Choose Possibility

Choose Possibility Plot Summary

Introduction

When was the last time you found yourself at a career crossroads, paralyzed by the fear of making the wrong move? Perhaps you've dreamed of starting a business, changing industries, or raising your hand for that challenging project—but something held you back. That something is often our misunderstanding of risk itself. We've been conditioned to view risk-taking as a single momentous leap that will either make or break us, when in reality, successful professionals approach risk very differently. The truth is that risk-taking is not about one dramatic, life-altering choice but rather a series of deliberate decisions and actions taken over time. It's about consistently choosing possibility, even in small ways, and understanding that each step builds your risk-taking muscles while unlocking new opportunities. Throughout this journey, you'll discover that the most successful people aren't necessarily those who never fail but those who learn to navigate through both successes and failures with agility, resilience, and an unwavering commitment to growth. The pages ahead will transform how you view risk, showing you practical ways to embrace possibility in your career and life.

Chapter 1: Ditch the Hero's Journey: Small Risks Lead to Growth

At its core, the "hero's journey" myth suggests that career success comes from a single, dramatic risk—a grand leap into the unknown that either results in triumph or catastrophe. This misconception can be paralyzing, making us believe that everything rides on one high-stakes decision. In reality, career growth emerges from a series of smaller risks taken consistently over time. Nicky's story perfectly illustrates this principle. As an optometrist running her own practice in a suburban mall, she found herself in a challenging situation. Mall foot traffic was declining, competition was intensifying, and more customers were buying glasses online. Her long hours—often arriving home at 10 p.m. to care for her two sons—combined with diminishing profits left her exhausted and stressed. Despite this deteriorating situation, Nicky couldn't bring herself to make a change. "I took a super big risk in buying and building out this practice," she explained. "Sure, I could make a change, but going to work for someone else might be an even bigger mistake. I'd be giving up everything I've built." Nicky was trapped by the Myth of the Single Choice—the belief that one decision would determine her entire future. This perspective prevented her from seeing that she could approach her situation through a series of smaller moves rather than one dramatic pivot. After months of discussions and spreadsheet analysis of her options, Nicky finally took her first small risk: renegotiating her lease to switch from long-term to month-to-month, creating flexibility for future moves. This initial step, though modest, was crucial in breaking her paralysis. Two years later, Nicky took another step by pausing her practice to evaluate new options. Rather than seeing this as an all-or-nothing move, she viewed it as part of a process. This openness allowed serendipity to play its role. A friend told her about a new medical clinic opening closer to her home that was seeking optometrists. Nicky interviewed and secured a lucrative contract that let her work closer to home, maintain reasonable hours, and continue serving her patients with more comprehensive services. The key to navigating career transitions is recognizing that most successful people don't make a single heroic leap. Instead, they piece together smaller and larger choices over time to unlock new possibilities. Research supports this approach: a LinkedIn study of hundreds of thousands of professionals found that those with diverse experiences advance more quickly than specialists, leading to the observation that "the quickest path is a winding one" for those seeking top positions. To implement this strategy in your own career, start by identifying small steps you can take right now, rather than waiting for perfect clarity or the "right moment" for a big move. Create options through multiple small risks that build momentum while minimizing exposure. Remember that inaction itself is often the riskiest choice of all—when you're not growing, you're likely falling behind. As you embrace this series of smaller choices, you'll find that your capacity for productive risk-taking grows along with your confidence.

