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Jacket Notes: A masterclass in risk-taking

I wrote Choose Possibility after years of frustration with the myths people have about success, which have been worsened by places such as Silicon Valley. From the outside in, many presume that successful risk-taking is about making one large and scary choice; while this perception of risk may be inspiring in movies and books, it is rather daunting in real life. More importantly, it doesn’t conform with the reality of how success unfolds.

Outsize career success is the result of a series of risks taken, smaller and larger, with compounding benefits, including failed choices as much as winning ones. Success ultimately comes from committing to the process of choosing possibility continuously rather than treating risk as a one-off event. 

Ironically, the process of writing this book itself unfolded during one of the riskiest collective periods in modern history — the Covid-19 pandemic. I wrote the proposal for Choose Possibility in the winter of 2020, just as the company I was leading (StubHub) announced its sale to another global ticketing company.  I imagined I would be out of a job shortly after the transaction was concluded. While our $4bn acquisition was a successful professional win, it was also a large personal disappointment as I would not be leader of  the post-sale independent merged company.

But within 30 days of the sale, and while I was still holding the reins, the pandemic hit Europe and then North America. In the span of a week our company saw 20,000 global live events and entire sports leagues suspended. We lost virtually all our revenues and faced incredible and immediate risk to our business’s survival.

In the ensuing 60 days, we worked rapidly, company wide, to pivot every part of our business and restructure it so that we could sustain ourselves indefinitely. Only once the restructure was complete, did I finally leave.

So what does all this have to do with the book and the topic at hand?  As the leader of StubHub, I had spent a lot of my bandwidth before the pandemic trying to teach our company to be more agile. I witnessed first hand the fear people have of taking even small risks in a stable job and a mature company. But when true danger appeared, people were able to make new choices rapidly, taking risks far more quickly and intuitively to prevent further harm.  

For all of us, Covid-19 has become a masterclass in discovering our own agility. Knowing we have this capacity when times are bad, we also have this opportunity when times are better — to take little “upside” risks every day for more discovery, learning, ambition and impact. Learning to choose possibility continuously is also a great skill to have as the environments around us continue to change rapidly. 

I envisioned writing this book for many years. Writing it during a pandemic was unexpected, but a gift of its own kind. As people reach for new choices in a world of work that is itself fundamentally transforming, there has never been a better time for each of us to choose possibility and find new ways to thrive.

‘Choose Possibility’ by Sukhinder Singh Cassidy is published by Macmillan, R340