Transcript, E123: Reopening: Sukhinder Singh Cassidy on how to take risks again

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For more on this episode of Hello Monday, check out this article on my conversation with Sukhinder, and leave your thoughts in the comments.

This episode of Hello Monday, "Reopening: Sukhinder Singh Cassidy on how to take risks again," was first released on August 16, 2021.

Jessi Hempel: From the news team at LinkedIn, I'm Jessi Hempel, and this is Hello Monday. This week is the final episode of our REOPENING series. We've taken a deep look into what we want from our work lives as we finish quarantine. I think it's clear that we've all changed. The last 16 months, they've changed us. Now as things open up again, we want to approach our careers with ambition and optimism. Now we've talked together about where work happens, and who we work with. We've examined our habits, good and bad. We've processed loss together, and we've gotten in touch with our dreams. Today we tackle our sixth and final big question: How do we take risks again? 

This episode's meant to be pragmatic, and so I've invited Sukhinder Singh Cassidy to join us. Sukhinder came up in Silicon Valley, and I've followed her career and known her as a tech executive ever since she was at Google more than a decade ago. And she has a new book. It's called Choose Possibility: How to Master Risk and Thrive. Sukhinder breaks down different types of risk. She offers a strategy for how to build your risk-taking muscle by starting small and acting frequently. She gets real about failure and how to recover from it, and she talks openly about her own failures. And Sukhinder lays out a plan for how to make risks feel safer. Here's Sukhinder:

Sukhinder Singh Cassidy: Well, let's talk about risk is and isn't. And I think it's very fair to say that the pandemic has given us a whole new kind of perspective on risk. But historically, if you look at the Merriam-Webster dictionary, risk is something that can cause you injury or harm. So like, there's a challenging kind of connotation around risk that automatically has us thinking about the downside. Interestingly, risk-taking is a far more balanced definition. If you were to look at the dictionary, it talks about uncertainty on the way to a goal. And I think that that's probably how we're all talking about risk taking in this conversation.

I want to put one more important caveat on it because we have all lived through something that researchers call a "coconut experience of risk." Turns out that there are subways and coconuts when it comes to risk. Subways are, you know, things in your life that have volatility, right? But you can anticipate the volatility. So if I said to you, "You're taking a subway-type risk," it's the risk associated with, like, what time is the subway going to arrive at the local station? It can arrive between 7:58 and 8:03, but you know that. You can anticipate that. And so you can plan for it, right? You can do all the thoughtful planning, so "I'm going to arrive a minute early. I'm going to cut it close, but I know the risk I'm taking." And those things happen a lot.

So the question is, how do you become calculated? But then we have what's called coconut risks. Coconut risks are, literally, the risk that a coconut drops out of a tree, hits your head and kills you. And we think that those risks never happen. And oh my God, we just had one, right? We had a coconut event in our lifetimes.

And so I think when we think about what risk is and isn't, coming all the way back to the beginning, risk is something that we often associate with harm. But for the most part, in our careers, we have opportunity to take risks for upside and for growth. And that's the important thing to remember. It's always in pursuit of an end goal (laughs). You know, we deal with subway risks, which are risks we can anticipate and we want to be smart about them. And then we deal with coconut risk. And while we think that coconut risk is brutal, and it is, coconut risks do teach us something about our resiliency. And you'd say, "Well, we didn't take any risks, Sukhinder, over the past year." And I would argue that we did because all of us, in our day jobs, had to show incredible agility to just have our businesses survive. Does that make sense?

Jessi Hempel: Completely.

Sukhinder Singh Cassidy: ...And personally survive. So weirdly, we did become risk-takers in responding to this massive uncertainty and risk from our environment. We all weirdly had to take a lot of risks just to make it through. And so just understand that when massive risk shows up in your life, you're forced to respond anyway. So it's a better time than ever to think about what does risk-taking mean for you? Because even though you think you can avoid it, you can't. And so the question is, how do you embrace it? Particularly when you have these moments where, like you said, the pandemic's not over but work is opening back up. So this is an opportune time to reflect. And then think about how do you want to use risk to your advantage?

Jessi Hempel: Yeah and to figure out where the opportunities are to take chances again.

