Choose Possibility - Book Summary

Embark on a journey to grasp risk and unleash potential

There's a fundamental fallacy that plagues humankind — the perception of risk.

Too frequently, we are consumed with thoughts of the pivotal decisions which we believe can shape our existence. Within the gravity of these significant life choices, we view risk as something daunting and dark, filled with unimaginable fear. We tremble at the thought of one wrong turn that could lead to our financial ruin or tarnish our social standing.

However, the reality is that these monumental crossroads are few and far between. If you inspect the intricate fabric of life, you'll find that it's woven from countless minor risks — instances that present us with a spectrum of possibilities. It could be the decision to voice your opinion in a meeting or to respond to that pending call from a headhunter.

Risk, thus, is not a static concept but a dynamic state of unpredictability filled with potential. Through this narration, we aim to equip you with the wisdom and audacity to accept risk wholeheartedly, showcasing that it's the vehicle to drive towards endless possibilities and craft your own destiny.

In the course of this narrative, you will discover

how to tackle the unpredictable ebbs and flows of your professional journey;

how to constructively juxtapose your apprehension of failure with the regret of missed opportunities; and

a novel, more productive perspective on the concept of power.

Break free from the hero's myth and explore the potential of parallel paths

Picture this — it's the spring of 1993 and Singh Cassidy is gearing up to launch into the professional realm. With her graduation just around the corner, she was buzzing with anticipation and eagerness to set foot into the world of investment banking or perhaps management consulting.

Dressing up her dreams in power suits and giant paychecks, she hoped for a golden ticket into the world of C-suite execs and fortune 500 companies. However, as spring gave way to fall, the harsh reality dawned on her. Despite numerous applications to leading firms, the job offers she yearned for were nowhere in sight.

Confined to her childhood home in Ontario, Canada, she was confronted with the sight of her classmates embarking on their respective professional journeys. Just a fresh graduate, yet she was gripped by the fear of early failure.

The key insight to imbibe here is: Liberate yourself from the myth of a hero's journey and consider treading multiple paths simultaneously.

We live in a society that idolizes heroic narratives — tales of individuals who stake everything to defeat adversities, prove their mettle, and accomplish their aspirations. In the process of reminiscing about these narratives, we often simplify the hero's journey into a linear progression, overlooking the multitude of potential paths that branched out along their journey.

Similar distortions can color our career perceptions. When you convince yourself that a single decision will etch your identity, you turn a blind eye to the myriad alternative paths that lay before you. You catastrophize your minor hiccups, enabling your fear of failure to dominate your actions. This could potentially drive you to give up.

However, if you opt for a more balanced approach and take several minor risks, you'll soon realize that it helps build momentum and spur unexpected opportunities.

Take the instance of Ashvin Kumar, an entrepreneur who launched an e-commerce startup in 2008. Rather than dedicating all resources to a singular platform, his company launched nearly 20 apps within a year and a half. While each app demanded minimal capital investment, the cumulative volume provided ample room for feedback. Essentially, it was a numbers game. This approach of expanding his options not only mitigated his risk but also amplified his prospects for success. Eventually, one of his apps, Tophatter, a live auction platform, soared in popularity, amassing millions of users.

Back in 1993, Singh Cassidy employed a similar multi-pronged strategy to break free from her post-college ennui. She accepted an entry-level position at a local bank while simultaneously exploring various low-risk opportunities — applying to medical school, taking Canada's foreign service examination, and attempting the Law School Admissions Test.

The game-changer came in the form of a train ticket to New York City. In the next part of our narrative, we'll explore how this minor decision catapulted her into the dynamic world of Wall Street, unlocking a world of untapped possibilities.

The winds of luck blow strongest for those who present themselves

One quiet evening at her parent's house, Singh Cassidy experienced a turning point in her career journey. Among the pile of rejection letters, one stood out from the rest. It was from the banking behemoth Merrill Lynch, and though it carried the familiar message of rejection, it ended with an unexpected invitation to visit their office in New York City.

While Singh Cassidy perceived this invitation as mere courtesy, a simple band-aid to heal the sting of rejection, her father saw it through a different lens.

