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Choose Possibility: Take Risks and Thrive

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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 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.

272 pages, Hardcover

First published August 17, 2021

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Sukhinder Singh Cassidy

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Displaying 1 - 30 of 50 reviews
Profile Image for Caro.
641 reviews23.5k followers
September 25, 2021
A book about taking risks, choices, making carefully-considered decisions as well as learning from mistakes when results are not what we expected.

There is a lot of valuable information for professionals at any level, and the author does a great job of describing her career progress, setbacks, and lessons learned from each experience.

She also makes emphasis on how critical the relationships we build along the way are, and that to succeed, you not only have to push yourself forward, but must also help grow and empower people along the journey.

I’m glad I picked up this book and highly recommend it to any career-oriented person.

Received ARC via Netgalley
Profile Image for Matej yangwao.
169 reviews11 followers
June 2, 2022
Book starts good about spreading risks between small and big risks and avoid taking bug decisions. Thus taking iterative risks over time and compounding.

Bit self-growth sauce inside.
It's full of obvious risk taking facts and a bit of stoicism that I detected.
Some risk taking doesn't yield returns immediately and multiple over time till you notice return.

I guess fair book about risk taking and placing small bets. Whenever you found your momentum of wins and opening new possibilities, you are raising possibilities for others as well.

Short chapter tells you about evaluating past risk and choices you've made and how you can weigh in into future choices.


>However, if we want to experience growth and success, we must try new things and take on challenges.

>Risk-taking is all about being discrete, monumental, and taking downright crazy actions that can’t easily be reversed.

>There are a lot of uncertainties surrounding risk-taking, and any choice we make might not work out as we desire.

>Hence, the power in risk-taking lies in combining many small and big decisions over time to produce impacts that inform our future choices.

>instead of thinking about implementing a big decision that will lead to our breakthrough, we focus on consistently taking small or big risks that will help us pursue our goals. We begin to see that every choice we make is a key to unlocking the next possibility.

>It’s okay to fail when you take risks because it helps you learn valuable lessons that eventually lead to growth.

>Having choices in life is a privilege, and if we’re fortunate enough to have them, we should exercise them.

>Our biggest risk is inaction because when we do nothing, we miss an opportunity to learn and grow.

>The highest reward for a person’s toil is not what they get for it but what they become by it.

>Taking risks will help you build confidence and develop new skills.

>We should always give our best shot at every opportunity. The idea is to chase multiple goals on different fronts rather than calculating risks and meticulously hatching a scheme on one plan alone, pursuing multiple opportunities in parallel.

>Prioritize your relationships with others because they play a significant role in your growth and will be the connections you’ll need later in life.

>As you attempt to take career risks, always remember that the people around you influence your success, not what you decide to focus on.

>Don’t think that being passionate about your job will make you reach the peak of your career quickly. Rather, focus more on the individuals who will journey with you on the path.

>Don’t strive to predict or control everything, including the future, rather seek opportunities to learn and contribute.

>Research has shown that humans have a biological and emotional need to be in control of their destinies.

>We can shape our future through our choices and how we respond to opportunities that present themselves to us, but that’s as much as we can do. There are other external factors like the environment, and those factors don’t stay static.

>The secret to success is choosing the next possibility and learning from the current one.

>Most decisions we make may not yield results immediately, but they may resolve in our favor over time and with multiple moves.

>The differences between impactful and ineffective people are not their personality types or intelligence; it’s about their approaches to execution. People who seek to make an impact prefer to take smaller risks to make them more successful and continuously achieve the expected result.

>We must continually identify our previous failures to build capacity and make better choices.

>Put progress over perfection: perfection is a myth. Rather than seeking perfection, start executing your plans. You will get more data and information during execution

>Be a truth-teller or truth-seeker: you must master how to speak frankly about your thoughts and seek to know the truth by getting candid reviews and feedback.

>We must see the possibilities, take risks in different capacities, and build momentum with every win. It is important to note that some things will be out of our control. In such instances, we should focus on what we can control.