Sukhinder Singh Cassidy: You got it. Where do you take chances again? And you may say, "I don't want to take any chances at all 'cause I was forced to take a lot of chances this past year." And I would say, "Yes but you learned something about yourself." By the way, you would probably also put risk in perspective. Think about that. Think about the risk that just got put in perspective.

Jessi Hempel:  So you can't talk about risk without talking about failure. And I just want to take a step back on failure because, you know, I wrote about Silicon Valley for decades. You worked in Silicon Valley, and failure is ostensibly a badge of honor, at least people say it is in the Valley. You got to fail a lot. You got to fail often. And so few years ago, I thought "I'm going to make a podcast. It's going to be all about people's failures. We're going to dissect people's failures." So I went to all my sources and I was like, "Let's talk. I know this company worked, but let's talk about that other one that didn't." And they all said, "No." They said, "That it is awful. It is painful. I don't want to talk about it. I don't want to acknowledge it. We can't- I-I can't talk about that." And it speaks to the sort of double standard we have around embracing failure. And I'm curious how you think about that.

Sukhinder Singh Cassidy: Yeah, well first of all, I think you've pointed to two things that are both true, right? Number one, people say failure is feedback. Of course, the book tackles the idea that failure is a feedback loop, and you can only choose your next possibility with information. That's why the book is called Choose Possibility, 'cause we're always in the process of choosing the next possibility. You don't choose once, you choose many times. So it's absolutely true that failure is feedback, and it's hard to succeed without it. But to your point, you know, everybody brags about their startup failure in the Valley because, in hindsight, you can talk about it. In the moment when that failure is happening and it's big, it is so brutal. And if you ask people to dissect it, you're right, like everyone wants to talk about when it's way in the rear-view mirror. And, you know, I can equate. I think you know this story about me, but I go into it in more detail than I've ever done in my life in the book...

Jessi Hempel: Yeah.

Sukhinder Singh Cassidy: ...Which is, you know, my first CEO job was a failure. Like it was a failure if you measured it, you know, and I do measure it like as an absolute standard. That I was in and out of a job in six months after having given up an enormous career at Google. And I did all the right things in calculating the risk I took in going to a startup, in the industry, in the team, in like my ability and my strengths relative to the team. And to be honest, six months later, the founder and I both wanted to run the company differently, and the board chose him. And it was, to your point, excruciating. If you'd asked me to talk about it then, I would say, "No effing way." I disappeared to ski with my family 'cause I just didn't want to see anybody. And oh my God, if somebody had like met me at a cocktail party and they, you know that classic question, "What are you doing now?" And you have to explain what you're going through when it's still pretty raw. It's-it's brutal. 

But I think to your point on dissecting failure, yes I can do it now in hindsight because it's seven years since. But the more relevant point I think is, when we look back on our failures, we want to know a few things. A. What led to them. B. The thing that people don't understand about failure is, it's often when we're pursuing reward. We think of it as one reward. So I'd say, "Well, probably what was a failure for me as a CEO, true." But if I took, if I dissected that decision, I'd say, "Well actually, I made four decisions at once. I made the decision to leave Google, OK? I made the decision to enter the e-commerce industry. You know, I made the decision to become a CEO, and I made the decision to join Polyvore." In hindsight, I feel really good about three of those four decisions because in fact, they did set up the pathway for me to ultimately, you know, become an e-commerce investor, entrepreneur again, board member and run StubHub. I can say I've loved the joy of being a CEO. Like that's something Google could never give me. 

So I think that what's important about failure is a- I think the value for other people is not just glossing it over and talking about it when it's cool to talk about it 10 years down the road where you could say, "Look at me. I'm a success now." 'Cause yes, inevitably, you will come back to a cycle of success. But I think it is about, in my mind, looking at the unpacking the decision and saying, "OK, I didn't make one decision, I made four. Let me evaluate each of those decisions." And so for me, what was helpful about looking at that failure -- once I could talk about it without crying -- was OK, which of those decisions that I made would I judge now to have been sound, or not sound, have worked out in a way that I'm happy with 10 years later through multiple cycles, by the way.

That's what's the risk with failure. That people throw out everything. The baby with the bath water, does that make sense? They look at it and they say, "Oh my God, I failed." And then they retrench all the way, and I'm like, "OK, stop for a moment, unpack." (laughs) “Figure out which parts to keep and which parts to let go of."

