Chapter 1
The Risk-Taker's Advantage: Breaking Free from Paralysis
In the world of career development and personal growth, few books have garnered as much attention as Sukhinder Singh Cassidy's "Choose Possibility." As a former Google executive who's launched three companies and served on boards of major corporations, Singh Cassidy offers a refreshingly practical approach to risk-taking that has resonated with professionals across industries. The book has been praised by tech leaders like Reid Hoffman and Sheryl Sandberg, with The Wall Street Journal calling it "essential reading for anyone looking to make a career leap." What makes this work particularly compelling is how it dismantles our conventional understanding of risk-transforming it from a terrifying cliff-jump into an accessible, iterative process anyone can master. In a culture that often glorifies the "all or nothing" entrepreneur while leaving everyone else paralyzed by fear, Singh Cassidy's framework provides a middle path that's both ambitious and attainable.
Chapter 2
Ditch the Hero's Journey: Risk Is a Process, Not an Event
We've been sold a dangerous myth about risk-taking-that it's a single, monumental leap that will make or break us. This "Myth of the Single Choice" creates immense pressure to make the perfect decision and prevents many of us from taking any action at all.
The reality is far different. Success rarely hinges on one dramatic choice but emerges from a series of decisions both large and small. Consider Anjali Sud, Vimeo's CEO, whose path included investment banking, retail, and marketing before she found her leadership role. Her journey wasn't a straight shot to glory but a winding path of diverse experiences that collectively prepared her for success.
This misconception about risk creates supporting myths that further paralyze us: we must prepare zealously with a perfect plan; if we're passionate and hardworking enough, we can control outcomes; and when we fail, it's entirely our fault. These beliefs create a cycle of anxiety where we perpetually postpone action.
The most dangerous career choice might be what seems safest: not moving at all. When you remain static, you fail to develop new skills as quickly as your peers, making it increasingly difficult to compete in the future. Even when a risk doesn't pan out, you typically learn more than by staying in a comfortable situation that no longer challenges you.
Nicky's story illustrates how letting go of the Myth of the Single Choice can transform a career. After years of struggling with her declining optometry practice in a failing mall, she finally took action-first negotiating a flexible lease, then pausing her practice entirely to explore new options. Only by taking the risk to shut down her mall practice did Nicky open pathways for new possibilities, eventually finding a better opportunity with a venture-backed medical company that provided improved financial terms, a location closer to home, and continued service to her patients.
Success didn't happen overnight but emerged from a series of smaller and then bigger choices over several years. By releasing her fear of the Single Choice, she gained the courage, flexibility, and momentum needed to start her next journey.
Chapter 3
Pump Your Risk-Taking Muscles: Small Steps Build Big Confidence
Learning to take risks is like building a muscle-it strengthens with regular exercise. Singh Cassidy's education began in summer 1989 when she took a job selling vacuum cleaners. There, she witnessed salespeople putting their egos on the line daily, handling constant rejection while maintaining a surprisingly fun atmosphere. This experience taught her the value of taking small risks daily, a lesson she carried throughout her career.
We typically think of risk as dangerous, but risk-taking is more balanced-it's simply taking action involving uncertainty to achieve a goal. Instead of waiting for life-altering decisions to take our first risk, we can start small right now. The author learned this normalized view of risk from her father who, despite appearing conventional as a doctor, was an entrepreneur who took continuous small risks in his medical practice.
Taking small risks regularly makes risk-taking progressively easier. You don't need to be a natural risk-taker to become competent at experimenting in daily life. As you practice, your tolerance for rejection increases and your worries about personal insult diminish. Each subsequent attempt becomes smarter, informed by previous results.
Sometimes a single large failure can jump-start risk-taking muscles. "Gina," a successful software company CEO, dropped out of high school with Fs and Incompletes. After hitting rock bottom, she eventually attended boarding school in Europe, finished high school, earned a computer science degree, and founded a successful tech company. This early failure didn't set her up for success by teaching technical skills, but by demystifying failure and increasing her tolerance for risk.
Most high-profile risk-takers didn't start with their biggest risk-it was likely their fiftieth or five-hundredth. Whether reaching out to new contacts, speaking up in meetings, or trying small investments, the key is to keep taking risks. Risk-taking not only becomes easier with practice-it becomes fun, giving you "something about feeling alive and getting a rush."
