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

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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 d 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.


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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 d 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.

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

  1. 4 out of 5

    M.

    It was a good read.

  2. 4 out of 5

    Simon

    Not just talk the talk but walk the walk - a refreshing perspective of risk-taking that enables us to rediscover ourselves! Summary: The main goal of this book is to encourage readers to take risks in order to reach their potential. Sukhinder breaks this down by offering compelling examples of how to develop our risk-taking muscle, dispelling the fallacies of risk taking, and illuminating how she has applied her risk-taking formula throughout her entire career in fascinating details! What I appre Not just talk the talk but walk the walk - a refreshing perspective of risk-taking that enables us to rediscover ourselves! Summary: The main goal of this book is to encourage readers to take risks in order to reach their potential. Sukhinder breaks this down by offering compelling examples of how to develop our risk-taking muscle, dispelling the fallacies of risk taking, and illuminating how she has applied her risk-taking formula throughout her entire career in fascinating details! What I appreciate most about Sukhinder’s book: Humility While Sukhinder’s storied career is built on her tenacity and hard work, she also recognizes that her success was built on the incredible dot.com era boom in the 90s and being part of once in a generation companies such as Amazon and Google at their humblest beginnings. It is these external factors that her risk-assessment advice for readers is built on, which brings to my next point. Practicality “Okay she is successful but how can I follow in the same footsteps?” This question may be top of mind for most readers. The beauty of this book is its practicality and the advice Sukhinder presents on how to quantitatively evaluate our risk and also mix this quantitative analysis with our natural instincts (aka “our gut feeling”). In addition, there are plenty of frameworks sprinkled throughout the book to help us not only gauge risks but also how to navigate career transitions, how to choose who we surround ourselves with, and advice on how we should approach work. Relatability You will feel like you’re on a rollercoaster as Sukhinder narrates her career journey. She dispels the belief that everything hinges on a single decision and walks you through the ups and downs of her career in fascinating details! Throughout her book, Sukhinder emphasizes that success is non-linear and that is okay and it is because of this non-linear trajectory that allows us to unlock more value in our careers. Overall, this is an awesome read for those who are career-driven as it forces you to rethink whether you are doing enough risk-taking. As highlighted in Sukhinder’s book, the price of inaction can be more costly than taking a risk! After reading her book, you will feel inspired and be more confident the next time you are faced with tough career decisions.

  3. 5 out of 5

    Neelam Babul

    Choose possibility is such an informational and insightful book for everyone who feels fear is holding them back from moving ahead in their career and life. I was impressed that the book was written by a female tech executive who added a much needed female perspective on career growth. It is a pivotal book in understanding how to learn from failure and use challenges as stepping stones to success. Sukhinder Singh Cassidy informs and guides the reader on how to deal with pitfalls such as making t Choose possibility is such an informational and insightful book for everyone who feels fear is holding them back from moving ahead in their career and life. I was impressed that the book was written by a female tech executive who added a much needed female perspective on career growth. It is a pivotal book in understanding how to learn from failure and use challenges as stepping stones to success. Sukhinder Singh Cassidy informs and guides the reader on how to deal with pitfalls such as making the wrong choices or dealing with unexpected issues in an analytical and positive way. I believe this is a must read especially during these uncertain times when we are held back by the covid 19 pandemic and are learning to adopt a new way of living.

  4. 4 out of 5

    Jonathan Rosenberg

    Sukhinder's "Choose Possibility" is an absolutely terrific read and sheds clear light on how to apply an aggressive and proactively informed approach to making decisions and taking risks as one navigates his/her career. Readers will enjoy the concrete examples that Sukhinder provides as she navigated the maelstrom of challenges building a tech career in Silicon Valley. The messages will resonate with anyone who gets stuck or is held back by fear of making a decision. So many people I have worked Sukhinder's "Choose Possibility" is an absolutely terrific read and sheds clear light on how to apply an aggressive and proactively informed approach to making decisions and taking risks as one navigates his/her career. Readers will enjoy the concrete examples that Sukhinder provides as she navigated the maelstrom of challenges building a tech career in Silicon Valley. The messages will resonate with anyone who gets stuck or is held back by fear of making a decision. So many people I have worked with and coached get mired down when they focus on circumnavigating failure and it leads them to take fewer chances. This book will show you that you make your own luck and serendipity requires choosing possibilities and constantly moving forward. At Google we often preach that teams should fail fast and then do post mortems. Sukhinder puts that advice into digestible examples that will help you succeed in the long run and convert inaction into a "Grow or Go" mentality. Success is about inching your way and leaping your way towards your goals. No perfect plan will get you there but rather cyclical efforts that constantly renew as the world, life and opportunities change. Most importantly, Sukhinder walks the talk not only in sharing the path from her own career but in illuminating a path for others. The most powerful people are those who help power flow to others and Sukhinder's work demonstrates that principle. More power to Sukhinder and thanks to Sukhinder and this book, more power to you!

