CHOOSE POSSIBILITY: TAKE RISKS AND THRIVE (EVEN WHEN YOU FAIL)

Reviewed by Lynn Whitcher, Co-Director of Education for WWLF

On January 19, 2022, Julie DeCuypere and I had the pleasure of leading a book club discussion on Sukhinder Sing Cassidy’s book, Choose Possibility: Take Risks and Thrive (Even When You Fail).

Sukhinder Singh Cassidy is a technology investor, executive and entrepreneur. She has worked with various tech and media companies, including Google, Amazon and News Corp, most recently serving as President of StubHub, guiding it through the challenges of the COVID-19 pandemic as sporting events, concerts and other live entertainment were shut down, seemingly overnight, across the country. She is the founder of theBoardlist, a non-profit dedicated to improving corporate governance by increasing gender diversity on boards and Joyus, a video shopping platform for women.

Singh Cassidy attributes her impressive career to her ability to take risks. She also acknowledges that taking risks is hard. To put risk into the proper perspective, we must see the possibility that lies beyond any success or failure along our risk-taking journey. Taking risks is necessary, not just to survive, but to thrive.

For many of us, we assume – wrongly – that risk taking consists of a single leap that drives us either to success and glory, or to ruin. This puts massive pressure on us to get it right! The author calls this the “Myth of the Single Choice.” In reality, risk taking is less binary. The Jeff Bezoses of the world iterate their way to cumulative success through failures and achievement, stringing together a long series of choices, big and small, well advised or not. Although risk taking can result in bruised egos or loss of reputation, the upside is it can also lead to learning and insight, discovery of new opportunities, or even downright success!

For many of us, we will take the leap into action and choose risk when our fear of missing out outweighs the fear of failure. So how do we conquer our fears? Study and plan the upside, but also understand the impact and import of the downside as well. It is helpful to see failure as either a one-way door (where you cannot come back from your decision) or a two-way door (where you can return and recover). Most decisions are in fact two-way doors, with a path forward and a path back. Very few choices permit no way of recovery so plan for contingencies.

To become a great risk taker involves building risk taking muscle. Every day we delay taking risk, we put off our dreams. Every day we embrace taking risk, we are that much closer to achievement. Sing Cassidy challenges us to take risks today. This can be as simple as speaking up in a meeting or researching a new company or industry. Start now and look for opportunities to learn, grow, and discover every day. Once we get into execution mode, we will take risks in parallel putting multiple things in motion before we make larger choices. Think of it as applying to university, choosing safety schools and dream schools. Rarely do we lock ourselves into one outcome – we give ourselves options. It is no different when shaping our career.

Before taking the leap to a bigger risk, it may be helpful to place yourself in proximity to your dream. If you want to become an entrepreneur, join a startup and spend time learning from the founders. If want to transition to new sector, take meetings with people in the industry. Apprentice in the things you do not understand. Do not plan from afar.  

Surround yourself with the right people. Not only do you benefit from the support of leaders, professional coaches, or other personal champions, but great people tend to attract opportunity, receiving offers they cannot take. They often pass on these leads to folks in their networks who have performed well for them. This is why bosses, colleagues, and associates are our single best career network.

Whether you are working towards your next promotion, thinking about starting your own company, or looking for a career change, you have myriad opportunities to move yourself closer to your dream. Chose to move again and again and you will benefit from compounding benefits, taking hundreds, if not thousands of risks throughout the course of your career.

In the end, it is not what we achieve that makes us successful. It is our ability to keep taking risks, creating impact, and adapting as we go. Hopefully, as we rise, we bring along others with us on our way up.

To find about our next book read, or other WWLF events, check out our website.