Choose Possibility Book Summary By Sukhinder Singh Cassidy

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Choose Possibility is a must-read book for those looking to build their risk-taking skills and unlock their professional potential.

It's written by tech leader Sukhinder Singh Cassidy who has lived and breathed risk in her winding path through business, and she shares her insights with others so they can make similar strides in their own lives.

The book focuses on debunking the myth that life-altering decisions are the only kind of risks worth taking in life.

Instead, it looks at risk as a continual process that can be honed just like any other skill.

Through this book you'll learn how to identify risks accurately, how to evaluate them objectively, how to weigh your odds of success before taking on a challenge, and more - all of which take practice but that can ultimately lead you down the path towards greater success.

Choose Possibility Book

Book Name: Choose Possibility (Seek Change, Take Risk, and Thrive (Even When You Fail))

Author(s): Sukhinder Singh Cassidy

Rating: 4.6/5

Reading Time: 28 Minutes

Categories: Career & Success

Author Bio

Sukhinder Singh Cassidy is an expert in the tech industry with decades of experience, as well as founding, building and guiding a number of big companies including Google, Stubhub, Amazon and more.

She's renowned for her success in bringing success to her businesses and currently serves as chairperson of theBoardlist - a platform that offers an even bigger and more diverse pool of talent to companies across the world.

Sukhinder is the perfect author for her book - Choose Possibility - which focuses on helping readers find success in business.

How To Embrace Risk With Intelligence And Generosity

Risk With Intelligence

Too often, when we think about the choices that may define our lives, risk can become overwhelming and even terrifying, causing us to shrink away from committing.

But Choose Possibility, written by acclaimed author, is here to remind us that although life-altering decisions exist, true make-or-break moments are rare.

This book explains how instead of dreading risk, we should look at it as an ongoing state of opportunity and uncertainty whose possibilities can be unlocked with intelligence and generosity.

In Choose Possibility, readers will learn how to handle their careers’ headwinds and tailwinds, balance fear of failure against fear of missing out, and gain a better understanding of power to help them embrace risk more confidently.

In a nutshell: if you want to unlock possibility in every situation and make your own opportunities in life, then you can jumpstart the process by learning to embrace risk with Choose Possibility.

Free Yourself From The Hero’S Journey And Pursue Multiple Options At Once

In our culture, we often place heroes on a single path and assume that they must conquer one great feat in order to be successful.

However, the truth is that achieving success involves facing many small choices and risks.

This is where Singh Cassidy found herself after college.

She had taken all the right steps: applied to big firms, took the LSAT, but still no job offers followed.

In this moment of despair she realized that she had been confining herself to the ‘hero’s journey’ – putting her entire fate in a single choice and pigeonholing her career path.

Instead of giving up on her dreams entirely, Singh Cassidy chose to take what she calls “multiple, small risks” which opened up new possibilities for her.

She started a low-level bank job and opened herself up to med school applications and foreign service examinations at the same time.

This insight led her to get a train ticket New York City which changed her life forever.

The Power Of Proximity: How Embracing Risk Can Lead To Unexpected Opportunities

When it comes to achieving success in life, fortune favors those who are physically present.

That is something which Singh Cassidy quickly learned when she got an invitation offer a full-day tryout for a position as an analyst in New York City from a rejection letter from the major bank Merrill Lynch.

Her father quickly recognized the potential for this opportunity and bought her daughter a train ticket on the spot.

This one act of being physically present changed Singh Cassidy’s life as she was eventually offered the job at Merrill Lynch and decided to leave her hometown of Canada for NY and, subsequently, London.

It was here that through networking with different people, she heard about the tech boom happening in California leading her to purchase a plane ticket and follow her dreams of setting foot in the Silicon Valley.

This example highlights how being present can be crucial towards finding success in life.

While planning one’s career is important, embracing risk could be a faster way to reach professional goals – like what happened to Singh!

A study conducted by LinkedIn even found that high-level consultants and CEOs rise faster when they follow winding paths filled with risks over following step-by-step instructions laid out by plans.

Conquer Your Fear Of Loss And Fomo To Take Action And Achieve Success

Fear Of Loss

When it comes to taking calculated risks and seizing opportunities in life, there’s one obstacle that often gets in the way: fear of loss.

