Why Playing It Safe Might Be the Riskiest Thing You Do ft. LinkedIn's Aneesh Raman

Hinzugefügt: 2026-06-03

[00:00:00]And welcome back to day [music] two of our series on Open to Work. Your New York Times best-selling book, how did you feel when it was on the best-seller list? Relief, I think. Cuz we weren't sure how it was going to land and if anyone wanted to read it and if the message would resonate, so I think it was oh, this was worth it is what it felt like.

[00:00:16]>> Well, I think it's a brilliant book. I also think for all of the Squiggly Career listeners, it's a real companion to Squiggly Careers because like this is why you have to develop the skills cuz this is what's happening at work every day.

[00:00:26]>> is partly why we wrote it and you're called out in this book and so many sort of early thinkers about how we should change work and careers are in the book.

[00:00:34]We wanted to take all of that and all that you've been doing for years now and give it this bigger frame, this complete disruption to work. I think the greatest disruption to work in human history backed by LinkedIn as a point of view that people will believe that feels credible because we've got more than a billion members. We're in 200 countries and territories. So, we're so thankful and grateful for the work that so many of you have done to tee up how we should approach this and felt like our role was to sum all that up into this big moment so that people could like pull from it.

[00:01:03]And she is a super quotable book. Like I I was like highlighting and I was like that's a great point, that's a great point. I've got so many points in there.

[00:01:10]I really like there's a quote in here that says like even if you're not changing jobs, your job is changing. And I that's such an important point cuz I think some people might think oh well, there's no I'm in my job, I'm happy.

[00:01:21]It's like no, that this change is happening to you.

[00:01:23]>> what's interesting I hadn't thought about it till now is that you may be in a squiggly line career in ways you don't realize in the job that you're in without changing that job title. Take software engineers right now, their job is fundamentally changing from largely coding to now things like talking to customers, thinking about ethical implications of what they build. That's like changing your job even if you're not changing jobs into a new job. So, there's going to be squiggly line careers happening even for people who don't change jobs or job titles. It's constant. So, so that links to me to the skill that we're going to face on stage, which is all about courage, which I think of the five, I was like, "Oh, this is the hard one." And I was like, "There's a whole context that sits around courage." So, tell me why you felt that this was necessary to be one of the five capabilities that helps people get ahead in the age of AI. I mean, again, we were looking across human history at what has made us us and what has led to everything up to including an AI, but going back to nation-states, to civilizations, to the monetary order, all the things humans have done before the industrial age. And courage is just so central to that. I mean, we talk about it in the book, exploration, which defined the human, you know, humanity for a period of time just to explore the world. We talk about the Polynesian wayfarers just going into the ocean, into the unknown, not knowing if they'd come back, what would be out there, and finding places where they seeded cultures that exist still today. We open with Apollo 13. Think about what astronauts do, the courage it takes to go out, you know, beyond our atmosphere for the sake of humanity and our understanding of the world. So, actually, like curiosity has fed courage because courage is necessary to feed curiosity as we wanted to know more, but courage is so instrumental in how we've done anything as humans. And so, we felt like that had to be a key part of it.

[00:03:10]And I was thinking there about like careers, which can often feel quite unknown. But, you know, you need the courage because people are feeling uncertain and there isn't this ladder-like predictability anymore and people don't know what's coming what's coming next. But, I was also thinking that to to Which, by the way, I think part of what gave you cause to talk about Squiggly Line is for a long time at work, you were told not to be courageous, but to be compliant. And so, it's going to take courage to be courageous right now because it is so different than how the world of work has worked today.

[00:03:39]>> Yeah, and and then in the book, you talk about it it sort of turns hesitation into action. And I was I was thinking it's both it is both a human skill to develop, but it was also in the context of an environment that supports it.

[00:03:52]Like, those two things have to go together or you have these like courageous individuals that get knocked back in companies.