Chapter 2: Pipeline in Parallel: Pursue Multiple Opportunities

Pipelining in parallel means pursuing multiple options simultaneously rather than committing to a single path. This approach lets you gather information, test possibilities, and keep doors open while minimizing the overall risk of any one choice. Instead of putting all your eggs in one basket, you create a diversified portfolio of career opportunities. Consider my own experience as a recent university graduate searching for my first job. While my peers had secured prestigious positions at investment banks and consulting firms, I had missed campus recruiting season and found myself scrambling for interviews. After several rejections from top firms, I reluctantly accepted a position at TD Bank in Toronto. However, I didn't stop there. When my friend Bertram suggested I send my resume to Merrill Lynch in New York—despite the firm not recruiting at Canadian universities—I took the chance. Their response was lukewarm: I'd be welcome for an "informational interview" if I was "ever in New York." Many would have seen this as a polite rejection, but my father encouraged me to take a train to New York and follow up. This small risk paid off unexpectedly—my fifteen-minute informational interview turned into a full day of meetings, culminating in an invitation to their final selection round. While preparing for this opportunity, I continued pipelining, applying to the Canadian Foreign Service, medical school, and law school. This parallel pursuit of options wasn't about desperation but about creating multiple pathways to discover what might work best. Entrepreneurs often use this approach to great effect. Ashvin Kumar, founder of the marketplace Tophatter, recounts how he and a partner quit their jobs in 2008 to start a technology company. Rather than putting all their energy into one product, they developed fifteen to twenty different ideas over eighteen months. "We didn't really know what we were going to build," he explains. "We sort of leveraged that enjoyment and said, 'Look, let's not worry too much about what exactly we're building.'" This exploration eventually led to Blippy, which attracted millions in funding, and later to the successful launch of Tophatter. To implement pipelining effectively, first create your own timeline for discovery rather than reacting to everyone else's schedule. When opportunities come faster than expected, resist the pressure to decide quickly. Instead, clarify your own timeline for exploring choices and communicate it diplomatically to others. Second, if you're trying to escape an unpleasant situation, separate your "downside scenario" (what happens if you stay put) from your "upside opportunity" (what you'd pursue in ideal circumstances). This distinction helps you identify more options aligned with each goal. Another powerful tactic is finding a brainstorming buddy—someone who understands your ambitions and can help generate possibilities without judgment. This person might not be your best friend or partner but rather someone with complementary perspectives who can enhance your thinking. Finally, embrace passive pipelining by staying open to opportunities even when you're not actively seeking change. Some of the best career opportunities come from simply accepting invitations to connect with interesting people regardless of immediate relevance. By pursuing multiple paths simultaneously, you gain more information faster, build momentum toward change, and develop the conviction needed to make a bigger choice when the time comes. This approach isn't about indecision—it's about making more informed decisions by exploring multiple possibilities before committing to one direction.

Chapter 3: Value People Over Passion When Taking Risks

When making career decisions, we often prioritize the "what"—finding work we're passionate about in industries that excite us. However, research and experience show that the "who" you work with matters far more for career advancement and satisfaction. The people around you significantly influence your learning, opportunities, and overall trajectory. My own career illustrates this principle clearly. After leaving Merrill Lynch, I joined a startup called OpenTV. Though excited about entering the interactive TV industry, I quickly encountered challenges with my boss. He told me I was "scaring the secretaries" and gave the most interesting work to a male colleague with a volatile style. Despite raising concerns, the situation didn't improve. Feeling undervalued, I was receptive when a recruiter called about a product manager role at Junglee, a tech company whose tagline—"The Internet Is the Database"—initially seemed boring compared to entertainment. During interviews at Junglee, I was impressed by founder Venky Harinarayan's intelligence and straightforward style. His co-founders and the company's president Ram Shiriram were equally impressive—smart, candid, and hungry to succeed. Upon joining, instead of facing resistance, I found immediate trust. On my second day, they asked if I'd switch from product management to business development to help launch a new e-commerce service. Rather than being told to "tone down," I was encouraged to leverage my strengths immediately. Over the next months, I built partnerships that caught Amazon's attention, leading to Junglee's acquisition for $280 million. The Amazon stock I received made me a millionaire in my twenties. Great people accelerate your career in four distinct ways. First, through osmosis—simply observing and emulating those with desirable skills. Second, through active challenges—being pushed to attempt things you've never done before, with support when needed. Third, through coaching—receiving consistent feedback and development. And fourth, through social learning—interacting with diverse, skilled teams assembled by great leaders. Working with exceptional people also creates a powerful network effect. When my Junglee colleagues later became investors in other startups, they opened doors for me, including the opportunity to co-found my own company, Yodlee. Years later, Ram Shriram (Google's first angel investor) helped connect me with Google's business leadership, leading to my next career chapter there. To identify great leaders worth following, look for three key signals. First, examine the company they keep—true talent magnets attract and retain smart, confident, diverse teams. Second, assess their strengths relative to yours—the best mentors have capabilities you admire but lack, creating complementary relationships. Third, determine whether their values align with yours, as shared values foster deeper understanding and respect. Implementing this approach means being deliberate about evaluating the people you'd work with when considering new opportunities. During interviews, ask questions about leadership style, team dynamics, and organizational values. Speak with current and former team members when possible. Remember that while passion for the subject matter might fade or evolve, the impact of working with exceptional people who bring out your best is enduring. By valuing who over what, you'll not only accelerate your learning but build relationships that continue opening doors throughout your career.