Chapter 4
The Power of Pipelining in Parallel: Multiple Paths to Success
When facing career uncertainty, pursuing multiple opportunities simultaneously can yield unexpected success. After graduating university without a clear path, Singh Cassidy reluctantly accepted a position at TD Bank while simultaneously pursuing an opportunity at Merrill Lynch through a friend's connection. During this period, she also applied to medical school, the Foreign Service, and briefly considered law school-creating multiple pipelines in parallel. This approach ultimately landed her a dream job at Merrill Lynch while strengthening her conviction in her choice through exploration of alternatives.
The strategy of pursuing multiple risks simultaneously mirrors how financial professionals create diverse investment portfolios or how students apply to various colleges. By exploring multiple paths at once, we maximize opportunities while lowering overall risk on any single bet.
Despite this logic, we often constrain our professional choices too early, fearing that too many options will overwhelm us. While focus is important after choosing a path, exploring all potential opportunities before committing typically yields better results. This approach helps identify goals, uncovers multiple pathways to success, mitigates risk through diversification, and opens the door to serendipitous opportunities.
Entrepreneurs frequently use parallel pipelining to drive results. Ashvin Kumar, founder of Tophatter, exemplifies this approach. Rather than developing a single app, he and his partner built numerous products to discover what would succeed. Over eighteen months, they created and tested 15-20 e-commerce products. Though many experiments failed, the process helped them refine their skills and interests. After multiple iterations, they launched Tophatter, which immediately showed promise unlike their previous ventures.
Processing opportunities sequentially rather than in parallel increases the risk of never making a choice, as you can easily reject each option while waiting for the "perfect choice." Pipelining in parallel creates momentum and conviction through rapidly accumulated knowledge.
To master pipelining, create your own discovery timeline rather than reacting to others' schedules; distinguish between escaping negative situations and pursuing positive opportunities; find a dedicated brainstorming buddy who generates possibilities optimistically; and embrace passive pipelining by staying open to connections even when not actively job-searching.
Chapter 5
Why Proximity Beats Planning: Getting Close to Your Goals
We often believe we need a perfect, detailed plan before taking action toward our goals. This myth of perfect planning keeps us stuck in preparation mode rather than execution. A plan is merely a theory about how our future might unfold, and we mistakenly think more precise plans guarantee success.
When our ambitions are still forming, we feel we lack permission to act until we've done the "hard work" of planning. This leads to excessive plotting that feels productive but actually prevents progress. Even after taking action, over-planning can lock us into rigid paths that blind us to unexpected opportunities.
Our obsession with planning often stems not from logic but from emotional discomfort with uncertainty. As Oliver Burkeman notes, we invest in detailed future visions not necessarily because they'll help us achieve goals, but because they alleviate our present anxiety about the unknown.
While planning alone doesn't shrink the distance between ourselves and our ambitions, proximity to opportunity does. Inserting ourselves into environments filled with people who routinely do what we aspire to benefits us in three crucial ways.
First, proximity helps us visualize our goals by seeing them in action. Rather than just reading about entrepreneurship, taking a side hustle or working at a startup provides tangible experience of what the goal actually feels like.
Second, proximity enables learning through apprenticeship. By helping someone execute their plan, we learn by watching, copying, and doing. Social learning theory and neuroscience confirm that we learn efficiently by observing successful behaviors.
Third, proximity increases our access to opportunities through networks. Professor Sydney Finkelstein describes how successful practitioners create "networks of success" that open doors for their proteges.
Alyssa Nakken, Major League Baseball's first full-time female coach, didn't achieve her historic position through meticulous planning. After playing Division I softball in college, she initially took a safe job as a financial planner. Hearing clients' stories about career adventures inspired her to seek more passion in her work.
Without a clear goal, Nakken took a directional leap by quitting her job, moving to San Francisco, and enrolling in a sports management program. Through internships with various sports organizations, she tested different paths while continually refining her interests. This exploratory approach eventually led to her groundbreaking appointment as assistant coach for the San Francisco Giants.
Nakken's story demonstrates how moving directionally toward general interests and iterating forward can be more effective than waiting for perfect clarity. As one CEO describes it, career progress is like traversing monkey bars-you don't need to see all the rungs, just reach for the one in front while letting go of the one behind.
