How to overcome fear & build risk tolerance needed for growth [Bonus Episode]

With Sukhinder Singh Cassidy
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Show Notes

SHOW NOTES – EPISODE 202 [Bonus Episode]

TITLE: How to overcome fear and build risk tolerance needed for growth, Episode 202 [Bonus Episode]


TOPIC: Risk taking is important for securing new opportunities, growing our confidence, learning new skills, and for overcoming fear, but how can we grow risk tolerance and overcome fear when it’s FEAR that often prevents us from taking that risk in the first place? 

To answer that question, I’m drawing on an episode recorded back in 2021 that I’ve repackaged for you while I’m on break for the next few weeks. It contains some of the most helpful advice on the topic of building risk tolerance from someone whose successful career as a tech entrepreneur has been a product of the same thoughtful approach she shares in this episode. I think you’ll love it! 


Sukhinder Singh Cassidy and I sat down and recorded this conversation to promote the release of her book “Choose Possibility: Take Risks and Thrive (even when you fail).” She has been at the forefront of innovation in Silicon Valley for the past two decades— launching startups, leading the team that developed Google Maps, and overseeing numerous business transformations —  including most recently as CEO of STUB HUB. She not only practices what she preaches, but is sharing her thoughtful approach in ways that can help each of us build greater capacity for tackling risks, and the fear that can come with risk taking. 


  • Sukhinder shares her career journey and some of her earliest experiences with risk taking. 
  • Sukhinder and I talk about the importance of developing regular risk taking habits. Even small risks taken regularly help build momentum and confidence needed to tackle larger risks. 
  • Sukhinder shares what she calls “the universal risk taking equation” which includes understanding the difference between “fear of failure” and “fear of missing out” and how to leverage each.
  • We talk about why visualization is important and why it must include detailed strategies not just for visualizing success, but also (maybe even more importantly) for what you will do when you fall short of your goal or fail. 
  • We also talk about the connection between risk taking and confidence. 



While Sukhinder and I don’t specifically talk about the connection between influence and risk taking in this conversation, as I reflected on it, I love that there is a clear connection between this notion of activity seeking opportunities to learn, including from those experiences that didn’t turn out as we had originally hoped. Failures — or missing our mark — always provide some of the best learning opportunities, so long as our mindset is focused not on what we lost, but what we gained in the process and how we can use that knowledge going forward. 



BOOK:  “Choose Possibility: Take Risks and Thrive (even when you fail)” by Sukhinder Singh Cassidy

Full conversation with Sukhinder in Episode 159: it also includes her perspective on her work to get more women on corporate boards and why she founded The Board List

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