Overview
This episode is about risk at work, but not the headline-grabbing kind. Molly Graham and Julie Zhu talk about risk as a daily practice: asking the awkward question, giving the feedback you've been avoiding, setting a boundary, or saying what you actually think.
Julie argues that bravery is less a personality trait than a skill you build through repetition. The point is not to stop feeling fear. It is to stop letting fear run the decision.
Key Takeaways
Julie’s main idea is simple and useful: confidence usually comes after the scary thing, not before it. She says the moments she is proudest of are the ones where she did something she did not think she could do. That changed how she sees discomfort. Instead of reading fear as a stop sign, she treats it as a clue that there may be growth on the other side.
She also pushes back on the idea that people are either "risk takers" or not. In her telling, risk works more like a muscle. Small reps matter. A person gets better by taking manageable risks over and over, whether that means speaking honestly, trying something unfamiliar, or resisting the urge to stay inside an old identity.
Another strong point is the difference between chosen risk and imposed risk. Julie says she has had to be brave in life because of circumstance, but there is a different kind of energy in choosing the hard thing for yourself. Agency changes the experience. You may still be uncomfortable, but you are in the driver's seat.
On communication, she is clear that timing matters. If you are angry or flooded, do not rush into the hard conversation. There may be a real issue underneath the feeling, but you need enough distance to find the actual point instead of lashing out from hurt.
The management section adds a second layer: risk is shaped by power. Julie says managers are constantly making bets, often by deciding who should own a decision. If they delegate, they also need to own the result. Good managers create conditions where people can try things, fail honestly, and surface bad news fast without feeling watched or punished at every turn.
Practical Steps
- Build an "everyday risk" habit. Pick one small uncomfortable action each day: ask the question, give the feedback, say no, admit you are struggling, or share an unfinished idea.
- Treat fear as data. When you notice yourself thinking "maybe this isn't for me," pause and ask whether that is a real limit or just avoidance.
- Do not have hard conversations at peak emotion. Wait until you can explain what bothered you without making the whole exchange about your anger.
- Before taking a work risk, get specific about the stakes. Ask: What am I afraid will happen? What is the likely downside? What matters more to me long term?
- If you manage people, define success and values clearly. People take better risks when they know what the team is trying to do and how they are expected to work together.
- When an experiment fails, review it fast. Say what you expected, what happened, and what you learned. Make that normal.
Notable Quotes
- "The price of confidence is that you have to do things that you are scared of." - Julie Zhu
- "It doesn't have to be the big things... Sometimes it can be these little everyday things." - Julie Zhu
- "I'd like you to be the person most obsessed with figuring out as quickly as possible that you were wrong." - Julie Zhu
Full Transcript
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That trust is built on scale. Bill has securely processed over a trillion dollars in real transactions supporting teams and handling payables, receivables, and expenses. When financial tasks are organized and visible, it can free up time and energy to focus on what matters most, whether that's your team, your mission, or your community. Visit Bill.com slash proven and get a $250 gift card as a thank you after speaking with a Bill expert. That's Bill.com slash proven. Terms and conditions apply. See offer page for details. 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. So 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 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. 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 recognized 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 had gotten 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. 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 looked 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 are 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. 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 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 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 it's training a muscle, you know, which is also one of the things I'm doing now in my later years. It's like actually getting more athletic and doing more sports and things like that. But yeah, like when I first started, like 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. 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, 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, I do actually, I, 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, I gotta get cool with the discomfort again, you know? I also think Molly, there's such a big difference between the risk that you sign up for or the, 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, right? 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, 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. This episode is brought to you by LinkedIn. Running a small business means every hire matters. A bad hire can cost you time, money, and momentum. A good hire, they can change everything. 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That means reliable uptime, easy switching, smart communications. Powered by AT&T Business. Built to work. Get AT&T Business at business.att.com. One 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 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 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. 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 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 or resources to sift through piles of resumes and find the right fit. That's why LinkedIn built Hiring Pro, your new hiring partner that screens candidates for you, so instead of sorting through applications, you can spend your time talking to candidates and finding your next great hire. With Hiring Pro, you can hire with confidence knowing you're getting the best talent for your business. In fact, LinkedIn found that its users are 24% less likely to need to reopen a role within 12 months compared to the leading competitor. Join the 2.7 million small businesses using LinkedIn to hire. Get started by posting your job for free at linkedin.com slash worklife. Terms and conditions apply. One 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. 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 to make the 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, I think that when it comes to this issue, George on the team has the most context. 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 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 the right thing to do if you truly do know better than everyone else on your team. But at that point, maybe you should be hiring a better team or maybe there's something else that's going on in terms of the structure. That goes back to, I think good management is really about just being very aware and 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 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 scarier, 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. It's 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? 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 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? 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, our company, I want you to feel like you can take that, right? 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. 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 if we feel like there's always going to be an evaluator or judge who is just looking at our every single move. They're just, it doesn't, 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 there, right? 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 hired people to do is like, um, is just to go and, and do their best work and use all that talent and skill and brainpower 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, 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. 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 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'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? Like, 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, we're like, what does success look like for my life? Like 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, right? 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