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Sukhinder Singh Cassidy

Seek Change, Take Risk, and Thrive (Even When You Fail)

4.5 (117 ratings)
28 mins

Brief summary

Choose Possibility by Sukhinder Singh Cassidy is a guide for women looking to navigate and succeed in male-dominated industries. It provides actionable advice and personal stories from successful women to empower readers to overcome imposter syndrome and embrace their potential.

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    Choose Possibility
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    Free yourself from the hero's journey and pursue multiple options at once.

    In the spring of 1993, Singh Cassidy was getting ready to launch her career. She was in her last semester of college and was eager to start the career she thought she wanted. Her goal was to become an investment banker, or perhaps a management consultant.

    She applied to big firms and dreamed of success: fat paychecks, power suits, and CEOs to her left and right. But spring and summer passed, fall came, and to Singh Cassidy’s increasing despair, not a single job offer materialized.

    Stuck at her parent’s home in Ontario, Canada, she watched as her former classmates set off to pursue their careers. She’d only just graduated but feared she’d already failed.

    The key message here is: Free yourself from the hero’s journey and pursue multiple options at once.

    Our culture thrives on heroic myths, stories where one person risks everything to vanquish a foe, prove her worthiness, and achieve her dreams. When we recall these stories, we often distill the hero’s journey into an unalterable path, forgetting that along the way, our hero faced many possibilities.

    The same can be said for our careers. When you imagine that a single choice defines you, you lose sight of the numerous other options out there. You catastrophize your setbacks and let your fear of failure gain the upper hand. You may even quit.

    But if, instead, you take on multiple, small risks, you’ll find you can build momentum and generate unforeseen opportunities.

    Take the example of Ashvin Kumar, who founded an e-commerce start-up in 2008. Instead of pursuing a single platform, his company launched almost 20 apps within 18 months. Each app took little in terms of capital, yet having so many meant lots of room for feedback. It was a numbers game. By expanding his options, Kumar reduced his risk and maximized his opportunity. Eventually, a live auction app, called Tophatter, took off and found millions of users.

    Back in 1993, a similar approach broke Singh Cassidy out of her post-college doldrums. She took a low-level job at a regional bank while pursuing several low-stakes risks: she applied to med school, passed Canada’s foreign service exam, and took a crack at the Law School Admissions Test.

    Most importantly, she accepted a train ticket to New York City. In the next blink, we’ll see how putting herself in the proximity of Wall Street unlocked new possibilities.

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    What is Choose Possibility about?

    Choose Possibility (2021) provides a roadmap to building the smarts and courage it takes to become a master of risk. Drawn from tech leader Sukhinder Singh Cassidy’s winding path through business, it debunks the myth that risk is all about singular, life-altering choices. Instead, it shows how risk-taking is a process, a practice and a skill that can unlock your professional potential.

    Choose Possibility Review

    Choose Possibility (2022) by Sukhinder Singh Cassidy is a book that explores the power of embracing new opportunities and making choices that lead to personal and professional growth. Here's why this book is worth reading:

    • With insightful anecdotes and relatable stories, the book offers practical advice on navigating life's uncertainties
    • It provides a framework for decision-making that encourages readers to step out of their comfort zones and embrace possibility
    • Through its thought-provoking insights, the book challenges conventional thinking and inspires readers to pursue their dreams and goals

    Who should read Choose Possibility?

    • Entrepreneurs, business leaders, and investors
    • People daunted by the unknowns of their work life 
    • Anyone who fears they’ve been too timid or reckless in taking professional risks

    About the Author

    Sukhinder Singh Cassidy is a leading tech CEO and entrepreneur with decades of experience in founding, building, and guiding companies such as Google, Stubhub, Amazon, and more. She’s the founder and current chair of theBoardlist, a marketplace that connects businesses to a growing and diverse pool of talent.

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    Jonathan A.

    Life changing. The concept of being able to grasp a book's main point in such a short time truly opens multiple opportunities to grow every area of your life at a faster rate.

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    Choose Possibility FAQs 

    What is the main message of Choose Possibility?

    The main message of Choose Possibility is to embrace uncertainty and create a future filled with endless opportunities.

    How long does it take to read Choose Possibility?

    The reading time for Choose Possibility varies depending on the reader's speed. However, the Blinkist summary can be read in just 15 minutes.

    Is Choose Possibility a good book? Is it worth reading?

    Choose Possibility is a thought-provoking and inspiring read. It offers valuable insights and practical guidance to navigate through life's uncertainties.

    Who is the author of Choose Possibility?

    The author of Choose Possibility is Sukhinder Singh Cassidy.

    What to read after Choose Possibility?

    If you're wondering what to read next after Choose Possibility, here are some recommendations we suggest:
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    • The Courage Habit by Kate Swoboda
    • The Daily Dad by Ryan Holiday
    • Competing in the New World of Work by Keith Ferrazzi
    • The Art of Laziness by Library Mindset
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