[00:03:58]>> Which I mean a lot of my career has been that across the sectors I've been in from media to politics to tech. It has been me trying to push something new, me trying to try something new in environments that have generally been about compliance. Like no, we're not looking for individuals to do something new. We're looking for you to fit a job description, to fit a job category, to fit a functional set of responsibilities.

[00:04:22]And so the environment has to be there and and the easiest way to understand it I think for companies is you have to give permission for failure. Because courage is a willingness to act despite the possibilities of failure, whatever that gets defined as.

[00:04:36]And if you're in an environment that disallows failure, that is going to stifle innovation, it is going to stifle growth, it is going to stifle and suffocate your company over time. But building around an allowance of failure is a completely new way of work and that's got to happen around individuals. One of the important things we did with the book which was written for individual workers is as we get through the chapters about how to think about your job, how to think about your career, the end of the career chapter says, "And we have to acknowledge something important.

[00:05:06]There's only so much we can do individually. You can follow all our advice, your advice. We can all do the right things individually, but if we aren't in companies that are adapting, if we aren't in economies that are adapting, there's only so much we can do individually. So this is a call to action not just for individuals, but for companies and for policy makers as well." So I'm going to come back to the individuals, but I just want to share cuz I I totally support what you're doing and we found exactly the same with Squiggly Careers. It's not It's not just about the individual developing the squiggly skills. You have to work somewhere that supports a squiggly structure so people can squiggle and say you've got to have both. Uh so what we do in case it's helpful to anybody listening for the the that kind of how do you create an environment where failure is okay? Um we have mistake moments.

[00:05:46]Um >> so we have a we use Microsoft Teams and we have a channel on Teams and when people make a mistake, the rule is within 24 hours you have to share it.

[00:05:54]And people take a deep breath and like I had one I saw one of my first in my team yesterday who did this and I know it was a deep breath moment. And you share the mistake, you share what it was, why it happened, and what you've learned. And it kind of it it gets the weight of the mistake out, but what comes back is a whole lot of shared learning and a lot of support.

[00:06:12]>> Yeah. And I think creating that environment where someone can be courageous to do something they might not have done before. And if it doesn't work, you can share it, you don't have to be weighed down by a mistake and we we move on and learn from it.

[00:06:23]>> Well, and if you're doing something courageous, failure is inevitable. I mean, nothing great has happened without going through failure. And and courage is necessary because you're going to go through failure. So, if you aren't failing, you aren't doing in this new world of work. And to fail is to be courageous because we have asked everyone to not be allowing of failure. And I think that that is a great way to frame it. I mean, there're different versions I've used.

[00:06:47]There was a period I went deep in philosophy as part of the research for the book. And Marcus Aurelius has this great line of the obstacle is the way.

[00:06:55]Like you only going to learn through the failure. Like the the how to handle hard well, all the the sort of work that's out there on that. And then with my girls, we have a 9-year-old and 11-year-old, I'm so thankful social emotional learning is now part of early childhood education, emotional regulation, problem-solving. We talk about great mistakes.

[00:07:13]And how you can make a mistake, but it's great because you learn something. Or for next time there's a new way to go at it. But if you like lose your retainer twice, that went from great mistake of we learned that you got to do this to okay, we've made the mistake twice.

[00:07:26]Usually the second time isn't great.

[00:07:27]It's our reminder [laughter] that you didn't do the thing you were going to change. I am I also have a 9-year-old and 11-year-old. I might I might adopt that. But and in work sense, I also really look to the work of Amy Edmondson who kind of differentiates different types like like avoidable failures versus intelligent failures. And I think it's a really it's an interesting topic for teams to talk about. So, if someone individually is listening and they're thinking, "Okay, I would like to I'd like to bring a bit more of courage to my to my career to my work." What would your advice be?