This is especially true when we’ve invested a lot of time and money into something, as was the case with Dr.

Nicky Cassidy’s optometry business.

She knew she had to make a change to keep her business afloat, but feared losing all the money she had invested in equipment, having to leave behind loyal customers, and letting go a roster of devoted employees.

However, if she could just summon up enough courage to face her fears head-on, then she’d be able to take the leap towards success.

But how? The answer lies in first looking hard at what it is you’re scared of.

Ask yourself: Am I afraid of financial loss? If so, what exactly do I stand to lose? Or am I worried about professional or personal damage if things don’t go as planned? Taking some time to analyze these worries can help you better understand your fears and adjust their balance accordingly.

It also pays off tremendously to try and imagine how things might look like over time; will they still seem this big in three years’ time? Think realistically: if worse comes to worst (which it seldom does), is this really something that cannot be undone? In such cases, drawing up a contingency plan can help protect against any lasting damage.

Just like Google engineer Alan Eustace did before his record-breaking jump from the stratosphere by running 250 tests on his jumpsuit – until eventually his FOMO outweighed his fear – you too can overcome your fear of loss and bravley take the leap forward!

It worked for Nicky; after facing her worries head-on, pursuing multiple low-stakes paths and finally reacting quickly when an opportunity came along with potential – she lost her optometry practice but regained much more than that; namely her life which she eagerly started anew!

The Key To Success: Find Your Professional Tribe And Nurture Them

Making the right career move is not an easy decision, and there are many factors to consider.

But when it comes to evaluating a potential job or company, Singh Cassidy reveals an important piece of advice: tip the scales in favor of people.

This advice has been invaluable throughout her own career and it’s something everyone should take into account when they are looking for their next move in life.

Firstly, ask yourself, what kind of colleagues do you have? Do you feel inspired by them? Will they bring out the best in you? If the answer is yes, then this could be a great opportunity.

On the other hand, if working with a certain type of people doesn’t excite or motivate you in any way, then it’s worth considering another move.

Of course we all need to make money – but feeling energized and inspired by your co-workers everyday is equally important too!

Ultimately, pursuing meaningful work with inspiring colleagues can turn a mediocre position into an exciting challenge that keeps you motivated for years to come.

Know Yourself And Recognize When You’Re Fighting Headwinds To Ensure Success


The key message to consider when looking for success is: know yourself, and know what’s out of your control.

Too often we look at success as something one achieves due to their individual skills and hard work – which are obviously factors, but there are other influences at play too.

Take the example of Shanti Singh Cassidy who took a meteoric rise through the tech boom of the late 1990s and early 2000s.

She worked her way up from manager to founder then joined Google working on Google Maps, showing her remarkable talent.

However, it wasn’t just down to her talent that got her this far – she was also influenced by the forces of history, getting lifted along by favourable tailwinds in the booming tech sector.

At other times though, success can seem so much further out of reach due to large headwinds: forces which doom projects before they start.

This was true for Jane Fraser when she took the helm at Citigroup amidst a Latin American banking collapse and subprime mortgage crisis.

It’s important then not to take failure as a sign of weakness, but instead recognise you’re dealing with historical forces outside your own control – still though these tough circumstances can provide unique professional growing opportunities, building your resilience and preparing you for future successes.

Don’T Take Big Risks Blindly: Learn To Analyze Them Carefully For Maximum Benefit

We’ve seen just how powerful it is to use the tools we’ve honed while facing smaller risks when tackling bigger ones.

The principles of risk taking still apply – we just need to deconstruct and rate our fear of loss as well as our fear of missing out.

Start by making a list of each element involved and prioritize them accordingly.

Factors such as fulfillment, fit with personal values, strengths, weaknesses, other people involved and the headwinds and tailwinds should be considered when measuring the opportunity you have in front of you.

Next step is to recognize potential financial harm, reputation or ego damage– basically any personal loss that might result from this decision.

At this point ask yourself if it’s a two-way door, are your choices reversible? Do you have a backup plan? If so then score each factor based on their risk level.

Even after doing this methodically, you’ll often feel your gut telling you something else that doesn’t make sense logically.

Don’t ignore it but don’t just follow blindly either.