>Regardless of how prepared and analytical we are about a particular risk, it is still possible to encounter setbacks. In such instances, it is vital to mirror the positives and watch for the opportunity to emerge from that situation.

>If our fear of missing out on opportunities (FOMO) exceeds our fear of failure (FOF) in exploring new things, we’ll act. But if not, we won’t take any action.

>We must believe that things are possible for us all the time because we believe in a possibility for ourselves, we create possibilities for others.
This entire review has been hidden because of spoilers.
Profile Image for Hussain Abbas.
103 reviews5 followers
January 3, 2022
This is a surprisingly elaborate book on risk-taking. It starts off slow with some powerful but quick insights on how to manage taking risks regularly. At that point, it felt that there wouldn’t be much else to cover in the book and it felt that way with some repetition. But newer chapters introduced auxiliary topics about impact, dealing with errors in impact, and many other things.

Regardless, the book could definitely have been shorter if the repetitions didn’t exist. I suppose they were there for emphasis but I was already sold on the perspective right in the beginning (it was that powerful). I was very happy with this book and surprised there is so much to write about this topics.
Profile Image for Hetal Sonpal.
Author 2 books34 followers
May 15, 2022
The one word to describe Sukhinder's book is 'honest'. She has been extremely candid, very thorough and totally down to eart in describing how she navigated through the various decisions that you took throughout her successful career.

I came across the book at Prime Ventures office in Bengaluru, one of the three partners of which, Amit Somani, I know is an avid reader, so I was confidence of book being a great one.

This is a great book for budding and existing entrepreneurs, people who are struck in their corporate careers, going through mid life crisis or approaching it, MBA grads, working women trying to find balance in their career, basically anyone !
Profile Image for Lim Lyn.
63 reviews2 followers
October 14, 2022
I loved the book and wish I had this earlier in my career . I was always afraid of change as I feared failure but with the book I feel more empowered to choose possibilities and just explore . The book includes stories from the authors experience and also her acquaintances and it gives insight of a journey of highly successful people . And it is true that we only see the success but not the failures , the book helps to dispel that myth and shares that with every choice there is bound to be success and failure and taking risk the focus is not if we just get the outcome we want but the learning and growth as it adds on to our career capital that we will use later on in our career.

Highly recommend this book

Profile Image for Emily Green.
598 reviews23 followers
December 5, 2021
I would like to thank Mariner Books and GoodReads Giveaways for providing an ARC of Choose Possibility by Sukhinder Singh Cassidy in exchange for a fair and honest review.

In Choose Possibility, Sukhinder Singh Cassidy champions risk taking, encouraging readers to make it a habit with which they feel comfortable. The book is geared towards decision making in one’s career, but much of the advice can be applied more widely to life. It is not a technical manual nor is it formally written.

Cassidy’s book is positive and inspirational. It combines Cassidy’s personal anecdotes and anecdotes from the lives of both famous and typical people with advice, explanations, and step-by-step processes for taking risks. Each chapter contains visuals, such as flow charts, to help the audience better understand processes. Chapters end with bulleted summaries.

I really enjoyed the narrative aspects of the book, especially the story of the woman who decides to make a career change to become a writer. (Surprise!) The stories help to reinforce not just Cassidy’s ideas, but also the real multitude of ways that a person can have a successful career.

Where Choose Possibility shines brightest is in its argument to being open to taking risks. A passage that particularly hit me was about self-knowledge and risk-taking,
"Given that we can become passionate about skills we develop or contributions we find we can uniquely make, we don’t want to anchor our career trajectories too firmly to a single, fixed version of what our passion is or must be. Rather, staying cued in to what we feel passionate about at any given time allows us to take into account what gives us energy or joy as we can make work choices, but not be totally boxed in by it (104 in the ARC)."
I have seen so many people begin in college thinking that they want to do something, but either not being able to find a job in their field or finding that once they are in a position, it is nothing like they thought it would be, they ultimately found their place on a different track. These people had to be willing to try something different and open to enjoying it.