Chapter 4: Analyze Your Fears to Boost Confidence

Fear often prevents us from taking risks, even when we clearly see the potential benefits. Understanding the relationship between different types of fears is crucial for moving forward. The key lies in a simple equation: When our fear of missing out (FOMO) exceeds our fear of failure (FOF), we take action. Otherwise, we remain paralyzed. This dynamic played out during my consideration of leaving London for California. Though employed at British Sky Broadcasting, I felt underutilized and increasingly drawn to entrepreneurial opportunities in Silicon Valley. My FOMO regarding the booming tech industry outweighed my FOF about finding work in a new location. With savings, supportive parents, and confidence from prior successes, I resigned and moved—a decision that ultimately launched my tech career. To manage fear effectively, we must first understand that conventional wisdom about positive thinking isn't enough. Professor Gabriele Oettingen's research shows that positive thinking alone often "impeded people in the long term from moving ahead. People were quite literally dreaming themselves to a standstill." Instead of just visualizing success, we need strategies to address our fears directly. The first powerful technique is imagining the "choice-after-the-choice." By contemplating what you would do if a risk doesn't work out, you realize that few decisions are truly irreversible. For example, if you leave a large company for a startup that doesn't work out, you might return to your former employer or find a similar role elsewhere. Identifying these backup plans diminishes the perceived magnitude of risk. Second, name and size your fears precisely. There are generally three types of risks in career decisions: financial (losing money), reputational/ego (damaging your image), and personal (sacrificing joy or family time). By separating these risks and evaluating each individually, you can address them more effectively. Ego risk—fear of looking foolish or incompetent—is often the most powerful deterrent, yet it exists primarily in our own minds. Third, size your risks relative to your current situation. A choice that might be devastating for someone with limited resources could be merely uncomfortable for someone with substantial savings or strong professional connections. Understanding your personal room for failure helps you assess risks more accurately. Fourth, plan more for downside than upside. Expert negotiators focus intensely on what could go wrong before a deal is signed. Similarly, when taking risks, you should invest more energy in planning for potential failures than successes. Alan Eustace, who set the world record for highest-altitude free fall jump despite no previous experience with such stunts, spent three years meticulously testing equipment and procedures. "We probably ran two hundred and fifty tests," he explains, "the vast majority of them unmanned but some of them manned... to be able to buy down the risk the entire time." Perhaps counterintuitively, experiencing failure often makes future risk-taking easier. Entrepreneur Ade Olonoh, who built successful companies Formstack and Formspring, found that surviving business setbacks fundamentally changed his relationship with risk. "The time horizon is truly long," he reflects, "whereas early in my career it probably felt like every decision I made that ended in failure was going to wreck the rest of my career." To implement these strategies, create a simple spreadsheet listing potential risks and mitigation plans for any significant decision. Rate each fear's severity and likelihood, then identify specific actions you could take if things don't work out. This process transforms vague anxieties into manageable challenges, helping FOMO overtake FOF and enabling forward movement. Remember, fear never disappears entirely—but with these techniques, it need not prevent you from choosing possibility.

Chapter 5: Create Impact to Build Career Capital

Success in any career journey isn't just about making big leaps—it's about consistently delivering results through smaller, meaningful actions that compound over time. Impact, defined as producing significant or major effects, is the currency that builds your professional reputation and creates future opportunities, regardless of whether your original goal succeeds perfectly. Simon Chen's story at Joyus exemplifies this principle. Despite graduating from UC Berkeley with stellar grades, Simon struggled to find his first full-time job. He eventually applied for an entry-level executive assistant position supporting me (as CEO) and our chief merchandising officer. Though I was initially skeptical about hiring a recent graduate for this role, Simon impressed us immediately with his enthusiasm and work ethic. He approached even mundane tasks—managing calendars, ordering office groceries—with genuine passion, automating repetitive work while handling important communications personally. Simon constantly sought to learn about the business, asking thoughtful questions about meetings and company strategy. "Right out of college, it wasn't about chasing a fancy title. It's about what can I learn and who can I learn from," Simon explains. He found meaning in seemingly boring tasks: "One person's point of view can be, 'This is such a boring job, an office manager.' The other person's point of view can be, 'Hey. I actually get to affect employee morale by the things I purchase.'" Within months, Simon had distinguished himself and was promoted to our Planning and Analysis group. Years later, when Facebook recruiters called for a reference, I told them, "He'll be a CEO someday, and I'll be lining up to be on his board." To create impact consistently, apply these seven key strategies. First, put passion into your work, even when tasks aren't inherently exciting. Excellence comes from mastering all aspects of your role, including the unglamorous parts. Second, prioritize progress over perfection. Overthinking and excessive planning often prevent action—instead, move forward with good-enough plans and learn through execution. As statistician George E.P. Box noted, progress comes from "motivated iteration between theory and practice." Third, become an "author" by generating original ideas to advance projects. Great contributors don't just execute assigned tasks—they propose new approaches that accelerate progress. Fourth, be a truth-teller or truth-seeker, speaking candidly about challenges while creating safe spaces for others to share perspectives. Orit Ziv, an exceptional HR executive, exemplifies this: "I tell them that we can argue and disagree and have tough conversations behind closed doors, and once we leave the room, I will always represent the decision that they made." Fifth, step into the white space by taking ownership of gaps that nobody else is filling. Sin-Mei Tsai, CTO at Joyus, explained this beautifully: "Imagine your own role and draw a circle around it. This is what you own directly. Now let's imagine each of us lining up our circles next to one another's, and you'll see that there are gaps between the circles. True owners don't just own what's in the circle. They also own everything that falls in the gaps." Sixth, go high and low by addressing both strategic issues and tactical details. Daniel Alegre exemplified this at Google, handling everything from CEO-level strategy to contract specifics when building the company's international operations. Finally, go deep and diverse by developing specialized expertise while also broadening your skills over time. Research shows that adding new job functions provides the same career boost as three years of work experience. These impact-creating behaviors build what I call "career capital"—a combination of achievements, skills, and reputation that compounds over time, regardless of whether your bigger career bets succeed or fail. Even when you miss an overarching goal, the smaller successes and capabilities you develop along the way become building blocks for future opportunities. This iterative process of choosing possibilities, taking action, learning, and choosing again drives sustainable career growth far more effectively than occasional big leaps.

