Risks and Rewards: How to Bet Big on Yourself


CEO and Internet entrepreneur Sukhinder Singh Cassidy poses in an undated photo, obtained by Reuters on August 23, 2021. Sukhinder Singh Cassidy / Anastasiia Sapon / Handout via REUTERS

NEW YORK, Aug. 24 (Reuters) – If you had to pick one word to describe the pandemic era, “risky” would be a strong candidate.

In a time of great risk to our health, careers and finances, Sukhinder Singh Cassidy has some advice. The former CEO of companies known as StubHub, Google and Amazon has written a new book “Choose the Possibility: Take Risks and Thrive (Even When You Fail)” on how to make risk work for you.

Cassidy told Reuters about betting big on yourself by breaking new ground and taking your career to the next level.

Q: In general, don’t people take enough risks in their professional life?

A: Humans are afraid of failure, of rejection, and afraid of looking stupid when trying new things at work. Many of these fears are ego-based: what will others think of us, or what will we think of ourselves if something goes wrong? The risks associated with ego hold people back in everyday working life.

Q: Is it time for people to take risks and forge new paths?

A: COVID has catalyzed many great learnings about risk as well as people’s desire to change their lives. In the rapid response to the pandemic, we have all learned something about our own agility and our ability to take risks and make choices quickly, ironically to avoid greater danger. It tells us that we are each capable of making new choices faster than we think, not only in times of crisis, but also when times are good.

Q: You say taking risks is like building muscle, what do you mean?

A: One of the myths I wanted to break is that some people are born to take risks. In fact, it is the opposite. Anyone can take risks in life – learn, discover, achieve their ambitions. You can find dozens of reasons to take risks and then take little ones every day. Then you have the benefit of learning from them if they work. And even if they don’t, you’ve vaccinated yourself against the fear of failure.

Q: Why can taking multiple risks be a smart strategy?

A: People generally want to move in series: make one choice first, then another. You don’t make consistent progress that way.

But if you pursue multiple risks, magical things start to happen. We diversify our risks because we are not betting on just one thing. And you benefit from the advantages of multiple possibilities:

A lot of people don’t know what they want, that way you can try on a lot of different things for the size.

Q: How risky is it not to take any risks?

A: Yes, because there is the opportunity cost of what you miss. It’s actually more of a career threat, if the rest of the world changes and you aren’t.

Research shows that the value of our skills degrades by 50% every five years. Think of it as if you weren’t moving forward in an escalator: if everyone is moving forward and you are still.

Q: Working moms in particular are overwhelmed right now, so what career advice would you have for them?

A: We often fear the risks of asking for what we need to make something work. This particularly applies to women. For example, when I was running international affairs at Google, a year after starting, I got pregnant. I wanted to keep the job, but we had to find creative solutions. So I asked them to pay a nanny and her travel expenses, which they did. I did not enter this titled discussion, but entered with a balance sheet.

Q: Silicon Valley has a reputation for being a “tech brother” culture, so what advice would you give women to be successful in this environment?

A: Go where your values ​​match. We all operate in environments of prejudice and prejudice, and it is more difficult for some people than for others. I have had success in companies with similar values, where I am free to be fully myself. If you feel safe, you will talk and ask for what you need.

Q: Is failure part of the process?

A: It’s about becoming a calculated risk taker, and that probably means more failures, but also more success. If you think about the choices you make over the course of your career, it should produce a solid success rate. Then you can reap the rewards of risk, regardless of the outcome of any individual decision.

Editing by Lauren Young and Richard Chang

Our Standards: Thomson Reuters Trust Principles.


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