Choose Possibility! The secret to risk taking is planning for failure – serial entrepreneur & author, Sukhinder Singh Cassidy (Episode 159)

With Sukhinder Singh Cassidy
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Show Notes

Taking risks— both large and small — is part of life. From the day-to-day choices we make, to the biggies like changing jobs, changing careers, taking a break, getting married, having children, and moving across the country— all involve some degree of risk. Do we take the safe and steady route, stick where we are, or do we roll the dice, throw caution to the wind and really go after what we want? Make no mistake, not deciding to take a risk IS deciding. 

If the thought of all of this risk-taking makes you a little uncomfortable, join the club — you’re human!

In Episode 159, we’re talking about how we can teach ourselves to separate and understand calculated risk-taking from fear and emotion. They are not the same things. Even more on-point, how do you build the confidence needed to put fear into context so that you can take smart, calculated risks, ones that help you leverage your experience, challenge you to grow, and that help you create greater value for yourself and others?

My guest in Episode 159 is Sukhinder Singh Cassidy, a serial entrepreneur who has been at the forefront of innovation in Silicon Valley for the past two decades. She’s launched startups, led the team that developed Google Maps, led numerous business transformations —  including most recently at STUB HUB, and she’s embraced risk over and over and over again. 

Today’s conversation is all about risk-taking. Sukhinder shares her approach which is very different from how most of us have been taught to think about risk — and the fear that can often accompany it. 

Sukhinder has written a terrific book, “Choose Possibility: Take Risks and Thrive (even when you fail). While the book won’t be available until August 17, 2021, you can pre-order now at the link above. Our conversation in Episode 159 gives you a sneak peek into some of the tremendous wisdom and perspective that Sukhinder shares in the book. 

Sukhinder also shares an additional bonus item with YOU: a risk tool she developed to help you figure out what type of risk taker you are. That insight can help you better identify the real obstacles standing in your way, and can give you perspective on how best to plow through them. 

One piece of advice that especially resonated with me was Sukhinder’s recommendation to plan for both the failure, as well as the success. She talks about why this approach has mattered so much in her own life and career. She also shares a trick for dealing with fear by separating FOF (fear of failure) from FOMO (fear of missing out). 

We trace Sukhinder’s story from how she grew up, to her early career at Merrill Lynch — where she worked in business development (or as she refers to it in this episode as “biz dev”) — to her work in Silicon Valley. 

We also talk about her founding and launch of The Board List and the challenges associated with getting more women and minorities on corporate boards. 

There is lots packed into this conversation! 

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