Jessi Hempel: I appreciated how open you were about your experience at Polyvore. I mean, in part, I remember writing about it. How long did it take you to digest that personally and take from it the aspects that could drive you forward?

Sukhinder Singh Cassidy: I would say probably a good three years, and keep in mind, like you want to take that failure. Remember I started one of the first video-commerce plays in 2010, and we sold Joyus for a small number in 2017 'cause we couldn't get the unit economics to work. And right now that same company would be worth, I don't know, you tell me. You know what video-commerce companies are pricing at right now in Series Bs. So I mean, I didn't just have one failure. I had two, effectively, in a row. But I would say, on average, a really painful failure for me, it's probably 12 to 24 months before I can talk about it without tearing up. I mean, big ones. That doesn't mean I don't talk about them, but like me literally without feeling somewhat emotional. And it's probably two to three years before I fully let go of something. And I don't know if people admit that, right? I mean, it's like big failures, they hurt.

Jessi Hempel: Well, here's why I asked that question. And this is perspective that comes from being fully in the middle of my career. No longer at the beginning of my career. And I'm curious if it's perspective you share. There's so much value in taking the long view in your career. And in the moment of any failure, and even in the moments leading up to and post any failure, it can be so easy to be locked into the current moment and so focused on it. But any more you understand, like the significance of stepping back and looking at the long arc of your life, as you evaluate the risks to take going forward.

Sukhinder Singh Cassidy: Absolutely, but you hit the one thing, right? Early in our careers, if you haven't lived a cycle. And by the way, this is not like, "Oh, I'm so wise." This is just like, "I'm old."

(laughing)

Jessi Hempel: I wish I were wise. (laughs)

Sukhinder Singh Cassidy: ... But-but you understand. Like how can you have faith in a cycle if you've never seen a cycle, right? So once you've lived two or three cycles, even though it's still incredibly painful. And in some regard, it's ironic that when we- we have more, we fear more what we'll lose, right? Like even though those things are true, once you've lived one or two cycles, then you at least have confidence that there will be a recovery. You sort of know, if I could just like live this through.

But I think when you're young, and I was the same when I was young, every failure I was just like, "This is it. I'm done." You know (laughs) and then you're not done. And you ride your way through that curve. And so, I would just say small failures for me, yes, it's easier for me to recover now. Like if I take a risk today and somebody says I'm an idiot, whatever. Like somebody listens to this podcast and is like, "Oh wow, what a joke. Like Sukhinder wrote a book, and like what does she think she knows?" I'm like, "OK, that's a small failure." Like whatever, I can recover. But on big failures, of course it's still painful. And I don't think that goes away. I think all that happens is you just kind of persist through a cycle, and you kind of have more confidence on the other end. Everything will reform and reshape over the next three to five years. So yeah, but you have to be able to give at that time. You can't really just say, "I'm over it. It's going to be good in, you know, 12 months. Maybe not."(laughing)

Jessi Hempel: Maybe not and that's the lesson the quarantine gave us, which is like, it may not be good in three months more but just stay in the game.

Sukhinder Singh Cassidy:I think that's the key. And even before, I think on a failure, it may be like, take a pause, take a beat. You want to hide. You want to binge watch TV. You want to eat food. You want to not exercise. You want to not talk to anybody for four months. Go ahead, you know, and then get back in the game. Take what you need to recover, you know what I mean? You don't want to see people who are going to bring down your energy or ask you a question you don't want to answer, don't. Like that's perfectly OK. Whatever it takes for you to stay in the game, you stay in the game.

Jessi Hempel: Well so, I want to talk about why people take risks, and there are different reasons that people take risks...

Sukhinder Singh Cassidy: Mmm-hmm.

Jessi Hempel: ...And like one big reason that a lot of people are taking risks right now is, you quote Anaïs Nin. It's one of my favorite quotes in your book. "And the day came when the risk to remain tight in a bud was more painful than the risk it took to blossom." And I love that sentiment because for a lot of people, risk necessarily comes back when the thing that you were doing is just not working, and that pain is so great that the pain of doing something new is smaller. That's one big reason why people take risks.

