people in board meeting

Years ago when I was building my 18-year corporate marketing career which culminated in a Vice Presidency, I’d read articles advising professionals to “embrace risk!” and “take chances.” But in my personal experience, I didn’t feel encouraged at all to take risks, either in my own work projects or in my career as a whole.

Instead, what it seemed my managers and leaders wanted to see was big success without any potential downside, risk or failure. Now, as a career coach to many mid- to high-level professional women globally, I see the exact same phenomenon—leaders, managers and individual contributors want to believe they are comfortable with risk-taking, but the vast majority shun it.

Smart, well-considered risk-taking is essential to our growth, and to exponential success and strong performance and leadership. So what do we have to do to expand our comfort with risk, and our willingness to take important risks in our roles, careers and organizations, and why do we need to?

To learn more about this important topic, I recently caught up with Sukhinder Singh Cassidy, a leading technology executive and entrepreneur, board member, and investor with 25 years of experience founding and helping to scale companies, including Google, Amazon, and Yodlee. Most recently, she served as president of StubHub and as a member of eBay’s executive leadership team. She is the founder and chairman of theBoardlist and has been profiled in Fortune, Forbes, The Wall Street Journal, Business Week, and The New York Times, among others. She has been named one of Elle’s Power Women, one of the Most Creative People in Business by Fast Company, and one of the Top 100 People in the Valley by Business Insider among many other accolades. She is the author of the new book, Choose Possibility: Take Risks and Thrive (Even When You Fail).

Here’s what Singh Cassidy shares:

Kathy Caprino: Sukhinder, since you focus on the importance of taking risks in your new book, can you explain the role that risk-taking played in your professional trajectory?

Sukhinder Singh Cassidy: In my career, I’ve taken risks of different sizes (small, medium, and large), but I’ve taken them consistently over the last 20 years. While single risks may or may not have worked out the way I imagined, overall, the practice of repeatedly taking risks has unlocked cumulative reward and career success.

I pursued risk-taking for various reasons, including discovering opportunities, learning something new, achieving ambitions, and even avoiding harm. I took risks when making a big career choice. After making a move, I needed to take additional risks to try and maximize the impact I had in the new role. What I learned in my career is that it was the practice of continuous risk-taking—what I call “choosing possibility” repeatedly—that led to compounding benefits.

Caprino: What advice do you have for recent college grads who are risk-averse?

Singh Cassidy: To recent college grads, I would say let go of the “Myth of the Single Choice.” The idea the one single and perfectly orchestrated choice is the key to success is a fallacy.

Instead of increasing the pressure we feel to “choose perfectly” or otherwise “fail miserably,” we can take comfort in knowing that there are ten, fifty, a hundred, or even more choices to be made to unlock the reward. What matters most is that we get into motion, understanding that we will face many opportunities and choices.

In turn, you will unlock more impact once you can execute a possibility and learn from it. Risk-taking should be regarded as the opposite of “one time, big, and binary” and instead as a continuum of choices and impacts, some of which are smaller and some of which may be larger but all of which have value.

In addition, according to a study done by LinkedIn, our chances of becoming a successful senior executive increase when we embrace diverse functional experiences to expand our learning versus one true and “linear” functional path to success. So, while we may think that sticking to one known thing is the way to get to leadership, taking risks to expand our capabilities and knowledge is a richer path to this goal.

Caprino: How is career risk-taking relevant now more than ever?

Singh Cassidy: The pandemic and changes to society, businesses, and the world of work taught us two important things:

1) Whether we seek to embrace risk-taking or not, risks will still happen “to us,” and so learning how to handle risk has value in a world that continues to face disruptions, small and big. In fact, the most dangerous thing of all is often staying still or refusing to adapt in the face of rapidly changing situations.

2) The more positive takeaway is that during the Covid-19 pandemic, we also learned a lot about our own agility and resilience. We are much more capable of flexing and discovering new ways to work, and have more impact than we might previously have thought ourselves to have. Both these factors make embracing risk-taking in our careers more relevant than ever.

Caprino: How did the hurdles you encountered along your career path make you a better worker today?

Singh Cassidy: The hurdles in my career helped me find strategies to cope with the fear of failure, or failure itself, and get into recovery mode after a choice I made did not work out the way I imagined. As a result, I gained agility and—ironically—more confidence to try new things, not because of massive success, but from solving my way out of a failed situation.

These two traits have made me comfortable taking more small risks on the job to try and accelerate my impact, with less fear of looking stupid or worry that I won’t be able to cope with a negative result. I believe that everyone can do great work, but part of what holds us back is our negative self-talk about our ideas and perception that we need to appear perfect to others. Facing hurdles helped me face my own imperfection and understand my ability to drive progress once I gave up striving for perfection in favor of learning or executing faster.

Caprino: From your view, what are the most integral values a manager needs to grow their employees and why?

Singh Cassidy: To grow our employees as managers, we ultimately need to give them the safety to take risks on the job to accelerate their own impact and contribution.

