Choose Possibility Summary

"What would you do if you weren't afraid?" This book challenges us to face that question and see risk not as a danger but as a door to new opportunities.

1. Let Go of the Hero's Journey Mindset

We often cling to the idea that success requires one bold, life-changing moment. But real achievements usually come from taking many smaller steps. Sukhinder Singh Cassidy reminds us that defining success as a single trajectory limits our potential and magnifies our fear of failure.

For instance, Singh Cassidy struggled to land her dream job after college. Instead of viewing this as a dead end, she explored multiple small opportunities, from accepting a banking position at a regional bank to taking exams for med school and law school applications. By doing so, she opened up multiple career options and reduced the pressure to "get it right" in one go.

Ashvin Kumar, the founder of an e-commerce start-up, adopted a similar approach. His company tested 20 small apps instead of relying on one big gamble. This mindset led to the success of Tophatter, a live auction app with millions of users.

Examples

• Singh Cassidy applying to diverse opportunities after struggling post-graduation.
• Ashvin Kumar's success by launching and testing 20 apps.
• The idea of pursuing multiple small risks to reduce pressure and maximize outcomes.

2. Be Present to Seize Hidden Opportunities

Opportunities are often closer than we think, but they require us to show up physically and emotionally. Singh Cassidy demonstrates that proximity to opportunities is a powerful catalyst for change. After receiving a rejection letter from Merrill Lynch, she didn’t give up. Her father encouraged her to visit New York City anyway, and this simple decision unlocked her first big career break.

Being in the right place at the right time has its rewards. Singh Cassidy later moved to San Francisco during the heights of the tech boom, a choice that fast-tracked her entry into technology leadership. Proximity often fosters chance meetings, insights, and opportunities that can’t be accessed remotely.

Careers often advance faster through these winding paths compared to a carefully planned trajectory. Whether it’s a train ticket to New York or a move to embrace the Silicon Valley scene, the act of physically showing up opens up unseen doorways.

Examples

• Accepting a New York train ticket that led to a job offer at Merrill Lynch.
• Being present in London to network and secure a critical position at British Sky Broadcasting.
• Moving to San Francisco in time to ride the tech boom wave.

3. Confront the Fear of Loss to Take Action

Our choices often feel stalled between two fears: the fear of losing what we have and the fear of missing out on what we could gain. Singh Cassidy explains that balancing these fears—and confronting them—allows us to generate momentum toward action.

For example, Singh Cassidy’s sister, Nicky, hesitated to pivot from her struggling optometry business. By naming her fears (financial loss, reputation, and the well-being of her employees), she created a set of backup plans. This made the leap feel less intimidating and allowed her to pursue healthier professional options.

The story of Alan Eustace, a Google engineer, demonstrates a similar strategy. Before jumping from the stratosphere in 2014, Eustace ran hundreds of tests for three years, ensuring every fear was addressed. Once his calculations outweighed his anxieties, his leap became a reality.

Examples

• Singh Cassidy advising her sister to unpack her fears and take small steps toward change.
• Alan Eustace preparing thoroughly for his daring space jump.
• Using contingency planning to explore risks more confidently.

4. Prioritize People Over Positions

People shape both your workday and your long-term career. Singh Cassidy highlights the importance of prioritizing colleagues over flashy titles when choosing new opportunities. She learned this lesson at OpenTV, where the lack of alignment with her boss and coworkers led to a mismatch despite the role's appeal.

At Junglee, a less glamorous company, she found her professional "tribe"—smart, motivated people with aligned goals. These relationships had lasting importance throughout her career. They offered mentorship, honest feedback, and collaboration for decades afterward.

Understanding workplace dynamics can make or break your experience. Surrounding yourself with your true professional allies can lead to learning, growth, and long-term success even in less-than-glamorous industries.

Examples

• Realizing the people fit wasn’t right at OpenTV.
• Finding a collaborative, driven team and strong mentorship at Junglee.
• Cultivating relationships that extended across decades of career changes.

5. Recognize the Role of Forces Outside Your Control

Success is never entirely within your control. External factors—both good and bad—play a significant role in the trajectory of your career. Singh Cassidy credits her rise to leadership positions to being in the right industries at the right time, such as the tech boom of the 1990s and 2000s.