Sukhinder Singh Cassidy: It's true, but this is the irony, right? And you hit it. When something gets so painful that like you can't endure the thought of greater harm, you actually take a risk to change it, right? So when the downside is like already bad and getting worse, we actually have more courage to change than when things are good, right? When things are good, we often overthink this idea of taking a risk. So it is one of the biggest ironies that, you know, avoiding further harm is one of the biggest reasons we actually move ourselves.

Jessi Hempel: We're going to take a quick break here. When we come back, Sukhinder will tell us how we can be more proactive instead of reactive.

(podcast ad break)

And we're back. Now as we've heard, a lot of people wait until they have no choice to take risks. They're literally forced into it. The price of doing nothing is suddenly higher than the price of choosing to do something. But I want to encourage people who aren't necessarily in pain to be more ambitious. To think more broadly about taking chances and about what they might love to do. And so I asked Sukhinder, well, where does the impetus to do that come from?

Sukhinder Singh Cassidy: Well, I think you're hitting what we call risk-taking for upside, which is the reason most of us should take risks. First of all, I don't think people lack ambition. I think what they suffer from more is this idea that one single choice has to be perfect. So I think they succumb to what I would call "the myth of the single choice." I think everybody wakes up every day thinking about what they would do differently to be happier, richer, you know, more personally fulfilled, feel better about themselves, all of those things. But I think we have set up people to believe that the world's biggest risk-takers take one mighty risk, and they fail or succeed on the size of the risk they take. When in fact, dissecting most people's career, you'll find that they have risk as a muscle. And risk as a muscle means you have to, by defacto, do it frequently. And it's OK, it doesn't even matter the size of the oscillation, you know what I mean? 

Big risk, it's more frequency of risks. So I would say to people, "OK, if you want to move towards your ambitions, why don't you take small risks today to either discover, learn or to pursue like the minimum viable step towards an ambition?" So let's say you want to be a startup CEO, and I'm like, "OK, but you're in a big company today." Like those are many leaps away, right? So you can say like, "Gosh, I'm just getting one idea and take one giant leap." And I'd be like, "OK, well you can also make a move today to discover what being a startup CEO is like." You could literally read 10 interviews. You could go sit in an incubator and like watch what the mechanics of your startup are. You could go, you know, moonlight with your friend who happens to be at a startup, even if they're not the CEO. 

Like I could name 10 little risks you could take today, but if instead you're like, "Well, that leap is too big. So I choose nothing because that leap is so big, I might just fail." And I'm like, "Yeah, when looked at that way, if it's just binary and one big choice, I wouldn't take any risks either." (laughs) But if I broke it down and said, "How about you take risk to discover, take risks to learn, take risk to achieve an ambition, but micro size it." I would tell you that frequency matters far more than size of oscillation in the risk you take.

Jessi Hempel: I love thinking about risk as a muscle, and you need to exercise and flex that muscle.

Sukhinder Singh Cassidy: Exactly. I'm like, come on, all the world's best risk-takers, like they're on risk number 10,000. Could be risk 1,000, you get the point. (laughs)

Jessi Hempel: You know, it also strikes me, look, there's a hierarchy to risk to who gets to take risk.

Sukhinder Singh Cassidy: Yes.

Jessi Hempel: Right?

Sukhinder Singh Cassidy: Mmm-hmm.

Jessi Hempel: And you are a woman of color.

Sukhinder Singh Cassidy: Mmm-hmm.

Jessi Hempel: Does that shift the amount of risk you get to take? How do you think about that?

Sukhinder Singh Cassidy: First of all, I think that is a really critical question because I think it's very easy to say to people, "Hey, take more risk." You have to ask the question, "Are you in an environment where it's safe to take risk?" So let's just step back and say, "OK, as a woman and person of color, can I take risk?" Yes. Part of the reason I can take risk is because I have saved wealth, and I have achieved a certain amount of career capital where if I fail twice, I have enough body of work. And, you know, I've played the law of probabilities in my career, and I have enough successes to be able to withstand the failure at this point. One might also say that I've had a lot of practice, so I take more.