When your mind and intuition quarrels test both against data until you find a solution that satisfies them both.

The Power Of Taking Risks And Reaping Big Rewards (Despite Setbacks)

As CEO of Polyvore, Singh Cassidy was humbled to come in and take the baton from its founder.

Little did she know that their visions for the company would ultimately clash.

She acted quickly by setting up open lines of communication – like regular coffee dates – in order to build a rapport of honesty and respect with her predecessor.

However, despite her efforts, the end result was being let go from the job.

At first this seemed like her biggest professional failure but in hindsight silver linings emerged as a result of this unexpected move.

This episode taught Singh Cassidy an important lesson about risk and reward; their relationship is nonlinear and often unpredictable.

For example, while she initially lost the job positions at Polyvore, benefits such as new professional connections, gaining knowledge, and having inside scoop on investments appeared later in surprising ways and led to eventually starting her own e-commerce platform Joyus.

Though it may be hard going into risky projects with no defined outcome straightforward away, these opportunities can still be beneficial when approached smartly over time as results are often widespread and arrive unexpectedly later on in various forms.

Learn From Failure And Move On To Create More Opportunities


Failure can teach many invaluable lessons, and it’s important to recognize when failure is the right time to move on.

Such was the case for Singh Cassidy, whose fashion commerce start-up Joyus saw beyond doubling of revenue year over year, yet wasn’t able to balance these increases with production costs.

After six years of hard work and small successes, before the startup sold to another company its potential had gone unfulfilled.

From Joyus, Singh Cassidy learned how to identify an unsustainable situation; her team was trying to both rapidly expand their customer base while producing high-value video content that let users shop directly from within the video player – essentially balancing two or more large goals.

She learned that sometimes a desire for success may stifle our ability to cnfront difficult underlying problems in need of solving.

This lesson applies not just in business but also in your own professional life: when struggling with a deteriorating situation it’s crucial that you are honest with yourself as to what you stand to gain from staying put.

If your impact as well as your personal growth remain flatlined, then it may be time to look for something new.

But before saying goodbye make sure you give your maximum effort until the very end and lay good groundwork for those who remain!

By learning from failure and taking steps which create more opportunity rather than resigning ourselves to stagnation we all have the best chance of fulfilling our potential!

The Power Of Choosing Possibility And Sharing It – How Singh Cassidy’S Father Inspired A Legacy Of Empowerment

In 2015, when tech was facing a debate over gender and equity, former tech leader Sukhinder Singh Cassidy had an idea.

She wanted to challenge the notion that there weren’t enough qualified women to fill board positions and create opportunities for more women to join tech leadership roles.

To achieve this, she developed theBoardlist – a website designed to connect tech leaders with women aiming for executive or board positions.

At the heart of Singh Cassidy’s mission is the underlying belief that true power comes from choice and generosity.

Prioritizing possibilities and promoting the successes of others are meaningful paths to unlocking one’s own power.

This message carries particular weight as it draws on lessons learned from her own father – a man she considers one of the most powerful people she has ever encountered.

Despite his success in business, he spent much of his time lending support to those around him: creating walk-in clinics, offering words of encouragement, advocating for seeking out possibilities and extending the spotlight onto someone else with potential.

By embracing this mindset of choice and generosity instead of hoarding power for oneself, we can pass on limitless opportunity to others; empowering them to pursue their dreams without hesitation or doubt.

Power starts small but each act is an investment in sustainable change — an example worth aspiring towards in our pursuit towards making real progress in tech industry equity.

Wrap Up

The theme of Choose Possibility by Holger Urs Muller and Susanne Fink is that risk can be a positive force and should be embraced with humility, intelligence, and generosity.

The book also emphasizes the importance of not denying fears and instead exploring them in order to open up new possibilities.

In terms of actionable advice, it encourages readers to take small risks on a daily or weekly basis in order to gain strength and courage.

Small acts of bravery will accumulate over time, making it easier to make bigger leaps when necessary.

By taking risks, readers will be able to uncover new opportunities and continually grow as individuals.

Arturo Miller

Hi, I am Arturo Miller, the Chief Editor of this blog. I'm a passionate reader, learner and blogger. Motivated by the desire to help others reach their fullest potential, I draw from my own experiences and insights to curate blogs.

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