In her book "Choose Possibility," Sukhinder Singh Cassidy offers a fresh perspective on risk-taking and career development. Drawing from her extensive experience as a tech executive and entrepreneur, Singh Cassidy challenges common misconceptions about risk and provides practical strategies for embracing uncertainty to unlock new possibilities.
Introduction
We often think of risk as something to be avoided, especially when it comes to our careers. We fear that one wrong move could lead to financial ruin or irreparable damage to our reputation. However, Singh Cassidy argues that this view of risk is fundamentally flawed. Instead of seeing risk as a series of make-or-break moments, we should recognize it as an ongoing state of uncertainty and promise.
Throughout the book, Singh Cassidy shares personal anecdotes, case studies, and actionable advice to help readers reframe their understanding of risk and learn how to harness its power to create opportunities. By adopting a more nuanced approach to risk-taking, we can free ourselves from the constraints of the traditional "hero's journey" narrative and open ourselves up to a world of possibilities.
Embracing Multiple Possibilities
One of the key ideas in "Choose Possibility" is the importance of pursuing multiple options simultaneously. Singh Cassidy illustrates this concept through her own post-college experience. After graduating, she found herself stuck at her parents' home in Ontario, Canada, without a job offer in sight. Instead of fixating on a single career path, she took a low-level job at a regional bank while simultaneously exploring other options:
- Applying to medical school
- Passing Canada's foreign service exam
- Taking the Law School Admissions Test
This approach of pursuing multiple low-stakes risks allowed her to keep her options open and eventually led to unexpected opportunities. Singh Cassidy emphasizes that by expanding our options, we can reduce overall risk and maximize our chances of success.
The author shares the story of Ashvin Kumar, who founded an e-commerce start-up in 2008. Instead of focusing on a single platform, Kumar's company launched nearly 20 apps within 18 months. This strategy allowed for rapid feedback and increased the chances of finding a successful product. Eventually, one of the apps, Tophatter, took off and found millions of users.
The Power of Proximity
Another crucial lesson from the book is the importance of physical presence in creating opportunities. Singh Cassidy's journey from rural Ontario to Wall Street illustrates this principle perfectly. After receiving a rejection letter from Merrill Lynch that included an invitation to visit their office in New York City, Singh Cassidy's father recognized the hidden opportunity and bought her a train ticket on the spot.
This decision proved to be a turning point in her career. The informal tour at Merrill Lynch led to a brief interview, which in turn resulted in an invitation to a full-day tryout for an analyst position. A month later, she aced the tryout and landed the job.
The lesson of proximity and opportunity continued throughout Singh Cassidy's career:
- Moving from New York to London to work with British Sky Broadcasting
- Relocating to San Francisco during the tech boom of the late 1990s
Each move brought her closer to new opportunities and allowed her to build a valuable professional network. Singh Cassidy emphasizes that being physically present in the right place at the right time can unlock possibilities that might otherwise remain hidden.
Balancing Fear of Loss and Fear of Missing Out
One of the most insightful aspects of "Choose Possibility" is its exploration of the two competing fears that influence our decision-making: fear of loss and fear of missing out (FOMO). Singh Cassidy argues that to take meaningful risks, we must learn to balance these two fears.
The author shares the story of her sister Nicky, who was struggling to save her failing optometry business. Nicky was paralyzed by her fear of loss – the potential financial losses, the loss of her patient community, and the impact on her employees. To help her sister move forward, Singh Cassidy outlines a process for confronting and managing fear of loss:
- Name your worries: Identify specific concerns and quantify potential losses.
- Consider the long-term perspective: How will these problems look in three months, three years, or ten years?
- Assess the reversibility of decisions: Can the damage be undone?
- Develop contingency plans: Prepare for potential negative outcomes.
By working through these steps, Nicky was able to overcome her fear of loss and ultimately make a career change that improved her quality of life.
