Choose Possibility: Take Risks and Thrive (Even When You Fail)

by Sukhinder Singh Cassidy

Overview

Wall Street Journal bestseller | An indispensable guide to decision-making and risk-taking for anyone who finds themselves afraid of making a wrong choice in their career. This fresh, new approach comes from one of the most highly regarded and well-respected female tech executives in Silicon Valley, who made many wrong choices in her career, but learned how to turn those down moments into successes.

Life is made up of a series of choices. What do you do if one of those choices turns out poorly, especially if it was carefully considered? How do you trust your instinctive decision-making skills and make the next right choice? How do you continue to take risks when, suddenly, your risks are not working out?
 
Sukhinder Singh Cassidy is one of the most highly regarded and well-respected female tech executives in Silicon Valley, but she’ll be the first to admit that her path to success has been far from linear. She started three companies that have done exceedingly well, including theBoardlist (an organization designed to promote and place women onto corporate boards), and she just served as president of StubHub, which sold earlier this year for $4 billion.
 
But she’s also encountered plenty of poor choices, misfires, unexpected headwinds, and all other types of pitfalls that she had to learn how to confront, analyze, navigate, and incorporate into her new path forward. From her own experience, she knows that personal success does not come from making one singular “correct” or “big” decision. Rather, long-range success comes from tackling numerous choices that are aimed to optimize future possibilities.
 
Singh Cassidy’s “seven myths of success,” as well as her advice on how to make FOMO into your friend, multiply your “bets” in life, and understand why you shouldn’t be blinded by “passion bias,” all provide an entirely new way to approach risk-taking and achieve lasting success.

Product Details

ISBN-13:	9780358525899
Publisher:	HarperCollins
Publication date:	08/17/2021
Sold by:	HARPERCOLLINS
Format:	eBook
Pages:	272
File size:	4 MB

About the Author

SUKHINDER SINGH CASSIDY is a leading technology executive and entrepreneur, board member, and investor with twenty-five years of experience founding and helping to scale companies, including Google and Amazon. Most recently, she served as president of StubHub and as a member of eBay’s executive leadership team. She is the founder and chairman of theBoardlist and has been profiled in Fortune, Forbes, the Wall Street Journal, Business Week, and the New York Times, among others. She has been named one of Elle’s Power Women, one of the Most Creative People in Business by Fast Company, and one of the Top 100 People in the Valley by Business Insider, among many other accolades. She lives with her husband and three children in Silicon Valley.  

Table of Contents

Foreword xi

Introduction xv

Part I Get Going

Chapter 1 Ditch the Hero's Journey 3

Chapter 2 Pump Your Risk-Taking Muscles 15

Chapter 3 The Power of Pipelining in Parallel 27

Chapter 4 Why Proximity Beats Planning 39

Chapter 5 FOMO > FOF = ACTION 53

Part II Get Smarter

Chapter 6 Put Who Before What When Taking a Risk 71

Chapter 7 It's Not All About You 86

Chapter 8 Well, Some of It Is (How to Bet on Ourselves) 101

Chapter 9 Bigger Leaps 116

Part III Get Rewarded

Chapter 10 The Myth of Risk and Reward 137

Chapter 11 To Succeed, Forget Success 148

Chapter 12 Impact Fails 172

Chapter 13 The Sines of Growth 192

Chapter 14 Possibility and Powerflow 209

Acknowledgments 222

Notes 226

Index 239

Editorial Reviews

06/21/2021

The “myth of the single choice,” that one decision can make or break everything, is to blame for people’s fear of taking risks, writes StubHub president Cassidy in her encouraging debut. The pressure to “make the right choice on a straight shot to glory,” she suggests, leaves people stuck in jobs that don’t suit them or on harmful paths, and the way out is to change one’s mindset and become more comfortable with risk. Cassidy’s program for doing so involves taking small risks “early and often,” acknowledging that growth isn’t linear, and embracing setbacks as part of the process. She urges readers to stay open to possibilities and wait for multiple options to appear (rather than jumping at the first available opportunity), stay in “discovery mode,” commit to always learning, and harness FOMO, because it spurs one to action. Cassidy has taken a number of big leaps in her own career, which she covers at too great length sometimes, to the point where the advice can get lost in the autobiography. Still, readers looking to play it a bit less safe will find this a welcome call to do so. (Aug.)

Publishers Weekly

Sukhinder is one of Google and Silicon Valley’s most successful and well-respected leaders. In Choose Possibility, she brings her unique style of authenticity, optimism, and hustle to help anyone unlock their career potential. ” — Eric Schmidt, Former Chairman & CEO, Google “Whether you’re twenty-five or forty-five, Choose Possibility offers a simple, clear, and effective process to overcome fear and unlock professional growth and fulfillment. ” — Stephen Kaufer, Co-Founder, President & CEO, TripAdvisor “Choose Possibility helps us see risk in an entirely new way. Sukhinder Singh Cassidy will inspire you to take small steps that can lead to extraordinary outcomes. ” — Susan Wojcicki, CEO, YouTube “Sukhinder Singh Cassidy is an extraordinary entrepreneur and businesswoman, and the ideas she presents in this book have the potential to make a tremendous difference in anyone’s career or life. ” — Spencer Rascoff, Former CEO & Co-Founder, Zillow “The ‘myth of the single choice,’ that one decision can make or break everything, is to blame for people’s fear of taking risks, writes StubHub president Cassidy in her encouraging debut.…readers looking to play it a bit less safe will find this a welcome call to do so.” —Publishers Weekly      “An indispensable guide to decision-making and risk-taking for anyone who finds themselves afraid of making a wrong choice in their career, from one of the most highly regarded female tech executives in Silicon Valley.”—Next Big Idea Club   —

From the Publisher