Where the book gets problematic is that it is definitely for people who are financially comfortable. Several of the suggestions require some amount of savings, and all require the energy to research and pursue different options. There are many blue collar positions that afford neither of these options, as one can only live paycheck or paycheck or even accruing debt paycheck to paycheck. Some jobs are so exhausting that having any kind of energy for anything but work and some sort of limited personal life is nearly impossible. For people in this position, Choosing Possibility offers neither comfort nor much hope.

In the tough pandemic job market, where many people are rethinking their careers, Choose Possibility could prove to be extremely helpful.
1 review
November 5, 2021
Hệ thống chữa cháy tự động An Phát quy định về khoảng cách giữa các đầu phun

"Tôi chưa lắp đặt hệ thống chữa cháy tự động không phải vì không biết tầm quan trọng của thiết bị phòng cháy chữa cháy mà tôi muốn mình sẽ có một ngồi nhà mới, đến khi đó tôi mới đầu tư cho riêng gia đình mình", chia sẻ từ một cô nàng nhân viên văn phòng 29 tuổi.



Thiết bị PCCC phân phối bởi công ty An Phát


1. Dự định lắp đặt hệ thống chữa cháy tự động của cô nàng 29 tuổi

Hãy nghĩ mà xem, một căn hộ mới hoàn thiện được trang bị sẵn hệ thống chữa cháy tự động bằng đầu sprinkler thế hệ mới sẽ thật tuyệt vời biết bao. Chính vì thế, đến năm 29 tuổi, khi có khả năng mua sắm một căn hộ chung cư mới với đầy đủ nội thất tôi mới quan tâm tìm hiểu đến thiết bị chuyên dụng này.


Năm nay tôi tròn 29 tuổi, nghĩ đến ở độ tuổi này mà chưa mua được một căn hộ của riêng mình thì có phải là hơi chậm trễ quá không. Nhưng bản thân tôi vẫn đang rất cố gắng để thực hiện ước mơ ấy,  tôi cho rằng không bao giờ là quá muộn; chỉ cần bạn có tinh thần muốn thay đổi, quan tâm đến chuyện mua nhà và lắp đặt đầu phun chữa cháy là được rồi.


Câu chuyện liên quan đến an toàn cháy nổ lúc nào cũng có vẻ vô cùng cấp bách. Tuy nhiên, tới khi sở hữu được nó, bạn sẽ hiểu lý do vì sao tôi sẵn sàng làm việc liên tục nhiều năm chỉ để chuẩn bị tiền trang bị hệ thống PCCC đặc biệt này.



Nhờ trước đó có tìm hiểu thông tin về thiết bị PCCC nên tôi cũng đã chọn được cho mình một đơn vị thi công như ý. Đó chính là đại lý An Phát.
Tôi đã dự định chọn mua căn hộ ở một dự án thuộc khu vực Quận 7 với mức giá cực kỳ phải chăng. Thế nên tôi có đủ kinh phí để trang bị thêm hệ thống chữa cháy cho nơi mình sinh sống.

2. Hàng xóm nói gì khi trong khu có nhà trang bị hệ thống chữa cháy

Hàng xóm sống tại khu vực mà tôi dự định sẽ mua nhà có nhiều người cũng đã gần 40 tuổi nhưng nhìn chung họ vẫn chưa thực sự quan tâm đến vấn đề PCCC là mấy. Chị hàng xóm đối diện dù có điều kiện kinh tế tốt, hoàn toàn có khả năng đầu tư một hệ thống chữa cháy cho riêng căn hộ của mình nhưng chị ấy không hề tìm hiểu gì về thiết bị này cả. Nhìn chị ấy, tôi thấy rất lo lắng, vì nếu chẳng may có chuyện gì xảy ra thì không biết chị ấy sẽ giải quyết ra sao.



Thiết bị PCCC phân phối bởi công ty An Phát


Việc trang bị những thiết bị chuyên dụng để đảm bảo an toàn vốn là việc mà ai cũng phải nghiêm túc đầu tư, từ thời gian cho đến tiền bạc. Có như vậy thì mới tìm được cho mình một nơi phân phối đầu chữa cháy sprinkler hiệu quả cho gia đình. Căn hộ nhờ vậy mới trở nên an toàn, phòng tránh được các rủi ro về hỏa hoạn được.


