Choose Possibility

In the spring of 1993, Singh Cassidy was getting ready to launch her career. She was in her last semester of college and was eager to start the career she thought she wanted. Her goal was to become an investment banker, or perhaps a management consultant.

She applied to big firms and dreamed of success: fat paychecks, power suits, and CEOs to her left and right. But spring and summer passed, fall came, and to Singh Cassidy’s increasing despair, not a single job offer materialized.

Stuck at her parent’s home in Ontario, Canada, she watched as her former classmates set off to pursue their careers. She’d only just graduated but feared she’d already failed.

The key message here is: Free yourself from the hero’s journey and pursue multiple options at once.

Our culture thrives on heroic myths, stories where one person risks everything to vanquish a foe, prove her worthiness, and achieve her dreams. When we recall these stories, we often distill the hero’s journey into an unalterable path, forgetting that along the way, our hero faced many possibilities.

The same can be said for our careers. When you imagine that a single choice defines you, you lose sight of the numerous other options out there. You catastrophize your setbacks and let your fear of failure gain the upper hand. You may even quit.

But if, instead, you take on multiple, small risks, you’ll find you can build momentum and generate unforeseen opportunities.

Take the example of Ashvin Kumar, who founded an e-commerce start-up in 2008. Instead of pursuing a single platform, his company launched almost 20 apps within 18 months. Each app took little in terms of capital, yet having so many meant lots of room for feedback. It was a numbers game. By expanding his options, Kumar reduced his risk and maximized his opportunity. Eventually, a live auction app, called Tophatter, took off and found millions of users.

Back in 1993, a similar approach broke Singh Cassidy out of her post-college doldrums. She took a low-level job at a regional bank while pursuing several low-stakes risks: she applied to med school, passed Canada’s foreign service exam, and took a crack at the Law School Admissions Test.

Most importantly, she accepted a train ticket to New York City. In the next blink, we’ll see how putting herself in the proximity of Wall Street unlocked new possibilities.