  5. 4 out of 5

    Meagan

    I really, really appreciated this read on a lot of levels! Singh Cassidy's experiences are so wide-ranging--anyone can find something to relate to in her story. I particularly enjoyed the section (both in the introduction and in Chapter 1) on the Myth of the Single Choice--which "puts massive pressure on us to make the right choice on a straight shot to glory" (eARC loc 124)--and pivoting to choosing possibility. The latter reminds readers that "risk-taking is available to everyone, and so are it I really, really appreciated this read on a lot of levels! Singh Cassidy's experiences are so wide-ranging--anyone can find something to relate to in her story. I particularly enjoyed the section (both in the introduction and in Chapter 1) on the Myth of the Single Choice--which "puts massive pressure on us to make the right choice on a straight shot to glory" (eARC loc 124)--and pivoting to choosing possibility. The latter reminds readers that "risk-taking is available to everyone, and so are its rewards" (eARC loc 139). I've spent a lot of time over the years truly paralyzing myself with the single large choice, and was greatly encouraged by Singh Cassidy's encouragement to "seek to start and stay in thoughtful motion, knowing that every choice we make helps unlock the next possibility" (eARC loc 149). One lone choice, good or bad, doesn't have to preclude us from making another choice, and another choice. The incorporation of the hero's journey was particularly meaningful, challenging me to look not just at the big, single, macro-level decision a hero makes (Frodo volunteering to take the Ring to Mordor, anyone?), but the series of smaller, micro-level decisions he also makes along the way (Mines of Moria or the Gap of Rohan?) ... inferences all my own, of course. :) A fantastic read throughout, that started off strong and rode the wave all the way to the end. I received an eARC of the book from the publisher via NetGalley. All opinions are my own.

  6. 5 out of 5

    Trish Gilbert

    Have you ever been stuck at a crossroads unable to decide which path to take? Or so worried about making the "wrong" choice, you stayed with the status quo and didn't make a choice at all? Or had a career decision or job not go as planned and had feelings of regret looping over and over in your head? Or wanted proof that no one single choice or imperfect plan would define you? If you answered "yes" to any of those questions, or if not, and you're just interested in a great book on the topic of r Have you ever been stuck at a crossroads unable to decide which path to take? Or so worried about making the "wrong" choice, you stayed with the status quo and didn't make a choice at all? Or had a career decision or job not go as planned and had feelings of regret looping over and over in your head? Or wanted proof that no one single choice or imperfect plan would define you? If you answered "yes" to any of those questions, or if not, and you're just interested in a great book on the topic of risk, Choose Possibility is a must-read. The advice and opportunities for self-reflection in Choose Possibility are relevant and actionable regardless of your industry, geography, or where you are in your career. And the style with which Sukhinder Singh Cassidy writes is approachable and interesting - one of the few career-related books I didn't want to put down until I got to the end.

  7. 4 out of 5

    Kate Gronso

    This book was exactly what I needed to read to start to unlock what's next for me in my career journey. The combination of Sukhinder's vulnerability, frameworks, and tangible examples make this read actionable and inspiring, and have given me the confidence to face my fears in search of my own possibility. Having had opportunities to work closely with Sukhinder in the past, I am ever more inspired by the amazing career she has paved for herself and wholly appreciative of the opportunities to hav This book was exactly what I needed to read to start to unlock what's next for me in my career journey. The combination of Sukhinder's vulnerability, frameworks, and tangible examples make this read actionable and inspiring, and have given me the confidence to face my fears in search of my own possibility. Having had opportunities to work closely with Sukhinder in the past, I am ever more inspired by the amazing career she has paved for herself and wholly appreciative of the opportunities to have learned from her first-hand. I grew more than I could have imagined under Sukhinder's leadership, and look forward to the next steps in my journey with even more to think about and test from this book. Congrats on accomplishing another lifelong dream, Sukhinder!