Từ nhỏ tôi đã được thầy cô giáo trên trường đào tạo và nhắc nhở về tầm quan trọng của phòng cháy chữa cháy, tôi còn được tham dự các buổi huấn luyện đào tạo sử dụng các thiết bị cứu hỏa. Thế nên đến đi làm thì tôi càng quan tâm đến việc này hơn nữa. Tôi tự mình tìm hiểu về hệ thống sprinkler nhiều hơn để có đầy đủ kiến thức chuyên môn khi chọn lựa nhà phân phối. Tôi đã quyết tâm rồi, khi mua được nhà mới, tôi sẽ lắp đặt ngay đầu phun chữa cháy An Phát cho nhà mình. 


3. Tiêu chuẩn lắp đặt hệ thống chữa cháy

Nếu tầm nhìn của tôi có thay đổi, quan điểm PCCC của tôi vẫn sẽ giữ nguyên như cũ. Bởi tôi nghĩ rằng, cần có phương pháp phòng chống cháy nổ trong căn hộ của mình để ngăn ngừa các nguy cơ hủy hoạn. Cuộc sống bây giờ đã có nhiều lựa chọn hơn, mỗi người sẽ thích một giải pháp riêng, nhưng tôi thì luôn tin vào hiệu quả của hệ thống chữa cháy Tyco mà An Phát phân phối và lắp đặt.



Thiết bị PCCC phân phối bởi công ty An Phát


Những quan niệm và ý kiến va chạm nhau, nhưng tôi cũng như rất nhiều người khác đều đồng ý rằng: "đầu chữa cháy sprinkler bằng nước là phù hợp nhất đối với dạng căn hộ chung cư và nhà ở". Góc nhìn của bạn có thể khác tôi, nhưng ý kiến mà tôi đưa ra lại chính là ý kiến chung của đa số các chuyên gia và kỹ sư trong ngành PCCC.



Thiết bị thực sự cần thiết đối với từng không gian sống khác nhau. Đặc biệt là những nơi đông dân cư, dễ xảy ra những tình huống nguy hiểm do cháy nổ.
Nếu muốn thu hút dân cư đến sống tại dự án mới thì việc lắp đặt hệ thống cứu hỏa tự động là việc làm mà chủ đầu tư nào cũng mong muốn.
Ngày xưa, khi PCCC còn chưa được phổ biến rộng rãi, đã có rất nhiều vụ hỏa hoạn đáng tiếc xảy ra, gây thiệt hại nhiều cả về người và của. Bây giờ, những vấn đề cháy nổ được đề cập nhiều hơn, người dân ngày càng nâng cao ý thức phòng ngừa, tìm hiểu về sprinkler các loại để chủ động lắp đặt, nhờ vậy, tỉ lệ hỏa hoạn xảy ra được giảm rõ rệt.
Việc dựa vào công ty tư vấn, phân phối các sản phẩm chữa cháy uy tín để lắp đặt cho gia đình cũng rất khôn ngoan. Họ sẽ cho bạn lời khuyên loại sprinkler nào là phù hợp để sử dụng.

Tìm hiểu về hệ thống chữa cháy để lắp đặt thì không khó, tuy nhiên bạn cần phải tự nâng cao nhận thức của mình về các sản phẩm sprinkler trên thị trường để chọn mua đúng hàng chính hãng chất lượng.

Profile Image for Simon.
1 review3 followers
April 25, 2021
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.

Profile Image for Mikala Charron.
733 reviews14 followers
January 19, 2022
What a slog at the end. The first 2 parts I fully appreciated, but I didn’t see the point of the 3rd part. Also, it just felt like a ton of name dropping at some points and showing proof companies made money. This book is going to help me think of my professional goals and I’m glad I read it, but 220 pages have never felt so long.
416 reviews5 followers
April 8, 2024
"Choose Possibility: Take Risks and Thrive" by Sukhinder Singh Cassidy offers a compelling narrative on the role of risk-taking in shaping one's career. Through the perspective of an accomplished business executive, the book challenges conventional wisdom about risks and lays out a strategic roadmap for leveraging them to one's advantage for career growth.