This means cultivating an environment that welcomes:

Authorship – where people can create their own vision and drive it versus just adopting ours

Diversity – where new ideas and debate are sought out and exchanged to make a project stronger, not weaker

Authenticity – where questions can be asked, and truths told that help everyone learn faster in an environment where candor and constructive feedback are encouraged

If we can create these environments for our teams, they are likely to take more little risks at work to accelerate their own contribution. As a result, the team’s collective chances for success will soar.

Caprino: What are three steps a leader can take today to become a better risk-taker?

Singh Cassidy: To become a better risk-taker, leaders need to:

Find and demonstrate ways to take risks—small and big—consistently. Whether that’s taking ego risk by admitting in a meeting we don’t understand something or giving our teams a budget to experiment in a new area without penalizing them if they can’t produce an impact as fast as we want. Our teams will emulate what we do.

Favor rough planning and then refinement of plans as we’re iterating, versus striving for “perfect planning” before taking a single action. If we encourage our teams to be “perfect” over finding progress, we risk the organization’s overall execution and agility.

Be forthright (or “heads up”) in identifying the macro tailwinds and headwinds that can disproportionately identify the changes of success in any endeavor. Often teams are “heads down” and overweigh perfect execution to achieve any goal. Taking smart risks is also about being attuned to the macro environment and responsive to conditions around us to increase our odds of success. 

Caprino: Exactly how does taking risks expand our possibilities and opportunities in ways that wouldn’t be possible without it?

Singh Cassidy: Without risk-taking to discover new opportunities, we are constrained in the fundamental number of choices we face in any given situation. We can’t ascertain what all the possibilities might be to solve a problem or reach a goal unless we take little risks to discover the paths available before choosing. So not taking risks to discover possibility first may leave you in a position to make the riskiest choice of all: picking without knowledge.

Similarly, once we have made a big choice and are executing our way towards the larger reward we seek, we need to continue to take little risks to execute and drive a smaller outcome first.

Every one of these choices accelerates our learning and informs us where to head next, helping us to become smarter in our execution and build momentum.

This is another example of taking micro-risks each day to achieve impact and maximize the chances of success towards any bigger goal.

So, if we risk more, we’ll fail more. That’s a given; I believe.

Caprino: In career coaching with thousands of professionals I’ve seen that most people are highly risk-averse and find it terribly hard to deal with their own perceived “failures.” How do you help professionals reframe their experience of “failure” and see it as not something to shun or run away from but embrace and recognize its value?

Singh Cassidy: Many professionals I work with tell me they hear that they should embrace risk but are simply too afraid to do that, as they don’t want to feel shame, vulnerability, humiliation, etc. And professionals are often “trained never to fail.”

While folks are told to “embrace failure,” no one tells us how actually to do it.

Several strategies can help us overcome the fear of shame and vulnerability:

Take micro-risks every day

When we consistently expose ourselves to little risks, we deal with small failures that are easy to recover from. Whether that’s speaking up in a meeting or researching a new job we’ve long dreamed about, we want to give ourselves practice taking actions outside of our comfort zone to build that muscle.

Imagine the “choice after the choice”

Inevitably, we must make “the wrong” choice and recover to make a more informed choice moving forward. This imagining the “choice-after-the-choice” helps us imagine failure and all the paths available to us after.

Sometimes the best way to help get us into motion is to work through the failure in our minds and realize there is always a “next choice” or set of choices we can execute.

Continuously choosing possibility is the antidote to the myth that we need to be perfect at every single choice we make.  

For more information, visit Choose Possibility

Kathy Caprino, M.A. is a career and leadership coach, speaker, educator, and author of The Most Powerful You: 7 Bravery-Boosting Paths to Career Bliss. She helps professionals build their most rewarding careers through her Career & Leadership Breakthrough programs, Finding Brave podcast, and her new Most Powerful You course. Follow me on Twitter or LinkedIn. Check out my website or some of my other work here.


  • Kathy Caprino

    Hi! I’m a career and leadership coach, writer, and speaker dedicated to the advancement of women in business.

    Kathy Caprino, LLC

    Kathy Caprino, M.A. is an internationally-recognized career and leadership coach, writer, speaker and trainer dedicated to helping professional women  "find brave" and close their power gaps to create more success, fulfillment and reward in their lives and work. A former corporate Vice President, a trained marriage and family therapist, and the author of Breakdown, Breakthrough and the new book The Most Powerful You: 7 Bravery-Boosting Paths to Career Bliss, Kathy is the Founder of Kathy Caprino, LLC and of the Amazing Career Project online career course and the Amazing Career Coach Certification training program. She is a Senior Contributor on and leading voice on Thrive Global and LinkedIn, and a top media source on careers, women’s issues, and leadership and has appeared in over 200 of the nation’s leading publications, and on national radio and TV. Her podcast Finding Brave ranks in the top 100 Apple Career Podcasts in the U.S. and beyond, and shares compelling interviews with top business and leadership experts, bestselling authors, creatives, entrepreneurs, and thought leaders who are making a brave difference with their work. For more information, visit and, check out her new course The Most Powerful You, and connect with Kathy on LinkedIn, Twitter, Facebook and Instagram.