Chapter 6
FOMO > FOF = Action: Managing the Fear Equation
When confronting risk, our actions are determined by a simple equation: if our fear of missing out (FOMO) exceeds our fear of failure (FOF), we'll act. Risk-taking isn't about fearlessness but about negotiating the relationship between these competing anxieties.
To manage the fear equation, first imagine the "choice-after-the-choice"-what you would do to recover from potential failure. Jeff Bezos distinguishes between Type 1 decisions (irreversible "one-way doors") and Type 2 decisions (reversible choices). Most decisions are Type 2, but even with Type 1 decisions, we typically have options for moving forward after failure.
Second, name all your risks and fears. We face three types of risks in career choices: financial, reputational/ego, and personal. Ego risk-the threat to our self-worth and identity-is often the most emotionally powerful yet potentially easiest to overcome since it resides in our psyche. Untangling and naming these fears makes them more manageable.
Third, size your risks. Risk magnitude isn't absolute but relative to your present circumstances. Risks are smaller when they offer mostly upside with few downsides, or when viable choices-after-the-choice exist. They become larger when they represent one-way doors with few recovery options.
Fourth, plan for the downside more than the upside. Expert negotiators focus on mitigating the risk of future failure before finalizing deals. For small to medium risks, mentally identifying choices-after-the-choice may be sufficient. For larger risks, detailed contingency planning is essential.
Nothing reduces future fear of failure like surviving actual failure. Ade Olonoh's experience with Formspring demonstrates this-despite the devastating failure of his once-promising social platform, he emerged with fundamentally changed attitudes toward risk, recognizing that the time horizon is truly long and individual failures won't wreck an entire career.
While fear never disappears entirely, you can choose possibility by addressing both sides of the fear equation: embracing galvanizing fears like FOMO while managing negative emotions like FOF. Becoming a "realistic optimist" means remaining realistic short-term while maintaining optimism long-term, recognizing that you can keep choosing your way through failures.
Chapter 7
Put Who Before What When Taking a Risk: The People Factor
We often obsess over finding work aligned with our passions, assuming we'll be more motivated by subject matter we love. But since we rarely work alone, the "who" factor significantly influences our success more than the "what." Great colleagues can increase our engagement and make even initially uninteresting work become fascinating through our interactions with inspiring, motivated people.
Working with exceptional people accelerates our learning through four distinct mechanisms: osmosis (observing and emulating skilled individuals), active challenges (being pushed beyond our comfort zones with support), coaching (receiving consistent feedback and skill development), and social learning (benefiting from diverse, skilled teams). Even if a venture ultimately fails, working alongside great people helps us build capabilities more quickly and expand our thinking.
Rather than cold networking at events, our deepest professional connections form our most valuable network. People who've worked closely with us are more willing to vouch for our abilities and open doors to new opportunities. Singh Cassidy describes her network as three rings: the outermost comprising cold contacts, the middle consisting of acquaintances and former colleagues, and the innermost "best network" of people she's worked with deeply and meaningfully-those for whom she'll put her credibility on the line.
Exceptional leaders who supercharge careers come in unexpected packages. Sydney Finkelstein's research shows "superbosses" have diverse personalities and backgrounds but share an ability to innovate while developing talent. Three key signs mark leaders worth following: they attract and retain diverse, smart talent; they possess complementary skills to your own; and they share your core values.
When weighing career risks, we don't always need to choose between interesting work and great people. Finding both creates the optimal environment for growth and fulfillment. By prioritizing people who can teach, complement, challenge and motivate us, we'll likely find ourselves more engaged in whatever work we're doing.
Chapter 8
It's Not All About You: Recognizing External Forces
Despite Singh Cassidy's impressive career trajectory from junior business development manager to high-ranking Google executive, she acknowledges that external factors played an enormous role in her success. Arriving in the Bay Area in 1997 just as the internet was exploding, she "rode one of the largest business tailwinds imaginable."
Many people neglect environmental factors when making choices, focusing instead on personal effort and perfect planning. Society's emphasis on self-determination leads us to internalize both success and failure as entirely our own doing. While humans have a biological need to feel in control, clinging to this myth actually gives us less control over our destinies.
Smart risk-takers recognize that external forces significantly influence outcomes, seeking to identify and ride tailwind trends while avoiding headwinds. This requires looking beyond personal control to evaluate how changing circumstances should inform our choices.