Having moved from Africa to Canada at a young age and established his own medical practice in a small town, he had faced his fair share of overlooked opportunities. He immediately recognized the potential this invitation held and promptly bought a train ticket to New York for his daughter.

The crucial insight here is: Fortune smiles upon those who make themselves available.

Purchasing that train ticket turned out to be a serendipitous decision for Singh Cassidy. A casual tour of Merrill Lynch transformed into an impromptu interview and eventually led to an invitation for a full-day tryout for the position of an analyst. A month later, her performance won her the job.

This transition from a small town in Ontario to the buzzing streets of Wall Street taught her an invaluable lesson — the proximity to your dreams can offer hidden opportunities that could bring you closer to achieving them. But this was only the beginning of her realization about the interconnection of proximity and opportunity.

After a year in New York, Singh Cassidy secured a position at Merrill Lynch in London, England. Here, she joined British Sky Broadcasting in an apprenticeship under Sky's founders. All this while, she was continuously expanding her professional network. And it was through this network that she got wind of a historic event brewing in California. In 1996, Singh Cassidy purchased a ticket to San Francisco, reaching the city just as the tech boom was taking off.

With each risk she embraced, a fresh opportunity unfolded, which further opened up new prospects. This unpredictable journey was something she could not have mapped out. But as a LinkedIn study on the careers of thousands of individuals suggests, high-level consultants and CEOs often rise faster when their journeys are winding rather than straight.

This is not to say that you should toss your career plans out the window and abandon caution. As we shall see next, embracing risk also involves confronting and understanding your fears.

Conquering your fear of loss is the key to seizing momentum and taking the plunge.

Singh Cassidy's sister, Nicky, found herself in a dire situation. Her once flourishing optometry business was now on the brink, with late-night work sessions becoming her new normal.

Her practice was tucked in a shopping mall with dwindling footfall, competition was heating up in the local market, and online retailers were starting to undercut her prices.

Nicky knew she had to make a move, but the thought of losing what she had built — the invested money in equipment, her patient community, and her loyal team — filled her with dread.

The key lesson here is: Overcoming your fear of loss can set you in motion, enabling you to take necessary risks.

Fear of loss is a potent inhibitor, but in the dance of risk and opportunity, it often partners with another fear: the fear of missing out, or FOMO. As long as our fear of loss overshadows our FOMO, we stay stagnant. But by dissecting our fears, we can shift this balance and summon the courage to act.

The initial step is to acknowledge and define your fears. Are they financial? If so, can you quantify the potential loss? If it's a fear of professional or personal failure, separate legitimate apprehensions from ones derived from ego protection. Next, project your fears into the future; would they still carry the same weight three months, three years, or a decade down the line? If your fears do come true, what's next? Ask yourself whether the damage is entirely irreparable. Usually, major decisions can be reversed. Lastly, devise a contingency plan to safeguard against permanent harm.

Let's take the case of Alan Eustace, a 58-year-old Google engineer who made a jump from the stratosphere back to Earth in 2014. Eustace, an otherwise unremarkable computer scientist, conducted over 250 tests on his jumpsuit for three years leading up to his monumental leap. He prepared for every conceivable glitch until his FOMO tipped the scale over his fear. Armed with the confidence of having confronted and conquered his fears, he made the successful 25-mile jump from the sky to the Earth.

Like Eustace, Nicky too faced her fear of loss and emerged victorious. She took a methodical approach to examine her concerns, adopted her sister's advice, and pursued multiple low-risk options to create new opportunities. When a job with promise presented itself, she was prepared and willing to take the leap. Although she had to let go of her optometry practice, she regained control of her life and opened a fresh chapter in her career.

When deciding on a career transition, prioritize the people you'll be working with.

When Singh Cassidy left the corporate halls of Merrill Lynch to join the entrepreneurial journey led by Sam Chisholm and David Chance, founders of British Sky Broadcasting, she found herself in the company of individuals who were not just visionaries but were passionately working to turn that vision into reality.

This ignited a desire in her to be a part of an organization at its infancy stage, where innovation and excitement could be the everyday order. So, in 1997, she took up a managerial role at OpenTV, an interactive television start-up based in California.