Chapter 6: Learn from Failure to Accelerate Forward

Failure, despite its painful sting, can become a powerful catalyst for future success when approached with the right mindset. My experience with Polyvore illustrates how even significant career setbacks can yield unexpected rewards and growth opportunities if we're willing to learn from them. After leaving Google in 2010, I joined fashion technology startup Polyvore as CEO—my first time in the top role. The company, a precursor to Pinterest, allowed users to create shoppable fashion and décor idea boards. I thoroughly researched this opportunity, meeting with the founder Pasha Sadri multiple times and connecting with investors like Peter Fenton. Despite this diligence, I encountered unexpected challenges. Within six months, tension mounted between Pasha and me over different visions for the company. Despite my efforts to build a strong team and double the workforce to twenty people, the board ultimately chose to return Pasha to the CEO role. I felt humiliated, betrayed, and deeply shaken. It was the biggest reputational failure I'd ever experienced, and I questioned whether I had what it took to be a CEO. Yet surprisingly, this apparent disaster had several silver linings. My reputation remained largely intact due to my previous track record. Financially, I had negotiated protections that gave me significant equity in Polyvore, which later sold to Yahoo for over $200 million. Most importantly, this experience confirmed my desire to lead companies and work in e-commerce, laying groundwork for future opportunities as an investor, board member, and eventually, founder of my own e-commerce venture. When navigating failure, it's essential to diagnose the specific "impact fails" that prevent progress. The first common pitfall is spreading yourself too thin—attempting too many goals simultaneously without making meaningful headway on any of them. This "peanut butter" problem (named after a famous Yahoo memo) dilutes your effectiveness. The second mistake is mistaking motion for impact—staying busy with activities that don't yield tangible results. When reviewing resumes, I often notice candidates describing responsibilities ("worked on" or "was responsible for") rather than concrete achievements and outcomes. The third error is trying to keep your "fingernails clean" by avoiding messy situations. Bill Campbell, the legendary Silicon Valley coach, once told me to be proud of having the team at Google with "dirt under our fingernails"—tackling tough problems was challenging but vitally important work. Fourth, failing to take feedback prevents growth and adjustment. Without openness to others' perspectives, we can't identify our blind spots or improve our approach. Beyond these self-imposed limitations, external factors like bias, discrimination, and harassment can fundamentally undermine someone's ability to succeed. Ade Olonoh, a successful entrepreneur, courageously shared his experiences as a Black man: "I don't tell you about all the ways I live my life differently than you do. How I think about it nearly every day, and it's suffocating." These systemic barriers require both individual courage and collective action to address. Knowing when to persist through failure versus when to pivot to something new requires honest assessment. If you're achieving outcomes and learning but lack satisfaction over extended periods, it may be time for a change. When transitioning, maintain maximum impact by staying fully engaged until your actual departure, avoiding the mistake of "leaving before you leave." Be mindful not to linger too long without purpose, and try to create opportunities for team members who remain. Consider taking a "middle step" between big career moves—a period of reflection that allows you to process lessons learned and explore options without pressure. Adam Zbar did this after his mobile app Lasso struggled, taking time to thoroughly analyze what worked and what didn't in his previous ventures before founding Sun Basket, which grew to $300 million in annual revenue. By transforming failure into insight, you can approach your next chapter with greater clarity and conviction, turning setbacks into stepping stones toward future success.

