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Ditch The Hero’s Journey

Popular culture has never been more interested in heroes. From Hollywood’s reliance on superhero franchises, to the news media’s readiness to build up...

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This story originally appeared on ValueWalk

Popular culture has never been more interested in heroes. From Hollywood’s reliance on superhero franchises, to the news media’s readiness to build up (and then tear down) leaders, we’re fascinated by people who do the extraordinary. That makes for spectacular stories and attention-grabbing journalism. But it’s a disaster for our careers.

belkacemyabadene / Pixabay - Valuewalk

Q2 2021 hedge fund letters, conferences and more

The Hero's Journey

When it comes to our own life choices, we’ve too long subscribed to the “hero's journey.” This concept, developed by Joseph Campbell, started out as a fairly technical account of mythmaking. It centered on how societies reinforced order while allowing certain people to break free, surmount a tremendous obstacle, experience transcendence, and return back to move the society forward.

Popular films, from Star Wars to the Fast and the Furious, have secularized and propagated the journey as a fable of great risk and accomplishment. Anyone could be a hero—if they took a big and scary chance. Either succeed mightily, or face certain disaster based on this binary choice.

We love the romance and adventure of epic journeys, probably even more so after a year of pandemic-induced soul-searching.  But instead of teaching us how to thrive, this “succeed or fail greatly” version of the hero's journey leaves most of us fearful at the thought of taking a risk at all, professionally or personally.

I understand this fear well, having felt the pressure of a single large choice multiple times in my own career. I remember one particularly big decision—to leave a senior position at Google to become a first-time CEO at a startup.  I took the leap, but then fell out with the startup’s founder and was out of a job six months later. I was consumed with anxiety that this single costly failure would prove ruinous to my career. Only it didn’t.

“The Myth of a Single Choice,” as I call it, keeps many of us from embracing a new goal. But our fears are misplaced; it’s time to replace this mythical model in our heads with a more realistic and constructive perspective on risk-taking that can truly drive career success.

Careers As Portfolios

To do so, we can look at the financial services industry. Venture capitalists have learned not overweight any single choice, but rather to place multiple bets, some smaller and some bigger, and to focus on people and markets more than specific products. Asset managers likewise preach selective diversification in building a high-return portfolio. They’ve learned to take a series of risks and learn from successes and failures. They become calculated risk-takers over time, while building compounding positive returns overall. The same logic applies to our careers.

In my own career, I learned to treat risk-taking as a muscle, built up  through consistent, careful repetition, rather than a one-off event. In the last twenty years I’ve made a series of career decisions to join, execute, lead and leave companies, and enjoyed compounding professional benefits from these choices Some of those experiences were “successes,” others “failures,” yet the relationship between any single risk taken and reward achieved been much less clear. A success might boost my bank account more, but a failure often led directly to other successes, and vice versa. I’ve had small choices result in big outcomes, and big choices that resulted in only small wins. And almost none of my choices were binary.

Rather than a focusing on a single choice, the most rewarding careers are built progressively as a series of choices, impacts and then more choices.  They involve taking a variety of risks. Some work as expected, some don’t, but most push us forward and make us smarter in choosing our next possibilities. A single reward is rarely proportionate to the specific risk taken, and often the rewards aren’t apparent for a long time. But we stay in the game by continually choosing and getting better with each choice.

In the moment, a big choice may feel singularly daunting, and therefore paralyzing. You think, “I’m no hero, I’m not ready to risk everything; my life is ok as it is,” and so you hold back. But even the biggest opportunities can usually be broken down into a set of manageable risks and incremental choices that you can start on today.

This is all the more true now, when the “key choices” of earlier generations have lost most of their power. Instead of the usual path of prestigious consulting firm, MBA, and career ladder at a big company, people are finding opportunities in all sorts of entrepreneurial experiences, including side hustles. Disruption continues to ripple throughout the economy, technology-induced, pandemic-induced, or as a result of other new forces. These disruptions bring with them non-linear paths that may drop opportunity into your lap when you don’t expect it – as long as you’re in the game and ready to take the risk.

In an increasingly volatile macro-environment, what it takes to lead has also changed. In fact, researchers at LinkedIn found that the quickest path to the CEO seat is a winding one, through multiple functions. CEOs who reach their position faster than average rarely had the usual pedigree. They might take on a smaller job in order to gain skills or experience, accept a position for which they felt unprepared, or volunteered to tackle a tough business problem. It was making several moves flexibly, rather than making one single linear move, that made these careers successful.

For most people, their greatest career enemy is not risk or failure, but stasis. If you shy away from opportunity, convinced that the only risk worth taking is a single mighty one, then you’re likely stuck in the status quo. Taking a chance, even if it fails to pan out, usually gets you learning and networking more than remaining where you are. If you aren’t growing, it’s time to try something new. It turns out that consistently embracing risk-taking in your career might be the least risky move of all.


About the Author

Sukhinder Singh Cassidy is a leading technology executive and entrepreneur, board member, and investor with 25 years of experience founding and helping to scale companies, including Google, Amazon, and Yodlee. Most recently, she served as president of StubHub, which sold in 2020 for $4+ billion under her leadership. She is the founder of theBoardlist, a premium talent marketplace that helps diverse leaders get discovered for board and executive opportunities, and the author of Choose Possibility: Take Risks and Thrive (Even When You Fail) (HMH; August 17, 2021; a Wall Street Journal bestseller).