The “hero’s journey” is a standard approach for structuring stories of business success. Put simply, it involves a protagonist who sets off on adventure, encounters trials and a central crisis, and then returns a triumphant, changed person.

From business school case studies to business books and podcasts, this narrative conceit of an individual founder or executive facing a central crisis they must against the odds navigate is all around us.

“Ditch the hero’s journey,” is the title of the first chapter of Choose Possibility, a new book by Sukhinder Singh Cassidy. The longtime Silicon Valley executive—a veteran of Junglee, Google, Amazon, StubHub, and other startups—argues that thinking of risks as momentous, do-or-die trials is the wrong way to approach our lives and careers. Instead, she makes the case for continuously taking risks of all sizes, and judging their payoff over a longer timeline.

“Risk-taking is not the single, epic brush with peril that we imagine,” writes Singh Cassidy. “It’s the continuous process that we humbly but hopefully embrace, knowing that individual chances we take may be likely to fail but that our probability of overall success will increase as we iterate.” (p. xx)

Choose Possibility is an exhortation to take more career risks, a practical guide to how to smartly approach them, and a narrative of the ups and downs of Singh Cassidy’s own professional path.

Like other useful books about business and careers, it gets the reader thinking about their own process for navigating career moves. And it is peppered with glimpses into the dynamics of the Silicon Valley food chain, including Singh Cassidy’s own frustrations at various junctures where a role didn’t turn out to be what was promised, she lost a windfall gain from a company sale by investing it poorly, a startup failed to get sufficient market traction, or she was charged with selling off a business rather than operating it for growth.

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One of Singh Cassidy’s core contentions is that risk-taking is a muscle that strengthens as you exercise it. She aims to demystify it, by suggesting small ways for growing more comfortable, such as:

  • Reaching out to five new contacts who might be relevant to new career opportunities.
  • Speaking up at meetings, and asking the question on everyone’s minds but which no one else is asking.

Singh Cassidy argues that you don’t need perfect clarity to make career decisions, and that there’s often actually greater risk to staying in place. She recommends what she calls “pipelining in parallel,” exploring different possibilities simultaneously. Choosing Possibility also makes the case for prioritizing who you decide to work with and trying to spot macro tailwinds—such as the explosion of internet commerce that Singh Cassidy witnessed—that can accelerate your advancement.

At the heart of the book are structures for surfacing key elements to be able to embrace risk and make smarter decisions. These include:

  • Imagining what you might do to recover from a failure or reduce its impact. This can clarify that the risk is ultimately smaller than it might seem.
  • Separating out all of the risks and fears associated with a decision—which generally can be categorized as financial, reputational/ego, and personal. That helps in mitigating any tradeoffs.
  • Reducing the risk of failure by focusing on the potential downsides and confronting them before making the jump.

Singh Cassidy proposes a mathematical formula for assessing career decisions. On the positive side are the extent to which they:

  • Align with your goals
  • Fit with your passions, values, and personal strengths
  • Benefit from headwinds
  • Involve people you want to work with

On the negative side are the financial, reputational/ego, and personal risks. “Nothing clarifies our situations as much as the act of comparison,” Singh Cassidy writes. (p. 122)

She uses her own career as an example of the circuitous, cyclical nature of professional growth. Singh Cassidy struggled out of college to get a job, then had success at Merrill Lynch and the UK’s Sky broadcasting, then had an unsuccessful stint at OpenTV before a great experience at Junglee, which was sold to Amazon, and then Yodlee. She had a successful run at Google in several leadership roles, then by her own account experienced failure at Polyvore and Joyus, before becoming StubHub’s CEO and successfully selling the eBay unit just prior to the pandemic and launching theBoardlist on the side. “Risk is not what you think it is,” Singh Cassidy concludes. (p. xvii)

To be sure:

  • There are other critiques of the hero’s journey that Singh Cassidy doesn’t focus on: it overemphasizes the role of a single protagonist, when most business success is attributable to a team, and it occurs in the context of privilege that makes it easier for men or dominant societal groups to risk such a journey and triumph.
  • It’s important to question how much you can extrapolate from the experience of Singh Cassidy and her professional circle, given how much they have benefited from the unique over-abundance of resources, opportunity, connections, and favorable tailwinds in Silicon Valley over the past two decades. The risks and possibilities for the white-collar elite of the Bay Area are different from those of most American workers.
  • Relatedly, Singh Cassidy devotes limited focus to the inequality of opportunity and the polarized US economy that mean that many workers don’t have the possibilities she’s urging them to pursue, or need to assess risk in a very different context of not having an adequate safety net. Companies, including her former employer Amazon, have too often treated workers as human cogs in an internet-powered machine and deprived them of career flexibility and opportunity.

Choice quotes:

  • “All life is an experiment. The more experiments you make the better.” —Ralph Waldo Emerson (p. xix)
  • “If you want to learn the basis of risk-taking, there’s nothing better than learning how to sell.” (p. 15)
  • “Our educational credentials and experience might gain us entry into a profession, but they usually don’t differentiate us. What does are one or two qualities we possess in great abundance, ‘superpowers’ that make us especially effective in our pursuits.” (p. 106)
  • “Imagine your own role and draw a circle around it. This is what you own directly. Now let’s imagine each of us lining up our circles next to one another’s, and you’ll see that there are gaps between the circles. True owners don’t just own what’s in the circle. They also own everything that falls in the gaps.” —tech executive Sin-Mei Tsai (p. 163)
  • “Failing to choose leaves us far more vulnerable than any incorrect choice we might make.” (p. 207)

The bottom line is that Choose Possibility is an expert guide to cultivating and navigating career opportunities, while more accurately assessing and managing the risk they involve. It’s a worthy read for a knowledge worker interested in advice from a prominent Silicon Valley executive and her firsthand account of success and failure—though it doesn’t fully engage with the inequality of opportunity for too many Americans.

You can order Choose Possibility at or Amazon. (We may make a commission when you buy a book.) All page numbers referenced above are for the hardcover edition.

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