Singh Cassidy also shares the story of Alan Eustace, a 58-year-old Google engineer who jumped to Earth from the stratosphere in 2014. Eustace spent three years meticulously planning and testing his equipment, addressing every potential risk. By thoroughly preparing and facing his fears head-on, Eustace was able to shift the balance from fear of loss to fear of missing out on a once-in-a-lifetime opportunity.
The Importance of People in Career Decisions
While pursuing interesting work is a natural goal, Singh Cassidy emphasizes the critical role that colleagues play in our ultimate success or failure. She learned this lesson the hard way during her time at OpenTV, where her intense work style clashed with the company culture.
The author advises readers to prioritize people when evaluating career moves:
- Look for inspiring coworkers who can turn even mundane tasks into exciting challenges.
- Seek out mentors and teachers who are invested in developing talent.
- Build relationships with colleagues who can provide honest, constructive feedback.
- Cultivate friendships with people who understand and support your ambitions.
Singh Cassidy's experience at Junglee, where she found her "professional tribe," highlights the positive impact of working with like-minded, passionate individuals. These relationships not only enhanced her immediate work experience but also played a crucial role in her career development for years to come.
Understanding External Factors and Self-Knowledge
"Choose Possibility" emphasizes the importance of recognizing factors beyond our control that influence our success or failure. Singh Cassidy credits much of her early success to the tailwind of the late 1990s and early 2000s tech boom. She cautions against attributing success or failure solely to individual abilities, as this can lead to an inaccurate and potentially harmful self-assessment.
The author introduces the concept of headwinds and tailwinds in career development:
- Tailwinds: Favorable conditions that can propel careers forward, such as economic booms or emerging industries.
- Headwinds: Adverse forces that can hinder progress, like economic downturns or industry disruptions.
Singh Cassidy argues that while fighting against headwinds can be challenging, these experiences often provide unique opportunities for professional growth. She cites the example of Jane Fraser, Citigroup's first female CEO, who navigated significant challenges during the subprime mortgage crisis and earned a reputation for resilience and adaptability.
To effectively navigate these external factors, Singh Cassidy stresses the importance of self-knowledge. She advises readers to:
- Examine their passions, talents, and values
- Seek honest feedback from mentors and trusted colleagues
- Acknowledge weaknesses and work on improving them
- Regularly assess whether their current role aligns with their strengths and goals
By combining an understanding of external factors with deep self-knowledge, individuals can make more informed decisions about when to persist in the face of challenges and when to move on to new opportunities.
Deconstructing Big Risks
While "Choose Possibility" emphasizes the value of taking small, frequent risks, Singh Cassidy acknowledges that some decisions – such as a mid-life career change or relocation – involve higher stakes. To address these situations, she provides a framework for deconstructing and evaluating big risks:
- Break down the potential costs and opportunities
- Rate each element of the opportunity:
- Potential to fulfill ambitions
- Fit with personal strengths, weaknesses, and values
- Influence of headwinds and tailwinds
- Quality of people involved
- Assess the downsides:
- Potential financial harm
- Impact on reputation or ego
- Personal losses
- Consider the reversibility of the decision
- Develop a recovery plan
By methodically evaluating these factors, individuals can arrive at an overall "risk score" and "opportunity score" to inform their decision-making process.
Singh Cassidy also emphasizes the importance of listening to one's intuition while still subjecting gut feelings to scrutiny. She advises readers to balance instinct with data-driven analysis to make well-rounded decisions.
The Nonlinear Relationship Between Risk and Reward
One of the most valuable insights in "Choose Possibility" is the recognition that risk and reward often have a nonlinear and unpredictable relationship. Singh Cassidy illustrates this concept through her experience as CEO of Polyvore, a fashion-focused e-commerce platform.
Despite losing the job due to conflicts with the company's founder, Singh Cassidy's time at Polyvore yielded unexpected benefits:
- A financial windfall when the company was sold to Yahoo
- Increased attention from other companies due to her strong performance
- Valuable experience that informed the creation of her own online shopping platform, Joyus
The author emphasizes that the results of taking risks are often widespread and may appear at unpredictable times. A setback in one area might lead to new professional connections, knowledge gained, or investment opportunities in another.
