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 has made many wrong choices in her career, but has 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 will 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 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.
About the Author
Sukhinder Singh Cassidy is a CEO, board leader, and tech entrepreneur with over 30 years of experience scaling global pioneers in fintech, e-commerce, and SaaS. As the current CEO of Xero, a global leader in SMB software, she leads a multi-billion dollar business serving 4.6m users in more than 180 countries, driving AI innovation, and the company’s expansion into the US, including its $2.5 billion acquisition of Melio. Her executive experience includes scaling Google’s international operations to a multi-billion business and leading StubHub through its $4 billion sale in 2020. A three-time founder, she has successfully built pioneering brands including Yodlee, Joyus and theBoardlist.
With 15+ years of governance experience, Cassidy has served on the boards of global category leaders such as Urban Outfitters, Ericsson, TripAdvisor, and Upstart. She is an authority on digital transformation and global expansion, and the author of the Wall Street Journal bestseller, Choose Possibility. Her work has been profiled by Fortune, Forbes, The New York Times, the Wall Street Journal, Bloomberg, The Information, and numerous leadership podcasts.
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