Companies that identify and exploit external trends grow much faster than those focused only on internal improvements. When we join organizations riding tailwinds, we experience disproportionate career growth as roles expand and advancement opportunities multiply. Satya Nadella exemplifies how riding tailwinds can propel careers-by recognizing cloud computing as a massive trend and championing Microsoft's Azure platform despite internal resistance, he positioned himself to become CEO and lead one of corporate history's biggest turnarounds.
While divisions facing headwinds experience pressure to accelerate performance, individuals aren't powerless. First, recognize the magnitude of negative forces affecting career growth. Rather than fostering victimhood, honestly evaluating external environments gives us more autonomy. We might discover stagnant company growth will limit advancement or resource constraints will hamper our goals.
While leaving is one option, challenging circumstances often provide excellent career opportunities by forcing us to develop flexibility and resilience. Jane Fraser's rise to become Citigroup's first female CEO came through successfully managing troubled divisions-"Fraser made a name for herself overhauling Citigroup's trouble spots."
When evaluating past risk-taking attempts, examine not just your efforts but the macro conditions under which you operated. Forces are always at play that we might overestimate, underestimate, or fail to predict. We're never as terrible as we perceive in our worst outcomes, nor as brilliant as others think when we succeed.
Chapter 9
Well, Some of It Is: How to Bet on Yourself
While external environments matter greatly in risk-taking, who we are and how we're wired play equally critical roles. To maximize our chances of success, we must identify not just our passions but our values and strengths. Too often we follow others' advice without considering our unique gifts, choosing paths that seem safe but align poorly with who we are.
Self-awareness forms a three-layered "sandwich" that guides our choices. At the top are our passions-pursuits that naturally captivate us, though these can evolve over time. The middle layer contains our "trademark" strengths-innate qualities that distinguish us, plus acquired skills and knowledge. The bottom layer holds our values-stable life goals that guide our perception and behavior.
Most of us lack clarity about our passions, strengths, and values. In leadership talks, when Singh Cassidy asks who can name their trademark strengths, only about a quarter respond. This self-knowledge gap is dangerous-we risk making choices incompatible with who we are. Tasha Eurich found that while 95% of people think they're self-aware, only 10-15% actually are.
Our weaknesses-our "kryptonite"-are often shadow sides of our trademark strengths. Though confronting them feels uncomfortable, doing so helps us make better choices and lower risks of self-sabotage. Acknowledging imperfections actually helps us take risks more boldly by reducing ego threat-we feel less pressure to appear perfect and obsess less about looking foolish.
Nick Grudin's career illustrates how we discover ourselves through our choices. At Facebook, he values how "every year it feels like something really new is happening" that forces him to grow. Smart risk-taking means betting on our natural strengths and values while recognizing that new choices reveal previously hidden talents. With each choice, we learn more about ourselves, making future bets more rewarding.
Chapter 10
The Myth of Risk and Reward: Nonlinear Outcomes
Despite careful planning and due diligence, Singh Cassidy's CEO role at Polyvore ended in failure after just six months. Despite her efforts to build rapport with founder Pasha Sadri and establish productive board relationships, tensions mounted as their leadership styles clashed. The board ultimately chose Pasha to return as CEO, leaving Singh Cassidy humiliated and questioning her abilities.
Yet surprisingly, this failure yielded unexpected rewards. Her career remained intact, and financial protections she'd negotiated meant she retained significant equity in Polyvore, which later sold to Yahoo for over $200 million. More importantly, the experience confirmed her love for the CEO role and e-commerce industry, leading to future success as an investor, board member, founder, and CEO again.
Our cultural conditioning leads us to expect a linear relationship between risk and reward-the bigger the chance, the bigger the payoff. This perspective stems from how we experience growth in childhood education, corporate career ladders, and even video games, where progress follows clear, sequential paths.
In reality, the connection between risk and reward is rarely so neat. We take risks for multiple reasons, pursuing several goals simultaneously with results unfolding over months or years. Our outcomes resemble scatter charts rather than straight lines-sometimes small risks yield outsized rewards, while major risks produce modest returns.
Taking many risks consistently, even after failures, makes us more likely to achieve outsized rewards over time than making occasional big leaps. Regular risk-taking improves our ability to forecast, assess probabilities, and understand our instincts, enhancing our decision-making.
