What will I learn about: why true make-or-break moments are rare and how reframing risk as a series of small, evolving choices can help you unlock new possibilities?

Understand why true make-or-break moments are rare and how reframing risk as a series of small, evolving choices can help you unlock new possibilities.

What will I learn about: how freeing yourself from the myth of the single-path 'hero's journey' and pursuing multiple low-stakes options at once will generate unforeseen opportunities?

Discover how freeing yourself from the myth of the single-path 'hero's journey' and pursuing multiple low-stakes options at once will generate unforeseen opportunities.

What will I learn about: Learn why fortune favors the physically present and how putting yourself in close proximity to your goals can reveal hidden career opportunities?

Learn why fortune favors the physically present and how putting yourself in close proximity to your goals can reveal hidden career opportunities.

What will I learn about: the crucial balance between your fear of loss and your fear of missing out (FOMO) by objectively naming your worries and assessing their true long-term impact?

Master the crucial balance between your fear of loss and your fear of missing out (FOMO) by objectively naming your worries and assessing their true long-term impact.

What will I learn about: how to confidently take big leaps by creating solid contingency plans and realizing that most major life decisions can actually be undone?

Find out how to confidently take big leaps by creating solid contingency plans and realizing that most major life decisions can actually be undone.

Choose Possibility

Seek Change, Take Risk, and Thrive (Even When You Fail)

Sukhinder Singh Cassidy

★ 4.5 / 5(119 ratings)

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Categories:

Career & Success Entrepreneurship

If You're Curious About These Questions...

You should listen to this audiobook

💡Did you know that the most successful career paths aren't built on one single "big bet," but on a completely different approach to risk?
💡Have you ever wondered why some people seem to effortlessly navigate uncertainty while others feel paralyzed by the fear of making a mistake?
💡What if you could transform risk-taking from a terrifying leap into a repeatable skill that consistently unlocks your professional potential?

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Key Takeaways from Choose Possibility

✓Understand why true make-or-break moments are rare and how reframing risk as a series of small, evolving choices can help you unlock new possibilities.
✓Discover how freeing yourself from the myth of the single-path 'hero's journey' and pursuing multiple low-stakes options at once will generate unforeseen opportunities.
✓Learn why fortune favors the physically present and how putting yourself in close proximity to your goals can reveal hidden career opportunities.
✓Master the crucial balance between your fear of loss and your fear of missing out (FOMO) by objectively naming your worries and assessing their true long-term impact.
✓Find out how to confidently take big leaps by creating solid contingency plans and realizing that most major life decisions can actually be undone.

Learning Tools

Reinforce what you learned from Choose Possibility

Mind Map

Choose Possibility

Redefining Risk+

Proximity & Presence+

Managing Fear & Making Choices+

The Role of People+

Navigating Headwinds & Tailwinds+

Handling Outcomes & Failure+

True Power & Generosity+

Actionable Daily Practice+

Quiz — Test Your Understanding

Question 1 of 9

What is a fundamental misconception humans often have about risk and career paths?

A. We believe risk should be avoided at all costs to protect our financial stability.
B. We think careers are defined by single, make-or-break choices rather than multiple small risks.
C. We assume that taking multiple small risks is more dangerous than taking one large leap.
D. We trust our intuition too much when evaluating the potential downsides of a career move.

Question 2 of 9

According to the author's experience traveling to New York and later San Francisco, what is a crucial factor in seizing hidden opportunities?

A. Having a meticulously planned, long-term career strategy.
B. Being physically present in the proximity of your goals and dreams.
C. Waiting for recruiters to reach out with the perfect job offer.
D. Ensuring you have a financial safety net before relocating.

Question 3 of 9

How does the author suggest you build the momentum needed to take a leap into a new opportunity?

A. By completely eliminating all anxiety and fear of failure before acting.
B. By ignoring the potential financial downsides and focusing strictly on the upside.
C. By analyzing your worries until your fear of missing out (FOMO) outweighs your fear of loss.
D. By choosing the option that provides the most immediate financial reward.

Question 4 of 9

What lesson did Singh Cassidy learn from her brief, negative experience at the startup OpenTV?

A. Startups are inherently more risky than established megabanks.
B. When evaluating a career move, the people you work with are just as important as the job itself.
C. Passion and intensity are usually viewed as negative traits in the tech industry.
D. It is better to work independently than to rely on a team for success.

Question 5 of 9

How should a professional view the 'headwinds' or large adverse forces they encounter in their career?

A. As clear signs of personal incompetence and inner weakness.
B. As unfair obstacles that should immediately prompt a resignation.
C. As challenging situations that can provide unique opportunities to build battle-tested skills.
D. As predictable outcomes of failing to plan a career path properly.

Question 6 of 9

When evaluating a massive, high-stakes career change, what method does the author recommend?

A. Deconstructing and rating the elements of both the opportunity and the potential downsides.
B. Trusting entirely in your gut instinct, as the subconscious mind processes information best.
C. Flipping a coin, because the relationship between risk and reward is inherently unpredictable.
D. Asking your professional network to make the final decision for you.

Question 7 of 9

What does the author's experience of being ousted as CEO of Polyvore illustrate about risk and reward?

A. A big career risk will always result in an immediate, proportional reward.
B. Failing at a high-level position permanently damages your professional reputation.
C. You should never accept a leadership role in a company where the founder is still present.
D. The rewards of a risk are often nonlinear, widespread, and appear at unpredictable times.

Question 8 of 9

According to the book, what is the best way to handle your departure when you decide it is time to move on from a failing or unfulfilling job?

A. Leave immediately to protect your mental health and cut your losses.
B. Give maximum effort until your last day to tee up your colleagues for success.
C. Keep collecting a paycheck while doing the bare minimum until you find a new role.
D. Publicly air your grievances so the company is forced to address its underlying problems.

Question 9 of 9

Through her creation of theBoardlist and observing her father's life, what did Singh Cassidy conclude about the nature of true power?

A. Power is a finite resource that must be carefully guarded from competitors.
B. Power is primarily derived from holding a C-suite title or a board seat.
C. Power comes from making choices that flow generosity and opportunity to others.
D. Power is achieved by taking credit for the successful risks of your professional tribe.