Sukhinder Singh Cassidy, Author of ‘Choose Possibility’, joins Yahoo Finance to discuss navigating business amid covid and the importance of risk-taking.

Video Transcript

- --want to have a different-- a conversation on a different take on risk. And for that, I want to bring in our next guest, Sukhinder Singh Cassidy. She is the author of the new book, "Choose Possibility." She has built and scaled companies. She was formerly the president of StubHub and has been with a number of huge names in Silicon Valley.

Sukhinder, great to have you. And I mentioned risk. I was listening to the audiobook of your new book, "Choose Possibility." And the big theme, of course, is that risk is not what you think it is. Help our viewers understand your own take on risk.

SUKHINDER SINGH CASSIDY: Well, first of all, thank you for having me. It's delightful to be here. I think when we think about risk, I think for most folks, particularly in their careers specifically, which is really what "Chose Possibility" is about, we think of risk as being a single-choice metaphor. What I mean by that is people subscribe to the myth of the single choice.

And if you look at the things that are celebrated in the media, the celebrities, the influencers, we tend to think that risk taking is for the most risky, and it requires one mighty leap, when, in reality, we ought to treat our careers the same way we do companies in Silicon Valley, which is iterative feedback loops in which we get the compounding benefits.

But it's not about a single choice. It's about a hundred or a thousand between risk and reward. And so it's about embracing that muscle and really building that muscle.

BRIAN CHEUNG: Hey, it's Brian here. Now, risk-taking implies that you might be doing things sometimes that also end up just being mistakes. So tell us about how your book approaches mistakes that you've experienced in the many different types of careers that you've been in along the way and then, more importantly, how to look back on those and get lessons learned from what may have been a mistake.

SUKHINDER SINGH CASSIDY: Well, first of all, I think you're hitting the quintessential issue that people have with risk-taking, which is sort of we have to confront our fear of failure. And the things I would say to people is, in fact, when you're trying to make a choice and worried about failure, I often advise people to do what Jeff Bezos talks about when he talks about Amazon making decisions based on the idea that most choices are a two-way door.

So I always say to people, if you're afraid of failure, first and foremost, before you make a choice, look through failure. Think about the fail mode of the decision you just made and what are the choices available to you after. What are the choices after the choice?

And to the extent that most decisions we make have many, many choices or options after them, it should help us reduce our fear of failure enough to act. And in the converse is true. When you think about once we fail, how do we recover, I think most people think that failure is about sort of ignoring that and maybe being risk averse.

And I'm like, look, if you want to be a calculated risk taker, it's really about looking in the back-view mirror and saying, OK, of all of the risks I took, how do I calculate the odds of those risks and what happened? And really, that's about is it about the environment you're in, is it about the people you're with, is it about your goal-setting in the first place or who you are? And almost every mistake we've made falls into one of those categories.

And so it's just about identifying those things and creating the feedback loop on which people often tell you that failure's about learning. That's absolutely true, but it's also about diagnosing and then being in a position to take those learnings and make the next choice. But for most people, I think it's on the front end, just diminishing the fear of failure enough to act.

- I have to imagine that the pandemic-- the timing of this book and the pandemic has given a lot of folks clarity. I think we're seeing a lot of trends out there. Maybe some call it the Great Resignation. How are you thinking about some of the bigger, more macro themes out there? Are you seeing more people take risk? Are you hearing stories anecdotally? And as someone who's made some risk in your own life, how do you kind of help someone with that-- giving them that psychological permission to take the risk?

SUKHINDER SINGH CASSIDY: Well, first of all, I think we would all agree the pandemic wall was brutal and continues to create a lot of uncertainty in our lives. It's what we call a coconut event, one in which you can't anticipate it. Or researchers call it a coconut event, but they happen in our lifetime.

I think you and I would agree that what people learned along the way is about their own agility and risk-taking ability in the face of trying to avoid danger. People made very fast and rapid decision that they never thought they were capable of making in order to not just survive, but, in some cases, thrive in the pandemic.

And so I think people learned a lot about their agility that they are taking into this moment. And so as you think forward and why this is such a critical time, you have people who are rethinking what it means to work and how they want to work. And that is, I think you're referring to one of the big choices people are making right now is the Great Resignation. The other is negotiating for the kind of hybrid environments they want to work in and what they need to make it work for family and home, when for the first time organizations have a lot more empathy about what that looks like.

And I think for other people, I think we have to acknowledge, there are some people who are still taking risks just to survive the pandemic. They continue to make choices as the Delta variant extends this-- past where we'd all like it to be. But I think in either case, you're seeing people who've learned their agility and are now taking advantage of the new flexibility of work to make new choices. This is why I think it's a critical time to be-- kind of think about your own risk measures and appetite.

- Sukhinder Singh Cassidy, author of "Choose Possibility," congratulations on the book release, and thank you so much for stopping by Yahoo Finance Live today.