Chapter 7: Share Your Power to Multiply Possibilities

Power isn't a finite resource to be hoarded but a renewable energy that grows when shared with others. This principle of "powerflow" represents the highest form of career advancement—using your influence to create possibilities not just for yourself but for those around you. My journey at StubHub demonstrates how power and possibility evolve through both intentional choices and unexpected challenges. After joining as president in 2017, I restructured parts of the business while investing in new products and services. I advocated for acquiring other ticketing companies to compete more effectively against rivals like Ticketmaster. However, in 2019, activists took a stake in our parent company eBay and pushed for StubHub's sale. Rather than being the acquirer, we became the acquired when Viagogo purchased StubHub for over $4 billion. This unexpected turn was professionally successful but personally disappointing, as Viagogo's CEO (StubHub's original founder) would naturally want to run the combined company. Just as I prepared to depart, COVID-19 devastated the live events industry. Overnight, StubHub went from handling billions in ticket sales to almost nothing. Instead of a smooth exit, I had to quickly restructure operations, create new customer policies, and make the painful decision to reduce our workforce by two-thirds. By June 2020, we had stabilized the company, allowing me to finally move on to my next chapter. This experience exemplifies the cyclical nature of career growth. Rather than proceeding in a straight line, careers resemble sine waves—moving through periods of ascent, plateau, and sometimes descent before rising again. Each cycle builds upon the previous one, with failures and successes both contributing to long-term advancement. Looking at my own career trajectory—from struggling graduate to Merrill Lynch, from Sky to OpenTV to Junglee to Amazon, from Google to Polyvore to Joyus to StubHub—each chapter involved risks, learnings, and outcomes that created the foundation for what followed. The frequency of risk-taking matters more than the size of any single risk. Those who take many risks of varying sizes build more career capital than those who make rare, occasional leaps or remain inactive. Even if you experience multiple failures, the cumulative impact of consistent risk-taking generally leads to greater success over time. Your "win rate" need not be perfect—in baseball, Hall of Fame players succeed just 30-40% of the time. As we develop our own power through choosing possibility, we face an important choice: Will we use our influence solely for personal advancement, or will we help create opportunities for others? My father exemplified this generosity throughout his life. Though not wealthy or famous, he consistently used his warmth, optimism, and encouragement to help others realize their potential. At his funeral, countless people shared stories of how he had changed their lives through small but meaningful acts of possibility-sharing. John Krause's journey illustrates the transformative impact of both choosing possibility for oneself and extending it to others. After losing his father at age four and growing up with an addicted mother, John spent sixteen years cycling through addiction and incarceration. When his grandmother died during his final prison term, he faced a pivotal choice—either surrender to his circumstances or choose a different path. Upon release, he secured a job recycling cooking oil, later starting his own business that generated half a million dollars in sales within eighteen months. Not content with personal success, John founded Big House Beans, a coffee roasting business dedicated to hiring formerly incarcerated individuals. The company operates under the philosophy of "birthing potential through highlighting diversity" and giving second chances to those society often overlooks. As John's experience shows, even someone starting with seemingly nothing can unleash tremendous inner power through consistent choosing, and then extend that power to others. The most profound lesson from successful risk-takers is that possibility and power aren't zero-sum games. They're abundant resources that multiply when shared. By consistently choosing possibility for yourself while helping others access their own opportunities, you create ripples of impact far beyond what you could achieve alone. This is the ultimate reward of mastering risk—not just personal achievement, but the ability to transform lives around you.

Summary

Throughout this journey, we've seen that risk-taking isn't about making a single heroic leap but rather a continuous process of choosing possibility through multiple decisions over time. The most successful people don't avoid failure—they learn to move through it, gathering wisdom and building resilience with each experience. As Gary Zukav wisely notes, power comes when you see yourself not "as a victim who reacts to your circumstances," but "as a creator who chooses your response" to them. This perspective transforms how we approach both opportunities and challenges. Your next step is beautifully simple: make one choice today that moves you toward possibility, however small it might seem. Apply for that role that feels slightly out of reach, share your idea in the next meeting, or reach out to someone whose work you admire. Then tomorrow, make another choice. With each decision, you'll not only build your own career capital but develop the confidence to take increasingly meaningful risks. Remember that the journey to any worthwhile destination unfolds through many choices, both large and small, and the power to shape your future lies in your willingness to keep choosing, learning, and moving forward—even when the path ahead isn't perfectly clear.

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Sukhinder Singh Cassidy

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