However, her enthusiasm was met with a dampener on her second day. Her boss advised her to lower her intensity, which according to him, didn't align with the office culture. This marked the beginning of a downward spiral at OpenTV.

Here's the takeaway: When contemplating a career shift, always prioritize the people aspect.

Chasing a career in a field that you find fascinating is certainly appealing, but remember, unless you are going to work solo, the colleagues you surround yourself with will have a substantial impact on your success or lack thereof.

Even the perfect job can turn into a nightmare if you're stuck in a toxic work environment. Conversely, motivating coworkers can make even a monotonous role seem exciting and challenging.

In considering her transition to OpenTV, Singh Cassidy overlooked one critical aspect: the people she'd be working with. The zeal and commitment that were her assets at Merrill Lynch and Sky were perceived as a cultural mismatch at OpenTV.

Not one to be disheartened, Singh Cassidy set out to explore new opportunities and came across Junglee, an information management start-up. While the industry itself seemed less than thrilling, the people at Junglee struck a chord with her — they were ambitious, intelligent, straightforward, and shared her passion.

Embracing the welcoming environment at Junglee, she immersed herself in aiding her new colleagues, and in the process, built relationships that continued to positively influence her professional journey for many years to come.

When you discover a workplace that feels like your professional tribe, seek out mentors who are keen on cultivating talent around them. Be a sponge, absorb their wisdom. Form bonds with colleagues you can turn to for unbiased, constructive feedback. Over the course of your career, you will need their sound advice. And don't forget to foster friendships with those who understand your dreams and amplify your enthusiasm. Together, you can spur each other on for the long run.

Understanding oneself and acknowledging external factors is critical.

While serving as a manager at Junglee, Singh Cassidy had an entrepreneurial itch that led her to build her own startup, Yodlee, a venture that attracted Amazon's attention and resulted in a handsome buyout. Subsequently, she established another tech enterprise, which also fetched a lucrative deal. Next, she joined Google, where she was instrumental in launching Google Maps and swiftly rose to the ranks of the tech giant's upper echelon.

Even with her relentless determination driving her skyrocketing career trajectory, Singh Cassidy acknowledges the significant role played by a favorable external factor: the tech boom of the late '90s and early 2000s.

The critical takeaway here is: Recognize the importance of self-understanding and acceptance of elements outside your control.

When it comes to attributing success, it's easy to credit individual effort, skills, and intelligence. However, achieving success is not solely about what you bring to the table. The contributions of others and the power of historical trends play an equally significant role in propelling you to the summit.

Conversely, failure doesn't squarely fall on your shoulders either. Believing that you can control all the outcomes can lead to self-blame and the erroneous notion of personal inadequacy when confronted with failures. Not only does this mindset inflict unnecessary mental suffering, but it's also devoid of truth. Just as tailwinds can assist in a project's success, formidable adversarial forces — headwinds — can hinder a project.

Despite the challenges headwinds pose, they can also offer unparalleled opportunities for professional growth.

Consider Jane Fraser, Citigroup's inaugural female CEO. Despite facing daunting headwinds — the near-collapse of Citigroup's Latin American banking operations coupled with the subprime mortgage crisis — she successfully steered the financial institution out of turbulent waters, thereby showcasing her adaptability and tremendous resilience. If you find yourself battling headwinds, take solace from the knowledge that this hardship is honing a rare set of skills.

However, not all headwinds are worthy adversaries. For example, constantly pushing against a negative company culture, won't necessarily make you more attractive to prospective employers. To identify if you're in such a situation, you must first know yourself.

Evaluate your passions, skills, values, and see if they align with your company's ethos. Seek outside perspectives from mentors and unbiased colleagues. Recognize your shortcomings and strive for progress.

If after thorough self-examination, you conclude that the battles aren't worth it, it's time to let go, embrace change, and take the next leap. Choose the road of possibilities.

Use strategies from smaller risks to tackle bigger ones.

So far, we've explored the importance of being in proximity to our objectives, the people who join us on our journey, understanding oneself, and acknowledging the circumstances outside our control. We've come to recognize that taking risks isn't about making one life-altering decision, but it's an ongoing process.