But coming back to this question of can people take risks equally? I come from a worldview where I believe possibility is abundant. It's not that if you get some, I get less. But I believe the possibility can be unevenly distributed if you're in a system where risk-taking is risky. And what I mean by that is, are you in a place where your values fit? Where like who you are and how you operate in the world is simpatico with that environment that you're in. Because I think when we go into environments where what I say is a little risk, "Hey, speak up, be a truth teller." OK, I can say that, but if the cost of being a truth teller is. You know, everything you've seen practiced by the organization is that if you're a truth teller, like authenticity is not valued even when done productively, then it may be unsafe for you to take that risk. So I don't think we can blanket all women and all people of color have less opportunity to take risk. What we can say is, there are environments in which possibility is unevenly distributed because of, let's call it, preconceived notions and bias.

Like a successful person looks like this, so that, you know, impinges some constraints. And then I think it's really about values fit and being in environments where we are included, and we feel safe to take risks that are consistent with who we are as individuals. And it's absolutely true that when you operate in systems of bias, right, if there is values fit with the underlying leadership of the organization, I still think it's possible to thrive. Because every, every company we know has bias of one kind or another, and every one of us as individuals. But, you know, I've met people who have biases just like I do. But if I feel like our underlying values system is we both value transparency, we both value authenticity, we both value self-learning, then I'm OK to take a risk and say, you know, "This is what I experienced here, and this is how I think it could be better." So we're all in systems of bias, but values fit is key.

Jessi Hempel: Well, what you said right at the beginning of that thought was I created enough wealth that I was gonna be OK if things didn't work out. And I thought about the way that we de-risk risk so that we can actually take chances...

Sukhinder Singh Cassidy:  Take more. (laughs)

Jessi Hempel: ...And I remember I had the CEO of Zoox, amazing woman, Aicha Evans on the show a while ago. And she was talking about how before she took the leap and became the CEO of a startup, she spent a good, long time under the umbrella of a large corporate, building the wealth that was going to give her the platform to take the risk without being fearful that she wasn't going to able to support her family.

Sukhinder Singh Cassidy: Absolutely, right? When we say take risks, this is another myth. I think that calculated risk-taking is the opposite of being rash. It doesn't mean you don't make a big decision or life-changing decision, but it's calculated. I mean, I want the world to become calculated risk-takers. And I'm the same. Like I always had a view of risk diversification as well as focus, right? So like you can't succeed if you're just overly diversified, but you can think about diversification of risk when you know you're taking one major one. You're like, "OK, what am I going to do to offset that?"

Jessi Hempel: It reminds me of a guy that I wrote about once who is a very successful founder of a tech company. And he had as his hobby he liked to walk on plane wings.

Sukhinder Singh Cassidy: What?

Jessi Hempel: ...Yeah, that's exactly the response that I had. (laughs) You, you, what? I was like, "You run a company that is so large, it just seems really irresponsible of you to be walking on the wings of planes." And he said to me, "Actually, this is the least risky thing I do because in order to get myself to the point where I can walk out on the wing, I have to have such a background in everything from the makeup of the plane, to my ability to do it, to my equipment being safe." Basically his point was, I have done so much in advance of getting myself to this place that this one step...

Sukhinder Singh Cassidy:Yes.

Jessi Hempel: ...that I take is the smallest risk...

Sukhinder Singh Cassidy: Mmm-hmm.

Jessi Hempel: ...In this sort of larger equation of risk here. And I know that sounds a little absurd, but I think the metaphor is right. That things that seem really big are actually just a collection of little tiny choices stacked up against each other.

Sukhinder Singh Cassidy: You got it, and I think that is the way risk really unfolds. It's not binary. You don't go from zero to 1,000 miles an hour. You basically are unfolding a series of choices. And by the end, you may have pivoted or you might have taken one gigantic leap for mankind, but you might've walked a mile or you might've walked 500 feet. It doesn't really matter. What matters is the process of iteration, right? And it's always a collection of risks, which is why I say to people like, "You're so busy over-weighting the first choice as if it's the only choice you'll make." If I were to tell you that between you and any reward that's gonna happen, it's gonna be an accumulation of choices, then you just worry about getting an emotion. 'Cause what we really want to do, right, is keep unfolding to the next choice. But unfortunately, most people are stuck at the first choice because they think it is the determining factor. (laughs) I'm like, uh it's not. It's just not, like stop worrying about the first choice. Worry about getting an emotion and having the ability to make 10 choices or 100. And take some relief from that. When we think it's just one mighty swing and that's all we get, um, I think that is like, it's a very pressure-filled way to think about taking risks in our lives. And I'm not surprised people then do nothing. They choose stasis.

