Taking Risks In Your Career: A Fireside Chat with Sukhinder Singh Cassidy

In partnership with the Morrissette Institute for Entrepreneurship, Sukhinder Singh Cassidy, HBA '92, shares insights on taking risks in your career from her book "Choose Possibility: Take Risks and Thrive (Even When You Fail)" during this virtual fireside chat hosted by Professor Eric Morse.

Risk Jenga Blocks

In This Session

For most people, there is lot of anxiety tied to taking risks: What if you make a big move only for it not to pan out? What if you end up regretting it? People often end up getting paralyzed by fear when it comes to taking risks in their careers, instead opting to play it safe. However, Sukhinder Singh Cassidy, HBA ’92, a leading digital CEO and entrepreneur, would argue that taking bold risks might be the best thing for your career trajectory.

In collaboration with the Morrissette Institute for Entrepreneurship, Sukhinder Singh Cassidy will join us to share her personal experience on taking risks in her career and deliver insights from her book Choose Possibility: Take Risks and Thrive (Even When You Fail) in a virtual fireside chat. During this event, Sukhinder and Eric Morse, Professor of Entrepreneurship, Executive Director of the Morrissette Institute, will discuss the secrets behind successful risk-taking, unexpected forces involved in shaping one’s career path, and the surprising ways risk-taking can shape your leadership journey.


Eric Morse

Eric Morse



Sukhinder Singh Cassidy

Author of Choose Possibility: Take Risks and Thrive (Even If You Fail)

Sukhinder Singh Cassidy

SUKHINDER SINGH CASSIDY is a leading digital CEO and entrepreneur with more than 25 years of leadership experience founding, scaling, and advising companies including Google, Amazon, StubHub, Yodlee, and more. She is currently Founder and Chairman of theBoardlist, a premium talent marketplace for diverse leaders to be recommended and discovered for board and executive opportunities.

Most recently, Sukhinder served as the leader of StubHub, the premier global consumer ticketing marketplace for live entertainment, which she and her team sold for $4 billion in February 2020. Earlier in her career, Sukhinder built Google’s business throughout Asia Pacific and Latin America, and served as the business co-founder of fintech pioneer Yodlee. Sukhinder also currently serves as a board director at Urban Outfitters and Upstart, and as a member of the global advisory board of TIME’S UP. She previously served as a board member at Ericsson, TripAdvisor, Stitch Fix, J.Crew and as a strategic advisor to Twitter. She is also a proven tech investor whose current and previous investments include Reformation, theRealReal, Sunbasket, Senreve and more.

Sukhinder has an undergraduate degree from the Ivey School of Business Administration at the University of Western Ontario, Canada and lives with her husband and three children in northern California.