However, some risks - like a mid-life career shift or moving to a different part of the country - are undoubtedly more significant. The stakes in these situations are high. So, how should one approach these situations?

The main point here is: You can apply strategies learned from handling smaller risks to navigate the larger ones.

You can demystify big risks by dissecting them into potential costs and opportunities — essentially, analyze both your fear of loss and your fear of missing out.

Start by listing and prioritizing each component. An opportunity can be evaluated based on its potential to fulfill your ambitions, its alignment with your personal strengths, weaknesses, and values, the prevailing headwinds and tailwinds, and lastly, the people involved. Assigning a score to each of these factors allows you to gauge the overall potential of the opportunity.

Next, delve into the potential downsides. Assess the potential financial losses, potential damage to your reputation or self-esteem, or any personal losses that could occur. Ask yourself if the decision is reversible — is it a two-way door? Do you have a contingency plan in place? By rating these elements, you can calculate a risk score to compare against your opportunity score.

However, even after methodically enumerating and weighing the pros and cons, your instinct might pull you in a certain direction. Don't brush it aside. We humans gather a wealth of information that doesn't always surface in our conscious thoughts. Your instincts could be your subconscious alerting you of something.

That said, instincts aren't always right. To counterbalance the peril of impulsively following your gut against the advantage of trusting your intuition, pay attention to your instinct, but question it. Repeatedly cross-examine your feelings with factual data to forge a solution that appeases both your gut feeling and your rational mind.

The relationship between risk and reward is not a straightforward one.

When Singh Cassidy assumed her first role as a CEO, it was not without some reservations. The position was at Polyvore, a fashion-centered e-commerce platform where she would work alongside its founder. She was being tasked with leading the company, while its creator would still have a significant presence in the organization.

She tried to foster a relationship of honesty and respect with the founder by organizing regular coffee meetups. However, inevitably, a rift developed between them due to mismatched visions for Polyvore. This disagreement escalated to a point where Singh Cassidy was relieved from her position.

She initially saw this as her greatest professional failure, but over time, she began to see the brighter side of things.

The main point here is: The correlation between risk and reward can often be non-linear and unpredictable.

Despite losing the job, Singh Cassidy didn't enter it blindly. She had negotiated a stake in the company, and under her leadership, Polyvore had grown rapidly. After her departure, the company was acquired by Yahoo, which resulted in a significant financial gain for her. Moreover, her brief but impactful tenure as the CEO caught the attention of other companies and provided her with the impetus and experience to establish her own online shopping platform, Joyus.

We often assume that taking a massive risk will yield a substantial reward. However, the results can be varied. A job loss might lead to new professional relationships, learning opportunities, or inside information about investment prospects, and these results may materialize at unexpected times. As we explore multiple possibilities, the outcomes of our decisions accumulate over time, leading to cycles of highs and lows, while the overall trajectory of our careers trends upwards.

Some risks, however, yield clear-cut results. For example, in five years, Singh Cassidy would ascertain the viability of Joyus. Waiting for this pivotal result can also be valuable, offering ample time to maximize your professional growth.

Remember to pour your passion into every aspect your new project demands, even the seemingly mundane parts. Welcome the micro-level details and the macro-level view. Understand the headwinds and tailwinds. Investigate the root cause of persistent issues, share your findings, and seek innovative solutions.

By working diligently and intelligently in all unpredictable facets the project requires, you'll not only develop a diverse set of skills, but you'll also create new opportunities as the bigger picture comes into focus.

Turning failure into a stepping stone and strategically maneuvering towards new opportunities.

Joyus, the fashion e-commerce start-up initiated by Singh Cassidy, had an exciting and turbulent journey. She rallied a top-notch team, secured multimillion-dollar investment, and patented an innovative e-commerce video player. The in-house produced videos were not just sleek and stunning but also interactive, enabling users to directly purchase the displayed products.

The flip side, however, was that these videos were quite expensive to produce. Despite doubling their revenues every year, Joyus struggled to offset the high production costs. After six tumultuous years, Joyus was sold to another company.