Cassidy challenges the traditional tendency of risk aversion and argues that risk-taking is inevitable. Given the unpredictability of the future, attempts to sidestep risk are futile. She posits that by proactively engaging with risks, we not only open up a myriad of possibilities but also build up resource reserves to withstand future failure. The book suggests that it's our emotional response to failures, rather than the tangible setbacks, that deters us. By cultivating a habit of embracing risks, we develop the “risk-taking muscle” and overcome the fear of failure. Cassidy advocates for taking incremental risks to steadily accumulate professional and personal growth, ensuring that setbacks are within our tolerance. Moreover, she introduces a refreshing perspective that 'failure' in the conventional sense can paradoxically lead to enhanced skills, reputation, and unforeseen opportunities. Through this lens, "Choose Possibility" illuminates the transformative power of risk-taking, portraying it as a catalyst for personal and professional evolution, rather than an obstacle to be feared.

Crucially, it's essential to bet on ourselves by selecting opportunities that resonate with our innate strengths. It's important to acknowledge that our true strengths may not always align with our passions, and identifying our unique "superpower" can sometimes be elusive. Thus, actively seeking feedback becomes vital in uncovering and harnessing this superpower to fulfill our ambitions.

In evaluating business opportunities, it's crucial to recognize that success is frequently more influenced by external conditions than by individual effort and skill. Favorable market conditions, or a "tailwind," can magnify and elevate our successes. Conversely, challenging conditions, or "headwinds," present valuable chances to assert our leadership qualities and resilience. Grasping the nuances of these business climates allows us to strategically direct our efforts and capitalize on opportunities for expansion.

Adopting a strategy of parallel betting can further enhance our chances of success. While dedicating ourselves to a primary venture, maintaining awareness of additional prospects is crucial—not just as potential next steps but also as safety nets should our current endeavor falter. The process of identifying, assessing, and engaging with these opportunities requires time. By navigating multiple opportunities simultaneously, we broaden our exposure to potential successes.

Moreover, the essence of risk-taking transcends the mere attainment of a particular objective; it's fundamentally about personal development. Failure in specific projects can still yield significant gains in experience, self-confidence, reputation, and relationships. This understanding not only informs our approach to taking risks but also allows us to view outcomes through a multifaceted lens, maximizing the benefits derived from our endeavors.

Apart from its insights on risk-taking, the book provides invaluable advice on career development, including strategies for networking, enhancing impact, and achieving work-life balance. This guidance is particularly beneficial for professionals in the early to mid-stages of their careers who are aiming for leadership roles.

"Choose Possibility" draws primarily from Sukhinder Singh Cassidy's own experiences and reflections, rather than empirical studies or research. The narrative is marked by honesty and introspection, eschewing any tone of self-praise or promotion. Notably, Cassidy offers a candid evaluation of how fortune, external influences, and her decisions have shaped her journey, providing readers with a nuanced understanding of success. The book is both enjoyable and thought-provoking. However, readers are advised to judiciously assess the applicability of Cassidy's insights to their personal career paths and ambitions, considering their unique goals and abilities. Despite this, her perspectives on embracing risk and making informed career decisions stand out as significant contributions to career development literature.

Overall, "Choose Possibility" is a valuable addition to the tapestry of discourse on career advancement. It offers invaluable insights into navigating the complexities of the professional world through strategic risk-taking. Its blend of personal narrative with actionable advice makes it a compelling read for those at various stages of their careers, especially those aspiring to leadership roles.

