How Risk-Taking Leads to Lasting Success

April 15, 2022

Book Review by Taylor Berrett

Small Steps, Extraordinary Outcomes

We’ve all read the interviews of powerful, successful people. They breathlessly tell the story of the ‘big decision’ or ‘massive innovation’ they came up with, how they sweated it out in their garage or dorm room, then delivered their game-changer to roaring success.

But is that really the most common path to our entrepreneurial dreams? Or is the truth something less bombastic and yet far more obtainable? 

Enter Sukhinder Singh Cassidy and her outstanding book on leadership, entrepreneurship, and risk-taking, Choose Possibility: Take Risks and Thrive (Even When You Fail).

About the Author

Singh Cassidy certainly has the bona fides to back up her vision outlined in the book. Her most recent and prominent position was as the president of event ticket sales company StubHub, which recently sold for a few billion dollars. She’s also served on the executive team of eBay, was the founder and chairman of theBoardlist, and has been featured in everything from Fortune and Forbes to the New York Times and the Wall Street Journal. Named one of the ‘Most Creative People in Business’ by Fast Company, she’s been a leading technology executive, investor, and entrepreneur for years.

But does she have unique insights to offer? After all, not all successful people are great instructors. Fortunately, Singh Cassidy lives up to her reputation and then some.

The “Correct” Decision

One of the most satisfying and endearing elements of the book is the author’s willingness to dive deeply into her worst choices, biggest misfires, and most difficult challenges over the course of her career. In doing so, she provides insight into what is essentially her book’s thesis— that long-lasting success comes not from making some singular big decision that’s either right or wrong. Rather, success comes from a series of small decisions that are all made strategically and aimed at future possibilities.

Kicking Down Myths of Entrepreneurship

Singh Cassidy is at her best in Choose Possibility when she’s unashamedly destroying myths of success and systematically dismantling widely held beliefs. One of these is the idea of ‘passion bias,’ which she describes as a tendency to be more forgiving and overly optimistic about areas, industries, or pursuits that we’re naturally passionate about. Singh Cassidy says that a more rational approach, though it may not sound as good in an interview, is a more secure path to lasting success.

The Bottom Line

So, who is Choose Possibility for? It’s for anyone who walks on eggshells through their own career because they’re afraid of making the wrong choice. Sukhinder Singh Cassidy quickly sets those fears at ease by assuring us all that we will make the wrong choice, over and over again, but that our careers will become what we want them to be thanks to the way we turn those down moments into success.


Taylor Berrett

Taylor Berrett is a Contributing Writer at Soundview. He is also a freelance writer, editor, and host of the podcast Alone in a Room.