Unlike her experiences with OpenTV and Polyvore where the setbacks were sudden, the disillusionment with Joyus was more prolonged, spread over years full of minor victories. But this presented an even larger learning curve.

The main takeaway here is: Transform failures into learning opportunities and strategically transition to avenues that promise more possibilities.

From her Joyus journey, Singh Cassidy gathered valuable insights into the challenges of balancing multiple ambitious goals. Joyus didn't just have to generate premium video content. The company also aimed to swiftly enlarge its customer base while effectively pricing the fashion items featured in the videos for these new consumers. These multiple, simultaneous objectives heavily complicated the path to dependable profitability for Joyus.

In your professional landscape, numerous factors can cause failure. Maybe you mistake constant activity for making a significant impact. Or you may not heed feedback and neglect to address your weak points. At times, your ambition to succeed might compel you to ignore serious underlying issues. Singh Cassidy had to confront this tendency while spearheading Google's international operations, juggling market dynamics, political scenarios, and regulatory norms of countless countries.

If you find yourself in a progressively worsening situation, rely on the framework we previously outlined to continually reassess your suitability for the challenge at hand. If your contributions and more importantly, your learnings stagnate, it might be time to search for a new challenge.

But before you tender your resignation and step out, here are a few pointers to ensure that your exit opens up more opportunities. Firstly, don't mentally check-out before officially leaving. Devote your maximum effort to your team till your final day. Prepare your colleagues for success. Share your insights and don't leave behind a mess.

Additionally, don't linger around just to collect your paycheck once your task is completed. Remember, the people you've collaborated with will continue to influence your future opportunities. So, make your move strategically.

The genesis of true power lies in choice and altruism.

In the year 2015, Singh Cassidy tapped into her network, reaching out to fellow women who, much like herself, were influential figures in the tech industry. She had a groundbreaking venture in mind.

The tech arena was embroiled in discussions surrounding gender and equity. Singh Cassidy was well aware that women were achieving success in tech despite facing bias and harassment. However, she observed that one aspect of power remained inaccessible to them: the boardroom.

Male CEOs, when questioned, often claimed that there were insufficient qualified women to occupy board positions. Singh Cassidy intended to debunk this assertion, thereby initiating new growth and opportunity cycles for women in the tech industry.

The primary insight here is: True power originates from choice and benevolence.

In that year, Singh Cassidy established theBoardlist, a talent marketplace designed to assist tech leaders in endorsing and connecting with women for leadership roles. Starting with 600 names, the platform now hosts over 16,000 qualified members.

Through the act of creating opportunities for others, Singh Cassidy stumbled upon the most significant project of her career. She realized that genuinely powerful individuals channel their power towards those around them.

This is a lesson she learned from her father, who she still regards as the most powerful person she has ever known, despite being in close quarters with high-profile business professionals for decades.

Singh Cassidy's father migrated from a different part of the world to rural Canada. He consistently chose possibilities and empowered others wherever he went. Sometimes, his acts were substantial, such as when he rallied local doctors to set up a walk-in clinic for their town in Ontario. Other times, his deeds were small yet equally impactful.

Once, a man named Bobby shared with Singh Cassidy that he had sought her father's advice during a period of intense self-doubt when he was younger. He confided in her father about his aspiration to be a doctor but his apprehensions about not being good enough.

Singh Cassidy's father held Bobby's hands, looked him in the eye, and assured him that he had the hands of a surgeon. According to Bobby, this conversation provided him with the courage he needed to pursue his dream.

Power often begins on a small scale. You can offer a word of encouragement, pen a recommendation letter, or let others bask in the spotlight. The power that you exhibit by choosing possibility and then sharing it is renewable. And it is invincible because it stems from within.

Concluding thoughts

Risk is an inevitable part of life, presenting itself as an uncertain yet fertile field of possibilities. It is omnipresent. However, when we approach it with modesty, wisdom, and kindness, we can catalyze perpetual cycles of growth. If there is one sentiment to etch in our minds, it is not to suppress our fears. On the contrary, we should identify, delve into, and address them. Doing so will pave the way to a universe brimming with opportunities.