3 reviews2 followers
August 26, 2021
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!
Profile Image for Meagan | The Chapter House.
2,053 reviews49 followers
August 31, 2021
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.
Profile Image for Priyanka Singh.
13 reviews7 followers
March 6, 2022
The author does a terrific job of taking the readers through her journey of choosing possibility and pivoting through variety of roles only to become CEO of some of the great companies. Her story is inspiring and compels everyone to take calculated risk instead of being stagnate. She also emphasizes on the fact that failures are indispensable part of anyone's journey but if someone is ready to take the failures in positive stride and keep moving forward, the long term output will always be rewarding.

However, I would have loved if she could also have talked more about her personal life as it seems she has a great family as her anchor which she could always fall back on. One may argue that she does not need to as this is a complete guide on the professional choices but I disagree. Take a closer look at anyone's career who rose to the top and you will realize that personal life and professional life are mostly intertwined and they need to be in harmony. As Jeff Bezos said "It's not a balance. It actually is a circle".

Nevertheless, I still love this book which inspires everyone to choose possibility and take risks.
Profile Image for Nick.
217 reviews6 followers
June 28, 2022
Cassidy's insight: an interesting career isn't a linear path, made in a single, momentus decision. It is, from her experience, at best an ongoing experiment, a set of measured risks, with steps forwards and backwards throughout. So, here, she focuses on learning how to take those risks, by introducing a sensible method of facing fears (financial, ego), assessing strengths, goals, and values, and understanding the power of your social network and the forces of the market, which function as both tailwinds and headwinds at different times. This is a good and critical antidote book to the "define your goal, work towards it" approach of career advice, and is especially useful for multitalented people facing intense career pressure.

Having said that, this is also a book from one of the champions of Silicon Valley. Expect lots (and lots) of brand drops, big name drops, and very long twists and turns in Cassidy's own career, not all of which were "successful" but which, on retrospect, put her in a position to assess and take the next risk. I could have done with less of the drama and more of the framework, but it was interesting to see it in action in her own life.
Profile Image for Brit MacRae.
221 reviews21 followers
March 31, 2025
I heard Sukhinder speak at a conference a few months ago and was blown away by how candid and grounded she was. That talk (plus a dear friend who highly recommended it) pushed me to pick up Choose Possibility, and I’m so glad I did—she brings that same honesty to every page.

To start, this book isn’t just sugar-coated platitudes about success. It's a walk through the messy, unfiltered journey of risk-taking, full of wrong turns, hard lessons, and then eventual wins. This also isn’t a “just jump!” / toxic positivity manifesto. It’s more like: “Yes, jump—and here’s what it actually looks like to land, tumble, get up, and keep moving.”

She weaves in stories from her own career (Google, startups, CEO gigs) and others. The result? You get a clear look at the patterns behind thriving careers, not just the polished highlights.

The biggest lesson that hit home for me: success doesn’t come from avoiding failure, but from choosing again and again. Risk is a muscle. Failure isn’t the opposite of success—it’s baked into it. And every decision, whether it leads to a win or a faceplant, adds to your career capital.

The book left me feeling bold. Highly recommend!
Profile Image for Karen Hewitt.
318 reviews2 followers
April 6, 2023
Alright, folks, let's talk about Choose Possibility by Sukhinder Singh Cassidy! This book is like a shot of espresso for your soul ☕️.

Sukhinder's writing style is so refreshing - she's like the cool auntie who always knows the right thing to say. And her message of choosing possibility and embracing change is just what we all need right now.

I loved how she shared her personal stories and struggles to illustrate her points. It really made the book feel like a conversation with a wise friend who's been through it all.

But don't get it twisted - this book isn't all warm and fuzzy. Sukhinder challenges us to step out of our comfort zones and take action towards our dreams. And her practical tips and exercises are just the kick in the pants we need to make it happen.

