What is the main message of Choose Possibility?

The main message of Choose Possibility is to embrace uncertainty and create a future filled with endless opportunities.

How long does it take to read Choose Possibility?

The reading time for Choose Possibility varies depending on the reader's speed. However, the Blinkist summary can be read in just 15 minutes.

Is Choose Possibility a good book? Is it worth reading?

Choose Possibility is a thought-provoking and inspiring read. It offers valuable insights and practical guidance to navigate through life's uncertainties.

Who is the author of Choose Possibility?

The author of Choose Possibility is Sukhinder Singh Cassidy.

Choose Possibility Summary of Key Ideas and Review | Sukhinder Singh Cassidy

Name: Choose Possibility
Rating: 4.5 (121 reviews)
Author: Sukhinder Singh Cassidy

Introduction

What’s in it for me? Learn to embrace risk and unlock possibility.

Humans suffer from a fundamental misconception of risk.

Too often, we think only of the moves that promise to define our lives, and when we think of life-altering choices, risk becomes forbidding, foreboding, even terrifying. We fear that one bad choice could bankrupt us or destroy our reputations.

But, true make-or-break moments are rare, and if you look closer, you see that they’re often made up of many smaller risks, moments that pose questions. Should you, for example, speak up in that meeting, or perhaps return that recruiter’s call?

Risk is an evolving state of uncertainty and promise. These blinks will show you how to embrace it with intelligence and generosity. And help you to see that when you choose possibility, you can make your own opportunities.

In these blinks, you’ll learn

how to handle the headwinds and tailwinds of your career;
how to balance your fear of failure against your fear of missing out; and
a better, more generative way to think about power.

Key idea 1 of 9

Free yourself from the hero's journey and pursue multiple options at once.

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.

Key idea 2 of 9

Fortune favors the physically present.

It was one evening during her post-college year at her parents’ house when Singh Cassidy got her big break: a rejection letter in the mail. She’d gotten many. But this particular one was from the megabank Merrill Lynch, and it politely closed with an invitation to visit the firm in New York City.

Singh Cassidy took the invitation as a bit of pro forma kindness. A balm for the sting of rejection. But her father read it differently.

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Key idea 3 of 9

To get momentum and take the leap, you must face your fear of loss.

Singh Cassidy’s sister Nicky was in trouble. She was working late into the night, every night, trying to save her once-thriving optometry business.

Her practice was in a shopping mall, and foot traffic was low. Local competitors were cropping up, and online retailers had begun undercutting her prices.

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Key idea 4 of 9

When evaluating whether to make a career move, tip the scales in favor of people.

When Singh Cassidy left Merrill Lynch and went to work under British Sky Broadcasting’s founders, Sam Chisholm and David Chance, she’d found men with the entrepreneurial passion to bring a dream to fruition.

That passion was contagious, so when looking for her next career move, Singh Cassidy decided that she wanted to get in on the ground floor of an innovative entertainment company. In 1997, she accepted a management position at OpenTV, a California-based interactive television startup.

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Key idea 5 of 9

Know yourself and know what’s out of your control.

At Junglee, Singh Cassidy worked as a manager before moving to build her own start-up, Yodlee, that sold for a large profit to Amazon. She subsequently launched her own tech company, which also sold for big money, and then joined Google, getting Google Maps off the ground and becoming one of its highest-ranking executives.

As relentlessly driven as she was throughout this meteoric rise, Singh Cassidy credits much of her good fortune to a historic tailwind: the tech boom of the late 1990s and early 2000s.

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Key idea 6 of 9

The tools you’ve honed on smaller risks can be combined to unpack bigger ones.

Let’s take a minute to step back and review what we’ve learned so far. We’ve learned to value proximity and being in reach of our goals, and the people that come along with them. We’ve also learned to value self-knowledge, as well as the circumstances beyond our control. Most importantly, we’ve learned that risk isn’t a single, life-altering choice, but an ongoing practice.

But then again, some risks – such as a mid-life career change or a move across the country – are undeniably large. The stakes are high. So, what should you do in these situations?

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Key idea 7 of 9

Risk and reward have a nonlinear and often unpredictable relationship.

When Singh Cassidy took on her first CEO gig, it was a move that she made with some trepidation. The job was at Polyvore, a fashion-focused e-commerce platform, and she knew that she’d be working alongside Polyvore’s founder. In other words, she was being asked to run the company while the man who’d created and run it to that point was right beside her.

She set up regular coffee dates with the founder in order to build a rapport of honesty and respect. But sure enough, a schism opened between them. Their visions for Polyvore simply didn’t match, and when the crisis came to a head, Singh Cassidy found herself out of a job.

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Key idea 8 of 9

Learn from failure and, when the time comes, move on in a way that will create more opportunity.

Singh Cassidy’s fashion commerce start-up Joyus had a wild ride. She assembled a first-rate team, attracted millions of dollars from investors and patented an e-commerce video player. The videos were the start-up’s principal feature. Produced in-house, they were sleek and beautiful, and, unlike other shopping videos, they were interactive and allowed users to buy the products.

The videos were also costly to make. Despite doubling revenues every year, Joyus couldn’t balance those revenues against the cost of production. After six years, Joyus sold to another company.

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Key idea 9 of 9

Power comes from choice and generosity.

In 2015, Singh Cassidy opened her Rolodex and started reaching out to other women who, like her, were tech leaders. She had a project in mind.

The industry was roiling with debate over gender and equity. Singh Cassidy knew that women were thriving in tech in spite of the bias and harassment they faced, but she’d long noticed that one realm of power remained closed to them: the boardroom.

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