Yet, adversity (headwinds) also shapes us. Singh Cassidy shares the story of Jane Fraser, Citigroup's CEO, who faced massive challenges stabilizing Latin American banking operations. While external headwinds made her job harder, they also forged her resilience and boosted her reputation.

When we acknowledge what’s in and out of our control, we release ourselves from unnecessary self-blame for failures while being fully present for the opportunities ahead.

Examples

• Recognizing the tech boom as a "tailwind" that accelerated her success.
• Drawing career lessons from Citigroup’s Jane Fraser battling external crises.
• Understanding and embracing challenges to build new skills.

6. Break Big Risks into Smaller Parts

When faced with high-stakes decisions, breaking them into digestible parts reduces their complexity. Singh Cassidy advises assessing both potential risks and gains systematically. By quantifying these, one can better handle seemingly overwhelming situations.

For instance, Singh Cassidy suggests regularly weighing opportunity factors like ambition alignment and team chemistry alongside downsides like financial losses or reputational harm. A structured approach gives clarity and confidence.

Even then, intuition should not be ignored. While logic grounds decisions, gut feelings can signal unspoken concerns. Singh Cassidy encourages balancing both for a layered understanding of big risks.

Examples

• Evaluating opportunity factors like team culture before joining Junglee.
• Rating financial risks when deciding to fund new ventures like Joyus.
• Emphasizing “two-way door” questions—can this decision quickly be reversed?

7. Rewards from Risks Are Rarely Linear

Singh Cassidy explains how risks often lead to rewards in unpredictable ways. Her time at Polyvore, for example, resulted in personal disappointment but still yielded long-term rewards like financial benefits and future career opportunities.

Life seldom rewards you directly in proportion to effort. Results from big risks might appear years later or in ways you didn’t expect. They might even help you discover new strengths or directions you’d never considered. This non-linear nature defines real growth.

By staying open to unexpected payoffs and learning from every experience, you maximize the dividends from any venture, regardless of outcome.

Examples

• Emerging with financial and network gains even after leaving Polyvore.
• Cultivating CEO skills from the ups and downs of multiple opportunities.
• Using setbacks to drive new ventures like Joyus.

8. Learn, Persist, and Exit Gracefully When Needed

Failure provides fertile ground for growth. Singh Cassidy reflects upon her journey with Joyus, a multiyear project full of innovation and effort that nevertheless fell short of sustainable profitability. Even so, it taught her invaluable lessons, especially about balancing competing objectives in business.

While persisting is important, knowing when to leave is equally key. Singh Cassidy advises exiting with grace, offering continued effort until your last day and ensuring your team thrives in your absence. This approach preserves relationships and keeps doors open.

Success follows those who create opportunities even in transition and never burn bridges unnecessarily. Timing, self-awareness, and generosity matter deeply.

Examples

• Learning from conflicting goals in Joyus’s business model.
• Persisting despite early failure at OpenTV, which led to new roles.
• Ending poorly suited roles with care to preserve networks.

9. Power Is Found in Helping Others

True power stems from empowering those around you. Singh Cassidy’s launch of theBoardlist exemplifies this perspective. By connecting qualified women with leadership opportunities, she turned systemic barriers into a platform for growth across the industry.

This lesson extends to small, everyday interactions. Whether it’s championing someone’s talent, offering mentorship, or sharing networks, lifting others amplifies your impact far beyond your immediate success.

Her father’s philosophy also shaped this view. His simple yet profound encouragement motivated others to achieve things they never thought possible. From grand initiatives to quiet support, power derived from shared growth is enduring and limitless.

Examples

• Launching theBoardlist to elevate women into tech boardrooms.
• Giving others vital encouragement during mentoring moments.
• Applying leadership principles learned from her father to impact communities.

Takeaways

1. Actively seek opportunities to step outside your comfort zone daily. These small risk actions will build the resilience and skills you need for bigger decisions.
2. Always show up—physically and mentally—where opportunities may arise. Proximity to people and events is key to recognizing hidden possibilities.
3. Share power and opportunities with others. Whether it’s mentoring, recommending, or creating roles, collaborative growth has lasting rewards for all involved.