If you're feeling stuck or just need a dose of inspiration, Choose Possibility is the book for you. Trust me, you won't regret it! 😎📚
Profile Image for Gabrielle.
274 reviews12 followers
October 28, 2023
I came to this book off the recommendation of one of my favorite podcasts. The episode was on taking risks, and it was focused more on personal life, so I was surprised to learn this book focuses on professional risk-taking. I love professional and career focused content, so I stuck with it. Overall, the book is valuable and did have some great takeaways for how simple yet calculated risks can level up ones life and career. In some parts, it felt like a memoir of the author's career choices, and then, in other parts, the vignettes felt like a brief history of success and failures in the tech industry. While much of the content was framed on tech, I would have loved to have the author talk a bit more about how the tips and recommendations could be applied to other careers and areas of life. This book is definitely of use, and I recommend it for a career toolkit.
51 reviews1 follower
December 20, 2021
Pleasantly surprised - mostly cos the title and tag line don't do it full justice. In addition to breaking down (or rather, reframing) what it means to take 'risks' in your career, the author does a great job highlighting through her own experience and other anecdotes, that successful careers aren't always linear. This was refreshing to read because the author has taken so many different routes in her career - far from the traditional path of staying in one job / company for long and moving upwards. In that regard,I think this is worth reading for anyone trying to figure out career decisions or simply, looking to take stock of how far they've come and redefine career success for themselves. Very well structured and insightful.
1 review3 followers
August 5, 2021
... 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!
1 review
August 19, 2021
"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.
Profile Image for Heng.
152 reviews
August 11, 2022
While there were some useful frameworks throughout the book, much of it is derived from conclusions of one person's life in which a couple of "risks" taken paid off in unpredicted ways. This read more like a memoir of the author's career with her conclusions of what worked for her in hindsight extrapolated as general advice. I read this at the same time as Backable, which I felt was much more packed with various anecdotes in support of the author's claims as well as being much more concisely and entertainingly written.
16 reviews2 followers
October 8, 2023
I found this book useful in that it gave me an insight into the CEO who runs a company I have invested in so important for me for that purpose.
Some key take outs from a career perspective:
- get options on the table for yourself by being a bit more courageous, building relationships and aligning with people you admire rather than a role or company you long to work in.
- look at environmental trends to support a career move so you are moving with the general flow of progress rather than getting stuck in an obsolete or dying industry.
Profile Image for Austen Sugiarto.
9 reviews1 follower
October 8, 2024
As the title suggests, this book dives into how we make life choices and perceive risks. The author reflects on her own career journey and that of other prominent figures, demonstrating the benefits of embracing possibilities and daring to take risks. Though some sections felt a bit long-winded, the insights offered are thought-provoking, encouraging readers to reevaluate their relationship with uncertainty. Overall, it's a valuable read for anyone looking to adopt a fresh perspective on decision-making and risk-taking.
21 reviews
September 25, 2025
Difficult for me to rate as I was impressed by her career journey and do feel as though there was some good inspiring wisdom/reminders to take risks, however it was presented with a ton of name dropping and the risk taking was in the context of what seemed to be a very privileged situation, which were a turnoff. Overall valuable perspective but I wish presented more as a memoir and a few pages shorter.
Profile Image for Gurleen.
192 reviews
December 16, 2021
This was not the average "this is my life and you should be in awe" story. I feel like I've truly walked away from this book having learned and that's a priceless experience. I believe Cassidy has a lot to share with others that we all can learn from. I definitely recommend this to anyone at any point in their career!
Profile Image for Shevon Quijano.
293 reviews
July 27, 2022
Loved the premise of setting expectations when it comes to risks and realizing that success is a combination of little steps/decisions. I also enjoyed the message to be open to opportunities, intentional with growth and patient with the overall path of life.

My one critique is that this book could've been edited wayyyy down though. More verbose than necessary.
Profile Image for Jessica Goodman.
536 reviews17 followers
February 16, 2024
I was attracted to this book because of the foreword by Kim Scott (love her books!) so was happy to get a copy on NetGalley. I enjoy business books and the author generously shared her career journey and her life lessons along the way, plus sharing stories from her friends - I find personal stories really bring these types of books to life.
12 reviews
August 26, 2021
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.
Profile Image for Johannes Klumpe.
29 reviews
March 26, 2024
I really liked the perspective on risk taking and non linear rewards in an industry where things are evolving very fast. This book was able to capture this and also presented a very intuitive model for what a career path in tech can look like.
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