting more athletic and doing more sports and things like that. But yeah, like when I first started, I couldn't do a single push-up. Like it's been years since I've been able to do a single push-up 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 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 finally fly, 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. Yeah. But the good thing about life is it's always meeting you with like more and more things. 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, 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. Like 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 gotta get cool with the discomfort again. I also think Molly, there's such a big difference between the risk that you sign up for or the choices that you make. Like the agency matters a lot. Like I mentioned earlier, like I felt like I had to be brave because circumstances were such that it sort of asked that of me. Like I didn't get to choose whether or not we were going to move from China to America. Like 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 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. Like I'm going to try this for me, not because someone else is trying to push me into it or, you know, nudging me into it or saying that this is like 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, like 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. 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. Hi Derek, Tara from Flash Designs here. Hope you well. Not sure if you've seen my emails from last month, but could you please pay my invoice? Thank you so much. Bye. Hi, it's Tara, Flash Designs. Did you get my last voicemail? I know you're busy, but please pay my invoice today, if possible. Hello again. It's Tara again. Politely nudging again. Still chasing unpaid invoices. Let's say co-pilot helped you the chase and so you can get paid up to seven days faster. Search Sage Accountant today. One of the examples you gave earlier of the daily risks was saying something that was uncomfortable, like pushing yourself to like say the unsaid thing or to like, you know, the feedback that would be so easy to just not say or the conversation that, you know, you can avoid having for months and it just grows and grows. So like, what have you learned from turning that into a practice, turning that into a craft? Like, 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? Yeah, great question. The first thing I've learned is like, I need to be out of my emotionally heated zone. That's like the most important thing. So, you know, like, I've come to realize that whenever there's a feeling, it's like there's something good in that feeling, right? Let's say, you know, you and I are talking, this will never happen with you, Molly, but like, let's say you're talking and I'm like, really agree 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. 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. 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, then 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 like figure out what is the kernel of whatever it was and find a way to like talk about it. So that's like, at least my personal litmus test. So it matters for that relationship. Like it matters that we can, you know, for my values that we can be the kind of people who we don't bury issues. Like 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. Yes. It 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. Yeah. It's about the fundamental thing underneath it that you're trying to accomplish. 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 like, how do you know when you shouldn't like, how do you know when it's like something you shouldn't do? Like one thing you said was like when you're in emotions and anger, but like just more broadly too. Like when shouldn't you? I think so. Yeah. It's what you mentioned before. I think we have to ask ourselves, why are we doing this? Like I know some people for whom like whenever, you know, something gets hard or something gets scary, they kind of want to like change everything about their lives. Do you know what I mean? Like, you know, they want to move to a different city and they want to like, you know, break up with someone and like, and it's actually not related. It's like, there's something that's scary and maybe, you know, 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. Like it's doing the thing that they're used to doing because it feels safer somehow to do that. Right. I think that if it feels like it is getting grounded in some kind of fleeing or some kind of like 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. And it's 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. And fearlessness is this idea that like you're doing it because you're not afraid to do it because, you know, it just like never, that thing wasn't really ever scary. Maybe it's even intoxicating in some way. Right. Whereas like 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. I've never heard the difference between fearlessness and courage, but it's, you know, it really resonates with some of the stuff you said around fearlessness. You know, 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. I genuinely think most people think I'm either good about it, 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 there's definitely growth. At New Balance. We believe if you run, you're a runner, however you choose to do it. Because when you're not worried about doing things the right way, you're free to discover your way. And that's what running is all about. Now, please. The Holland and Barrett have announced something big. Hey, keep breathing. The wellness day sale. Thousands of offers on wellness favourites and it starts at 13th of June. Now relax. That's going straight in my diary. Back your body for less with Holland and Barrett. Here first in the HMB app, sell runs 13th to the 16th of June. Exclusions and teas and teas apply. Since 1926, Steel has been developing tools that make working in nature easier. From forests to gardens, Steel tools are made for people like you who work like a pro, mastering every challenge with heart and soul. For 100 years, the Steel name has stood for revolutionary technology with a passion for legendary performance and quality. Built for nature, trusted since 1926. Find your tool at steel.co.uk. One of the things I really wanted to talk to you about, because you wrote a book on management, it makes you realise 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. So I think that what a manager needs to do is bet on certain things. So when you bet on something, it means you do have to own it. You have to own the responsibility for how it goes. So I think that what a manager needs to do is bet on certain things. So when you bet on something, it 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 who 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. Because at the end of the day, you made the bet. Like, 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. 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. And 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. Yeah. I'm curious, like, what you think about the phrase, like, safe space or something like that. Because, 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? 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. Like, one of the things that I tell my team right now, you know, we're all in this very, I think, intense AI period where it feels like every single week things are changing. Like, 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 work going to be like in three months or six months? Like, what really matters? What are the big bets? And to be honest, like, I don't know that I know. I don't know that a lot of people in this world really can stay 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 as service. So in those cases, what I told my team is, you know what, like, 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 or company and what you're going to feel like you can take that. 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 ahead 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. I think that when I think about the dynamic in a team, like, you know, we can't take risks. 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, you know, 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 like trust and what trust comes down to is like, do we see things in the same way? 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, you know, 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. Like, how does it, 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. 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, you know, and, you know, use all that talent and skill and brain power and collaboration to, 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, and I guess 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. Like, 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? I think that for all of us, especially now in the 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, whether you're somebody who's on a team and, you know, you're worried about like 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, we talked a little bit about like, sort of more maybe bounded areas, like when you're a team, you're like, what does success look like for a team? But if we like step back, like, what does success look like for my life? What really matters to me? Like, again, it goes back to like, 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? Like, 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. Like, it feels like it comes from a very energizing and generative place, which is great. Like, that's like kind of the energy that we want to go into. Sometimes these like harder decisions, 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? 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? Other things reacting kind of feels like, you know, am I 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, you know, 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? Like for me, it's like, I want to go back and feel like, you know, as much as I love my job and working and like being a startup founder, like I don't want to look back in 20 years and feel like I like 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 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. 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 is 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? To 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? Work 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 Hans Dale Shee. Ted's executive producer is Daniela Ballerazzo. Constanza Gallardo is the executive producer for Pushkin. Special thanks to Roxanne Hylash, Valentina Bohanini, Laini Lott, Tansika Sungmanivong, and Ashley Murphy. If you like the show and want more, come join the discussion on my sub-stack lessons. I'm Molly Graham. Thanks for listening. Stripe is built for whatever comes next, and Stripe Billing is ready for your next business model. You can easily test and iterate subscriptions, or launch the latest usage-based and hybrid pricing models like some of the fastest-growing AI companies in the world. In fact, Stripe powers all of the Forbes AI50 who have monetized. Learn how you can power any business model at stripe.com. Hey podcast peeps! Right, is anyone else out there mad about photos? I have thousands on my phone, so here's a hack. I've been printing my photos. 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