[00:07:54]>> You know, so I think with something like courage, start small. I mean, the great thing about the human brain, which is the most amazing object in the known universe, uh human intelligence, not artificial intelligence, is why everything, including artificial intelligence, exists around us and why I am so excited about where work is going cuz the mind, not the machine, will be at the center of work. Um we are able with neuroplasticity to literally rewire our brain around new habits, new beliefs, new stories, including of self. And the way we do that is through deliberate practice every day in small steps. I just finished a few books called Tiny Experiments and Little Bets. Tiny Experiments is about literally how to rewire your brain, the neuroscience of like habit changing. And then Little Bets is about how all innovation starts with little bets. So, courage can sound really intimidating. And I think if you overdo it and just go flame throwing into like a meeting and say blow it all up, like it could backfire.

[00:08:50]You don't want to do that. You don't need to do that. You'll get to the giant leap through the small steps. So, it's micro courage. You're going to build in these micro ways. You're going to push on something in a way you wouldn't have otherwise. Like, challenge a conversation in a meeting where otherwise you might have felt uncomfortable. You're going to ask for a conversation or for a coffee with someone that otherwise you were sort of holding back. You didn't think it was something that you could ask for. Just find these small ways in small ways to be more courageous. It's like micro resiliency that you're building. And over time that compounds and you start to get a positive feedback loop over time because you start realizing, "Oh, because I asked that question, the conversation changed. Because I asked for that meeting, I now have a new peer or a new mentor." And so then that's going to encourage you to take more of those steps and to turn those steps into bigger leaps.

[00:09:38]Um I've done both. I mean, I've had moments of small courage, especially with parenting, where you don't want to over-correct in any direction, so you're trying a different way as your kid gets older. I mean, each age is a totally different map that you're trying to um understand. And my wife and I were just talking yesterday about like our 11-year-old and middle school and what do we have to course-correct and how do we want to do it and how do you do it in small ways to test? And then I've had moments of big leaps. I mean, when I left CNN, I was probably our most known international correspondent in the Middle East.

[00:10:11]And I left that entire career to be an unpaid intern on an Obama presidential campaign, where he hadn't won the presidential nomination of the Democratic Party, let alone the presidency. So many reasons that that could have gone wrong. So many reasons I shouldn't have done it. Uh for financial security reasons, career stability reasons, but I had built up enough belief that I had to go be part of that, that it was actually the easiest thing I'd ever done.

[00:10:35]So you'll build to big moments and you want to have some big moments of great courage, some big moments of big leaps.

[00:10:40]You want to just live life. That is life at its fullest is just this I'm going to try something completely new or I'm going to start over in some new way. I firmly believe that we get to reveal ourselves to ourselves most fully through those big challenges cuz that's when you realize like what you've got in you and what you're capable of that's beyond anything you could That only happens through courage. It only happens in challenge.

[00:11:02]But you don't have to do that often.

[00:11:04]Writing a book was really courageous and really hard. I'm not doing another one >> [laughter] >> anytime soon. I'm going back to the small steps.

[00:11:11]So we'll end today with that advice. So look for more moments of micro courage in your week.

[00:11:16]>> Find something that you're going to do tomorrow that feels uncomfortable for you to think about today, but feels doable to do tomorrow. Okay. Literally, I'm going to ask one question in this meeting that I usually don't talk in or that I don't say the thing I believe or I'm going to reach out to one person that I otherwise wouldn't feel comfortable doing it.

[00:11:35]It should make you feel uncomfortable today as you think about it, but it should feel something like you could hold yourself accountable day after tomorrow that you did it tomorrow.

[00:11:43]>> Okay. And on the accountable, I'm going to put an offer out to our listeners that they can email We'll be their accountability partners. They can email us Helen and Sarah at squigglycareers.com. And if they need an accountability partner, they can share what that moment of courage is going to be. Which that itself might be the act of courage. Because if they email you, they know they're accountable for it.

[00:11:59]>> Yeah. But I guess it can't be like, "I'm going to email you that I'm going to email you." Because then they're done.

[00:12:03][laughter] I can you say much for day two? I can't wait for day three. All right.