Choose Possibility

Take Risks and Thrive (Even When You Fail)

by Sukhinder Singh Cassidy

4.4(101 ratings)

9 min read

Brief overview

This book challenges the idea that meaningful success stems from one gigantic leap. Instead, it shows how small, repeated risks propel you to learn faster, recover from setbacks, and feel more empowered. By reading it, you’ll see how to manage fear, keep momentum alive, and steadily convert potential risks into a rich string of achievements.

Introduction

We often think of success as one big, heroic leap. But this perspective can leave us frozen by fear of a single wrong step. This book flips that mindset and invites us to see risk-taking as an ongoing cycle of choices.

Much like training for a marathon, the idea here is to build endurance through steady, smaller actions. You learn from micro-failures, adjust your approach, and keep going—making the process less daunting and more rewarding over time.

By shifting our focus from “one shot” to “many choices,” we lower the stakes and expand our horizons. Whether we’re facing a career pivot or personal challenge, consistent movement beats waiting endlessly for the “perfect” plan.

"All life is an experiment. The more experiments you make the better."

Rethinking Risk

Risk is often portrayed as a high-stakes gamble, like jumping off a cliff with no guarantee of a safe landing. In reality, risk is a continuous process of experimentation—a way to test ideas and iterate, rather than all-or-nothing bravado.

We see examples everywhere: an optometrist deciding to close her mall shop to pursue a better fit, a manager stepping into an unfamiliar project, or a job seeker applying for roles that seem out of reach. In each case, risk is a collection of smaller steps.

When we broaden our view of risk to include multiple tries, we open ourselves to unexpected opportunities. Returning to safety is also easier when you’ve built a runway of incremental gains, rather than pinning your hopes on a single one-way door.

You don’t need any single choice to be perfect—you just need to keep choosing.

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What is Choose Possibility about?

The book "Choose Possibility: Take Risks and Thrive (Even When You Fail)" by Sukhinder Singh Cassidy fundamentally redefines how we perceive risk in pursuit of success. Through engaging anecdotes and insightful analysis, Singh Cassidy dispels the myth that success comes from one all-encompassing giant leap. Instead, she reveals that success is built upon a foundation of numerous smaller, manageable risks that incrementally build our capacity to thrive in uncertain conditions. The essence of the book lies in its approach to risk-taking as an ongoing practice, not just a one-time event.

Singh Cassidy shares invaluable strategies for harnessing fear and embracing adversity as an opportunity. She emphasizes the importance of aligning personal values with career goals, expanding one's network, and continuously seeking growth through iterative risk-taking. The book also introduces the reader to inspiring stories of those, including Singh Cassidy herself, who have turned failures into stepping stones for future successes. By offering practical examples and relatable narratives, "Choose Possibility" presents a realistic roadmap to turn missteps into progress and hesitancy into confidence.

This insightful exploration of risk is crucial not only for anyone looking to excel in their personal or professional life but for anyone seeking to cultivate resilience despite setbacks. Singh Cassidy's book serves as a compelling reminder that choosing possibilities, rather than fixating on potential failures, can lead to a more empowered and fulfilling life.

Review of Choose Possibility

"Choose Possibility: Take Risks and Thrive (Even When You Fail)" stands out for its approach to risk not as a glorified leap but as thoughtful, cumulative steps. Sukhinder Singh Cassidy lays out a clear, actionable strategy for viewing life’s uncertainties as opportunities rather than threats. The key strength lies in her candid storytelling, drawing from her own career journey and offering invaluable insights into how small calculated risks can lead to significant rewards.

What sets this book apart is its focus on practical application. Each lesson is enriched with real-life examples that illustrate how embracing small risks can unlock new achievements and career advancements, even after setbacks. Singh Cassidy’s engaging writing style ensures that concepts remain accessible, making it a suitable read for anyone, regardless of their familiarity with risk management or strategic planning.

The book is particularly relevant for readers at a crossroads in their lives, whether they are contemplating a career change or overcoming hurdles in their professional journey. Its professional yet conversational tone makes it a relatable guide rather than an academic lecture, ending with an encouraging note to continuously pursue new possibilities. In essence, "Choose Possibility" is a highly recommended read for its profound yet approachable take on the art of risk-taking.

Who should read Choose Possibility?

Aspiring Entrepreneurs: Learn how to create momentum through a series of small, strategic risks, rather than relying on one big move alone.
Young Professionals: Discover how to navigate the complexities of the job market and craft a career path that aligns with personal values.
Career Changers: Gain insights on reinventing careers through continuous iteration and risk-taking, no matter the industry.
Individuals Overcoming Career Setbacks: Find practical solutions for transforming failures into stepping stones for future success.
Managers and Leaders: Foster a risk-taking culture within teams while managing the balance between potential losses and future gains.

About the author

Sukhinder Singh Cassidy is a leading technology executive and entrepreneur with over 25 years of experience founding and scaling companies, including Google, Amazon, and StubHub. She holds a degree in Honors Business Administration and Management from Western University's Ivey Business School. Sukhinder has been recognized for her achievements, including being named one of the Most Creative People in Business by Fast Company and receiving the 2019 Ivey Alumni Achievement Award. Her book, "Choose Possibility: Take Risks and Thrive (Even When You Fail)", shares insights on risk-taking and career growth.