Choose Possibility
Seek Change, Take Risk, and Thrive (Even When You Fail)
Book Edition Details
Summary
Choices shape our destinies, but what happens when those choices go awry? In "Choose Possibility," acclaimed Silicon Valley pioneer Sukhinder Singh Cassidy invites you into her world of high-stakes decisions and unforeseen detours. Unpacking her nonlinear journey, she shares the secrets behind transforming missteps into momentum. This isn't about a single leap of faith; it's about mastering the art of risk through a series of smart, strategic moves. Singh Cassidy's insights, from the myths of success to making FOMO your ally, redefine how we view professional gambles. Ready to rethink risk and unlock your potential? This is your guide to embracing uncertainty with confidence and clarity.
Introduction
What if the very thing you fear most is actually the key to unlocking your greatest potential? In our rapidly changing world, many of us find ourselves trapped by the illusion that safety lies in staying still, in avoiding risks, in maintaining the status quo. We've been conditioned to believe that risk-taking is reserved for the boldest among us, that it requires superhuman courage, or that one wrong move could derail everything we've worked for. But this couldn't be further from the truth. The reality is that the biggest risk we face isn't failure from taking chances—it's the risk of never reaching our full potential by playing it too safe. Every day, opportunities pass us by while we wait for the "perfect" moment, the complete plan, or the guarantee of success that will never come. Yet those who thrive in today's dynamic world have learned a different truth: that possibility isn't scarce, but abundant, and that power comes not from avoiding uncertainty, but from learning to navigate it skillfully. They understand that choosing possibility isn't about making one perfect leap, but about developing the muscle to take smart risks consistently, to learn from every outcome, and to keep moving forward regardless of setbacks.
Get Going: Start Taking Smart Risks
The foundation of choosing possibility lies in understanding that risk-taking isn't about making one monumental, life-altering decision. Instead, it's about developing the habit of taking many smaller, calculated risks that compound over time into extraordinary results. This approach transforms risk from a terrifying leap into the unknown into a learnable skill that anyone can master. Consider the story of Alyssa Nakken, who became Major League Baseball's first full-time female coach. Her journey began not with a grand plan to break barriers in professional sports, but with a simple recognition that she felt unfulfilled in her stable financial planning job. Rather than quit immediately to pursue an undefined dream, Nakken took her first small risk: she enrolled in a graduate sports management program while working to support herself. This led to a series of internships with different organizations, each teaching her something new about the industry and about herself. What made Naknen's approach so effective was her willingness to keep experimenting without knowing exactly where she was headed. She knocked on doors, asked for informational interviews, and put herself in proximity to the opportunities she wanted to explore. When the San Francisco Giants offered her an internship, she didn't wait to feel perfectly qualified—she said yes and figured it out as she went. Each role led to the next, building her expertise and network until the opportunity to make history presented itself. The path to developing your risk-taking muscles starts with reframing how you think about uncertainty. Begin by identifying small opportunities in your current environment where you can stretch beyond your comfort zone. This might mean volunteering for a project that challenges you, reaching out to someone in your field for advice, or simply speaking up in a meeting with a new idea. The key is to start before you feel ready, to embrace the learning that comes from both successes and failures, and to maintain momentum through consistent action rather than perfect planning.
Get Smarter: Build Your Risk-Taking Intelligence
Smart risk-taking isn't about being fearless—it's about being strategic. The most successful risk-takers have learned to evaluate opportunities not just based on their potential upside, but by carefully considering the people, timing, and circumstances that will determine their success. They understand that who you work with often matters more than what you work on, and that external forces can either amplify or undermine even your best efforts. The story of Nick Grudin's career evolution perfectly illustrates this principle. Starting as a journalist at small-town newspapers, Grudin could have stayed on a traditional media track. Instead, he paid attention to the changing landscape around him and noticed how technology was disrupting his industry. Rather than resist this change, he chose to position himself at its center. During graduate school, he took an internship at the Washington Post working not as a journalist, but on the business side, helping the newspaper adapt to the digital age. This strategic pivot led Grudin to discover unexpected strengths in business analysis and strategy while still honoring his passion for media. When he later joined Google and eventually Facebook, he didn't abandon his journalism background—he leveraged it to build bridges between traditional media companies and emerging technology platforms. His success came not from having a perfect plan, but from remaining alert to changing conditions and positioning himself to benefit from major industry trends. To build your own risk-taking intelligence, start by developing a deeper understanding of yourself—your natural strengths, core values, and areas for growth. Conduct honest self-assessments and seek feedback from trusted colleagues about how others perceive your capabilities. Simultaneously, become a student of the forces shaping your industry and the broader economy. Look for emerging trends that could create new opportunities or threaten existing ones. Most importantly, surround yourself with people who share your values but bring different skills and perspectives to complement your own weaknesses.
Get Rewarded: Turn Risks Into Career Success
The ultimate reward of choosing possibility isn't any single achievement, but the accumulation of capabilities, experiences, and relationships that compound over time into extraordinary career capital. The most successful risk-takers understand that growth happens in cycles—periods of challenge and learning followed by integration and success, repeated throughout their careers at increasingly higher levels. This cyclical nature of growth is beautifully illustrated in the journey of Stacy Brown-Philpot, who rose from modest beginnings in Detroit to become CEO of TaskRabbit and one of the most prominent leaders in technology. Her career wasn't a straight line to the top, but a series of calculated risks that each built upon the last. After leaving a secure position at Goldman Sachs, she joined Google when it was still a relatively small company with an uncertain future. The risk paid off, but rather than rest on her success, Brown-Philpot continued to challenge herself. When Google offered her the opportunity to move to India to run operations there, she faced a difficult choice. The role would separate her from her husband and thrust her into an unfamiliar cultural environment. However, she recognized that the experience would force her to develop new leadership capabilities and gain international experience that few of her peers possessed. The India assignment transformed her from a competent manager into an inspirational leader, preparing her for the CEO roles that would follow. The key to getting rewarded for your risks lies in maintaining a long-term perspective while focusing on short-term impact. Instead of fixating on any single outcome, concentrate on consistently delivering value in whatever role you're in while building the relationships and capabilities that will create future opportunities. Document your successes, learn from your failures, and always be preparing for the next challenge. Remember that the most valuable currency in today's economy isn't any particular skill or achievement, but your ability to adapt, learn, and create value in new and changing circumstances.
Summary
The journey of choosing possibility isn't about becoming fearless—it's about becoming skillful in the art of navigating uncertainty while building the life and career you truly want. As this exploration has shown, the process of smart risk-taking is learnable, repeatable, and available to anyone willing to start where they are with what they have. The key insight is beautifully captured in one of the book's central truths: "All life is an experiment. The more experiments you make the better." This perspective transforms everything. Instead of waiting for the perfect opportunity or complete certainty, you can begin immediately to conduct small experiments in your own life. Each choice you make, whether it succeeds or fails, provides valuable data for your next decision. Each relationship you build expands your network of possibilities. Each challenge you overcome increases your capacity for future growth. The compound effect of these accumulated experiences creates a form of career capital that becomes increasingly valuable over time. Your next step is simple but powerful: identify one small risk you can take this week that moves you in the direction of something you want to explore or achieve. It doesn't have to be perfect or permanent—it just has to be a step forward. Whether that's sending an email, having a conversation, or volunteering for a new assignment, choose possibility today and begin building the momentum that will carry you toward the future you envision.
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By Sukhinder Singh Cassidy