Corey Thomas, CEO of Rapid7, exemplifies this path-he left Microsoft for a 30% pay cut at startup Parallels, then took another 20% cut to join Rapid7 as CMO. When Rapid7's CEO unexpectedly departed before their IPO, Thomas stepped into the role despite lacking experience. He successfully led controversial strategic changes and took the company public in 2015, growing it to $350 million in annual revenue. His success came through a series of calculated risks that built relationships and experience, positioning him to benefit from unexpected opportunities.
Chapter 11
The Sines of Growth: Embracing Career Cycles
Career growth doesn't follow a straight line from A to B. Each chapter follows its own circuitous path as we anticipate opportunities, make choices, drive results, learn, deal with expected and unexpected forces, and make new choices. Career growth resembles a sine wave-taking risks, creating successive impacts, responding to conditions, reaching conclusions, and taking risks again.
Successful careers follow sine wave patterns of ups and downs that most people don't see. Take Stacy Brown-Philpot, who rose from modest beginnings in Detroit to become TaskRabbit's CEO. Her path included calculated risks: attending Wharton despite financial constraints, joining pre-famous Google in a lower position than her peers, moving to India while maintaining a long-distance marriage, and leaving Google for TaskRabbit when it wasn't considered a hot startup. Like other successful leaders, her career appears as a series of peaks to outsiders, but actually includes valleys that ultimately contributed to her growth.
To avoid career stagnation, we must practice risk-taking regularly. The frequency and variety of risks matter tremendously. Those who take many risks of varying sizes can sustain multiple failures yet still advance significantly. Even taking numerous small risks propels career growth. The danger zones are taking too few risks (stagnation) or betting everything on one or two massive gambles (requiring extraordinary luck).
Beyond frequency, your win rate affects career trajectory. The goal is for your total career wins (considering both quantity and magnitude) to exceed your losses. Win rates vary by profession-car salespeople might celebrate 20% while surgeons need 90%-but consistently delivering positive impact matters more than succeeding in every individual move.
The greatest career obstacle isn't failure but inaction. Taking smart risks, breaking goals into manageable pieces, driving results, responding adaptively, and continuing to move forward allows us to realize possibilities we seek and discover new ones. As we build impact, agility, resilience and confidence-even through failures-we accumulate rewards, though rarely exactly as imagined.
Chapter 12
Possibility and Powerflow: Abundance Thinking
When asked what advice she'd give her younger self, Singh Cassidy emphasizes that possibility and power aren't zero-sum games-there's enough for everyone. Early in our careers, we often view success as competition for scarce opportunities. Our culture reinforces this by elevating celebrities and business leaders as distant, powerful figures.
True power comes not from achievement alone but from our ability to keep taking risks, creating impact, and adapting. As Gary Zukav suggests, power emerges when we see ourselves not as victims reacting to circumstances but as creators choosing our responses.
Singh Cassidy's hero isn't a billionaire entrepreneur but her father-the most powerful person she's known who embodied choosing possibility. Quiet yet charismatic, he cared more about learning than others' opinions. His greatest gift was helping others realize their possibilities, generously giving time and encouragement. Like renewable energy, personal power regenerates as we choose possibility, and the more we generate, the more we can distribute to others-creating "powerflow" rather than just power.
If power is abundant within each of us, why do so many struggle with inequality and lack of opportunity? While choosing possibility is our first step toward impact, larger forces and systemic biases create unequal distribution of possibility. At Joyus, Singh Cassidy became increasingly aware of gender inequities in tech. Her survey of nearly 100 women tech leaders revealed that while 84% would recommend entrepreneurship to their daughters, 86% witnessed unconscious bias in tech, with women often labeled "aggressive" or expected to be "likable."
After her op-ed received overwhelmingly positive response, she launched theBoardlist, a talent marketplace connecting diverse leaders with board opportunities. By 2020, theBoardlist grew to 16,000 members, facilitated nearly 2,000 board searches, expanded to include leaders of color, and raised venture capital.
John Krause's story exemplifies choosing possibility from the most difficult circumstances. 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 in 2009, he faced a pivotal choice between surrendering to drugs or building a new life. He chose possibility, eventually launching Big House Beans, a coffee company that intentionally hires formerly incarcerated people. His "Coffee with Purpose" business grew to $1 million in sales by 2019, demonstrating how choosing possibility unleashes inner power that naturally extends to helping others.