  8. 5 out of 5

    Jolanta Szczerba

    ... and the wait is over! I could not put it down! Such a fabulous combination across reflecting on how we define risk-taking in our professional journey (debunking the myth of the single choice, for example, and rather remaining continuously open-minded to taking leaps along the way), vulnerability & authentic sharing of her own experiences in her incredibly successful business and tech career, and most of all, a real, hands-on tactical advice on how to think about (and act upon) risk/opportuni ... and the wait is over! I could not put it down! Such a fabulous combination across reflecting on how we define risk-taking in our professional journey (debunking the myth of the single choice, for example, and rather remaining continuously open-minded to taking leaps along the way), vulnerability & authentic sharing of her own experiences in her incredibly successful business and tech career, and most of all, a real, hands-on tactical advice on how to think about (and act upon) risk/opportunities, being in the mode of continuous discovery, learning, and embracing ups and downs of the journey as a path to personal and professional growth. Love it! Highly recommended!

  9. 4 out of 5

    Jagdeep Sawhney

    "Choose Possibility by Sukhinder Singh Cassidy” is a must-read as most of us have focused on avoiding failure for one reason or another and by doing so we take as few chances as possible. Sukhinder has provided practical framework paired with real-world examples that guides us to accept that failure is always a genuine option but it's the FOMO (Fear of Missing Out) that should instill the confidence in us to take chances “Risk-taking is not only for the thrill-seekers of this world. It’s for all "Choose Possibility by Sukhinder Singh Cassidy” is a must-read as most of us have focused on avoiding failure for one reason or another and by doing so we take as few chances as possible. Sukhinder has provided practical framework paired with real-world examples that guides us to accept that failure is always a genuine option but it's the FOMO (Fear of Missing Out) that should instill the confidence in us to take chances “Risk-taking is not only for the thrill-seekers of this world. It’s for all of us.” - Choose Possibility will change your way of seeing risk and inspire us to ACT to achieve our full potential in professional journey.

  10. 4 out of 5

    Cassandra

    I found the authors story captivating, insightful and inspiring. At my stage in life there feels like a persistent pressure to know exactly what my next steps will be and to feel assured in the direction I'm pursuing- accepting life's risks and failures feels liberating and exhilarating. I found the authors story captivating, insightful and inspiring. At my stage in life there feels like a persistent pressure to know exactly what my next steps will be and to feel assured in the direction I'm pursuing- accepting life's risks and failures feels liberating and exhilarating.

  11. 4 out of 5

    Carl059

    You make it easy to understand. Impressive Book Liqsquid Business You make it easy to understand. Impressive Book Liqsquid Business

  12. 4 out of 5

    Mira

    This was a great and insightful book. I gained a lot of perspective from reading this. I would recommend it.

  13. 5 out of 5

    Susan Walker

    This businesswoman gives the reader tips on making the right business decisions. The book is easy to understand and very helpful.

  14. 4 out of 5

    Amanda Perschau

  15. 4 out of 5

    Nimisha Pandit

  16. 5 out of 5

    Jackie

  17. 5 out of 5

    Ryan

  18. 4 out of 5

    Dennis

  19. 4 out of 5

    Matt Harward

  20. 5 out of 5

    Mohammed Hamed

  21. 4 out of 5

    Mariner Books

  22. 5 out of 5

    David Dickins

  23. 5 out of 5

    Hanna Rohana

  24. 5 out of 5

    Turki

  25. 5 out of 5

    Jeff McRitchie

  26. 5 out of 5

    Christina Chateauvert

  27. 5 out of 5

    Tanya Natividad

  28. 5 out of 5

    Miles

  29. 5 out of 5

    Nevaeha Ragins

  30. 4 out of 5

    Ree

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