Choose Possibility

Choose Possibility

Take Risks and Thrive (Even When You Fail)

Sukhinder Singh Cassidy

Summary in 100 words or less

Risk-taking is not a single leap that has the power to make or ruin us. Instead, it's small choices that, when string together over time, produce an impact and insight for the future. To act, your fear of missing out on opportunities must exceed your fear of failure. Even if things don't work immediately, they may resolve in your favor over time, as long as you keep choosing the next possibility and learning from the current one.


My Highlights

When you’re succeeding, never think you’re as good as everyone is telling you that you are. And when you’re failing, never think you’re as bad as everyone is telling you that you are.

The power in risk-taking lies in stringing together many choices over time, some small, some big, but each producing impact and insight that inform our future choices.

Understand that having choices in life is a privilege, and if we’re fortunate enough to have them, we should exercise them.

Any risk carries uncertainty, but if you believe everything rides on a single big choice, the prospect of uncertainty magnifies your unease.

Leaders who reach the top job more quickly than others “don’t accelerate to the top by acquiring the perfect pedigree. They do it by making bold career moves over the course of their career that catapult them to the top.” These moves include taking a smaller job in order to gain new skills or experience, taking on a job for which they felt unprepared, or signing up to tackle a big, uninviting business problem.

When we find ourselves in a stable or positive place, risk-taking serves as an accelerant that we can use to discover new opportunities, unlock new learning, or achieve an ambitious goal.

Taking small risks before committing to a given path also puts us into motion earlier, giving us a sense of momentum heading into decision-making and then execution.

We all have wisdom to glean from different people at different stages of our journey. Seek out a tribe of people who enhance rather than diminish your ability to generate ideas in any particular phase. Make sure they’re open to listening to your list of opportunities in an unbiased and nonjudgmental way, and to contributing to that list as well.

When we don’t yet know how to score ourselves, getting onto the field and closer to those who do (and have already) can teach us a lot of what we need to know, including insights we didn’t even realize we needed to learn.

When we insert ourselves into environments where people with ambitions similar to ours have succeeded, we increase the odds that we’ll access more opportunities to advance our ambitions simply by virtue of our proximity to them.

A whiteboard plan is a living, evolving thing — the opposite of the Perfect Plan. Its mere presence reminds us that the most relevant plan is one that we can alter, modify, update, or erase altogether as we gain more insight.

If our fear of missing out on opportunities (FOMO) exceeds our fear of failure (FOF) in trying something new, we’ll act. Otherwise, we simply won’t.

Rather than turning away from our fears, we move through them and begin identifying the choice-after-the-choice. That is, we visualize what we would do to recover from loss or minimize its impact after a failure occurs. We might find that we have one good follow-up choice, or several. The more we come to realize that failure won’t destroy us and that we can spot multiple options for getting back up on our feet, the less scary failure seems.

There are generally three kinds of risks we face in any career choice: financial, reputational/ego, and personal. If one of our career choices goes sideways, it’s because we might lose money, we might experience a hit to the image that we have of ourselves or others have of us, or we might lose something we value deeply on a personal level (work that gives us joy, or time spent with our family).

It’s all too easy to lump our fears together when making choices, which makes them seem bigger and more powerful. Separate them out, and you can take steps to mitigate some of them.

Small risk-taking can build our tolerance for handling all types of outcomes, instilling an experimentation mindset, but managing through a larger failure can prove far more positive and empowering than we realize, reducing our FOF going forward.

Always recognize that “who” we align ourselves with influences our ultimate success far more than the “what” we have picked to focus on. Don’t be so sure that falling in love with a given field, job type, or industry will take you most quickly to the mountaintop. Pay much more attention to the individuals who will accompany you on the journey.

Good leaders attract smart people and can sell a vision that attracts them to sign on. Great leaders are true talent magnets, surrounding themselves with people who are equally smart, confident, and diverse in their capabilities. Further, great leaders can retain these people and leverage their expertise. When you see a strong team of people who debate, disagree, but reconvene repeatedly in good spirits, you can be pretty sure that their leader knows how to develop, harness, and mobilize their skills.

If a leader shares underlying values with us, we’re more likely to understand and respect them. In turn, we’ll be more likely to stick around long enough to make meaningful contributions, deal with their quirks, and still learn the utmost.

Recruiters today rank flexibility and resilience in new hires among the most attractive traits, and headwind situations allow us to build and demonstrate these skills in ways we otherwise might not.

If we can identify not just our passions but our values and strengths, we can make better choices that take full advantage of who we are, increasing our odds of success. We can find the roles and environments that allow us to maximize our own intended results.

To accelerate your success, you need to double down on what you’re great at and to stop doing what you’re bad at.

We’re best positioned to succeed when we’re more self-aware and honest about our abilities, not less.

If you find yourself intuitively excited or fearful about a certain choice relative to others, explore why by identifying and rating the variables in the risk-taking equation. Quite likely, you’ll connect your inner hunch with one of these variables and the rating you provide.

Even if the initial results of a certain decision you’ve made don’t work out immediately, over time and multiple moves, they may resolve in your favor, so long as you’re prepared to keep choosing the next possibility and to learn from the current one.

Milestones motivate us, allowing us to pursue smaller goals and celebrate their accomplishment on our way to something bigger. Practically speaking, it’s also almost impossible to achieve outsize results in one fell swoop. We must deliver smaller outcomes first and then make the most of the momentum they create to advance our progress.

While we’ve been trained in our careers to value only positive results, the truth is that negative outcomes often advance us toward our goals as well, and deliver impact, too, by helping us to see which actions of ours worked and which didn’t.

The best truth-seekers strive to make it safe for people to give voice to their true opinions for the team’s benefit, without experiencing any negative consequences.

What today’s companies really seek is deep expertise and a breadth of perspective. As business conditions become ever more dynamic and complex, we should strive to develop deep specialization as well as a set of diversified experiences in which we broadly apply what we know and keep learning to adapt and expand our knowledge further.

If we want to produce meaningful results, we must rein in the complexity and limit our focus at any given time to just one or two key goals, considering the likely tradeoffs between them.

It’s tempting to downshift our efforts once we’ve decided to move on, dreaming of what’s next while shortchanging our current goals. But finishing well means completing what you’ve started and making good on your promises to your team or company.

One can never entirely predict how any single choice will work out. Still, if we’re willing to keep successively choosing, acting in ways that achieve impact, learning from our mistakes and the conditions around us, and allowing our hard-won wisdom to inform our next choices, we’ll experience more and higher peaks in our careers.

To put yourself on a trajectory toward a great career, choose repeatedly and deliver impact consistently, worrying less about whether you achieve success in any individual move. Over time, as we get smarter about choosing and achieving impact, we want to make sure that even if we don’t achieve all our bigger ambitions, we can still generate more positive than negative outcomes and contributions over a large body of choices.

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