Singh Cassidy encourages readers to embrace this nonlinear nature of risk and reward by:
- Pursuing multiple options simultaneously
- Remaining open to unexpected opportunities
- Focusing on professional growth during periods of uncertainty
- Putting passion into all aspects of a project, even those that seem mundane
- Seeking to understand and address persistent problems
By adopting this mindset, individuals can maximize their learning and growth potential, even when immediate results are not apparent.
Learning from Failure and Moving On Gracefully
"Choose Possibility" devotes significant attention to the importance of learning from failure and knowing when to move on. Singh Cassidy shares her experience with Joyus, her fashion commerce start-up that struggled to balance revenue against production costs despite years of hard work and small successes.
The author emphasizes several key lessons from this experience:
- Recognize the challenges of balancing multiple large goals
- Avoid mistaking busyness for impact
- Remain open to feedback and address weaknesses
- Confront difficult underlying problems rather than avoiding them
Singh Cassidy advises readers to continually reassess their fit with current challenges using the framework outlined earlier in the book. If impact and learning opportunities plateau, it may be time to seek new challenges.
When deciding to move on from a role or project, the author offers several tips for maximizing the transition:
- Maintain maximum effort until the last day
- Set up colleagues for success
- Share learned insights and knowledge
- Leave things in good order
- Avoid lingering once work is complete
By following these guidelines, individuals can preserve professional relationships and potentially create new opportunities even as they move on to new challenges.
The Power of Generosity and Choice
In the final sections of "Choose Possibility," Singh Cassidy explores the concept of power and how it relates to choice and generosity. She shares her experience founding theBoardlist, a talent marketplace that connects women with leadership positions in the tech industry.
Through this project, Singh Cassidy discovered that true power comes from creating opportunities for others. She emphasizes that the most influential leaders are those who allow their power to flow to those around them.
The author encourages readers to cultivate their own power through acts of generosity, both large and small:
- Offering words of encouragement
- Writing letters of recommendation
- Sharing the spotlight with others
- Creating opportunities for those with less access or influence
Singh Cassidy argues that this form of power is renewable and cannot be taken away because it comes from within. By choosing possibility and sharing it with others, individuals can create ongoing cycles of growth and opportunity.
Conclusion
"Choose Possibility" offers a refreshing and practical approach to risk-taking and career development. Singh Cassidy's insights challenge readers to reframe their understanding of risk and embrace it as a tool for growth and opportunity.
Key takeaways from the book include:
- Pursue multiple options simultaneously to reduce overall risk and maximize opportunities
- Recognize the power of physical proximity in creating chances for success
- Balance fear of loss with fear of missing out to make informed decisions
- Prioritize people and relationships in career choices
- Understand the influence of external factors while maintaining self-knowledge
- Deconstruct big risks to make more informed choices
- Embrace the nonlinear relationship between risk and reward
- Learn from failure and know when to move on gracefully
- Cultivate power through generosity and creating opportunities for others
By internalizing these lessons and putting them into practice, readers can develop a more nuanced and effective approach to risk-taking in their personal and professional lives. Singh Cassidy's book serves as a valuable guide for anyone looking to unlock new possibilities and achieve greater success in an uncertain world.
As a final piece of actionable advice, Singh Cassidy encourages readers to make a habit of taking small risks daily. Following Eleanor Roosevelt's advice to "Do one thing every day that scares you," individuals can build momentum, learn from both successes and failures, and gradually become stronger and braver. This practice of accumulating small acts of courage will prepare them for larger, more audacious leaps when the opportunities arise.
In essence, "Choose Possibility" is a call to action for readers to embrace uncertainty, cultivate resilience, and actively seek out new opportunities. By adopting this mindset and implementing the strategies outlined in the book, individuals can transform their approach to risk and unlock a world of possibilities in their personal and professional lives.