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Choose Possibility: How to Master Risk and Thrive

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Learn how to take risks, thrive and build your dream career.‘Sukhinder is one of Silicon Valley’s most well-respected leaders. Her unique style of authenticity, optimism and hustle will help anyone unlock their career potential’ – Eric Schmidt, former chairman & CEO, GoogleEach one of us dreams of possibility – in our careers and in our personal lives. But our pursuit of possibility is hamstrung by ‘The Myth of the Single Choice’ that has led us to believe that one large choice stands between us and success, and that a single failure may topple us should we choose ‘wrongly’. We let fear trump we become paralyzed.Sukhinder Singh Cassidy is one of the most well-respected leaders in Silicon Valley, but her path to success has been far from linear. While she has started three companies including theBoardlist, and has served as president of StubHub, she’s also encountered failed choices, misfires, and all other types of pitfalls that she had to learn how to overcome and incorporate into her new path forward.Drawing on her own experience and those of other leaders, Sukhinder shows that when people thrive, it’s because their fear of missing out on an opportunity overtakes their fear of failure, and compels them to take action. Better yet, they keep acting, building a fundamental risk-taking muscle that under weighs the importance of any single choice in favour of continually ‘choosing’. Choose Possibility is a thrilling and insightful new way to approach risk-taking and achieve lasting success.‘An excellent guide to help anyone learn how to take risks in their own careers and thrive’ – Kai-Fu Lee, chairman & CEO, Sinovation Ventures and author of bestseller AI Superpowers

273 pages, Kindle Edition

Published September 2, 2021

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Sukhinder Singh Cassidy

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5 stars
9 (21%)
4 stars
13 (30%)
3 stars
15 (35%)
2 stars
3 (7%)
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2 (4%)
Displaying 1 - 3 of 3 reviews
Profile Image for Victoria.
51 reviews1 follower
August 14, 2023
Was it the best book ever? No
Was it what I expected? Also no
Was it actually a decent book, with info that was well thought out and presented, despite not really being relevant to me? Yes

This is very specific to business decisions, especially upper management, and not a book based on every day decision making. This book is far more business category than self help, in my personal opinion, but I did still enjoy it in a “food for thought” kind of way. 3.5-4*
Profile Image for Kristina.
30 reviews
May 9, 2026
This book was okay but probably not very suitable for people who have already progressed in their careers and experienced quite a bit. I would recommend it to younger people who might just be fresh out of university or in their first job, and are maybe either doubting what they should pursue or how they should manage their career progressions and opportunities in life. For me (35 year old who has already finished undergrad + postgrad degrees and had various job roles) it wasn’t super valuable - I only learned new things or got inspired a couple of times.
Profile Image for David Fredh.
226 reviews3 followers
July 4, 2023
Take risks often and act on possibilities that opens up
Displaying 1 - 3 of 3 reviews