Jessi Hempel: There's one other thing I want to explore with you before we finish and that is ... It was so obvious reading your book, it's obvious knowing you, that one of your superpowers throughout your career has been to connect broadly to lots of different kinds of people and build relationships with them and nurture those relationships over time. And I wonder the degree to which that social network and the way that you have tended it, created the opportunity for you to take risks. Because the fact that you've been able to build this community over the course of your career, insulates you from falls that otherwise might happen, in an interesting way. And I want to encourage our listeners to also give the kind of care to their relationships with colleagues, customers, people they work with, people in their industry, that you've given to yours because I actually think that's part of the risk equation.

Sukhinder Singh Cassidy: I think you're making two important points. So number one is, whenever I've taken a risk ... people always say to me, "How's your career unfolded?" And I've said, "Look, I do great work for great people." And I've put the 'who' above the 'what.' And when I've thrived, it's because I put myself in the company of people I admire, respect, could teach me something, who share my values but are very complimentary to me. Like bosses who let me run, and people who basically accepted my strengths and my gifts and didn't maybe try and like direct my productivity and energy but not like shut it down, right? And so, I've had the value of that in my career. Now, I think you're making a slightly different point. 

So first of all, when you take risks, you know, put the 'who' in front of the 'what.' But I think the converse is true, like once somebody has taken a bet on you, in any dimension, your job is to do right by them. And for me doing right by them, it doesn't mean you're always going to win but it means they're coming to you with a promise of like who you are and how you show up. And for me, it's been very important. My whole career I'm like, "Yeah, show up authentically." I show pretty imperfectly 'cause if you work with me within a minute you're gonna understand I'm impatient, I'm intense, I can be vastly irritating. Like all those things are true, but mostly I want to show up with some confidence that I am going to be here, and I'm going to care and we're going to get it done -- drive. And then I'm going to show up with some level of humility and be like, "Look, I can't promise you the outcome. What I can promise you is the journey will be filled with these things, and these are my values. And if that's good with you, we're going to be good, regardless of what happens here." 

And so, I'd like to think that I've shown up consistently with my values, with all the people who've worked with me. If you want to go through the world and burn a lot of bridges, like the world already has enough about volatility. If you want to include in that volatility, like pissing off enormous numbers of people by being a jerk in how you work with them, knock yourself out. But to your point, the next time you take a risk, don't expect them all to stand there and cheer for you in the corners or like step in to help when you really need it. 'Cause people will treat you the way you treat them 'cause we all need each other, right, to deliver. So there's no way I'm delivering on any risks I've taken by myself, it's just not happening. (laughs)

Jessi Hempel: That was Sukhinder Singh Cassidy. Her new book is called Choose Possibility. Thank you, thank you, thank you for joining us for the REOPENING series. And if you've missed any of our big questions, now's your chance to go back and take a listen. 

You can find the first five episodes anywhere you listen to podcasts. I think that this moment, this one now, it offers a turning point for a lot of us. The pandemic isn't anywhere close to over, but a year and a half in, we are growing. We're learning to live differently because of it. We're coming out of hibernation. And now is our opportunity to step into ambition again. Just as we've always done Hello Monday, myself, our producer Sarah Storm, our contributor Michaela Greer and the entire team who bring you the show, we're gonna continue to explore the changing nature of work, and how that work is changing us. So what do you want to hear about next? What matters to you? Email us at hellomonday@linkedin.com and let us know. 

Hello Monday is a production of LinkedIn. The show is produced by Sarah Storm with help from Taisha Henry. Joe DiGiorgi mixed our show. Florencia Iriondo is head of original audio and video. Dave Pond is our technical director, Michaela Greer and Victoria Taylor distinguished themselves as risk-takers. Our music was composed just for us by the Mysterious Breakmaster Cylinder. Dan Roth is the editor-in-chief of LinkedIn. I'm Jessi Hempel. We're back next Monday, thanks for listening.