Talking Risks: A Chat With the Fear‑Bending Exec
New York, Aug 24 – If you had to cherry‑pick a single word that sums up the pandemic era, “risky” would be a sharp contender. In a world where health, careers, and wallets feel like they’re on a tightrope, Sukhinder Singh Cassidy drops some golden nuggets.
Who’s Sukhinder, Anyway?
A former powerhouse at StubHub, Google, and Amazon, she’s just unleashed her latest book: “Choose Possibility: Take Risks and Thrive (Even When You Fail)”. Her big question? “How can you let risk be your wingman?”
Q: Do people need to double down on risk in the office?
A: People hate failure, rejection, and looking like a zero. That ego‑driven dread keeps folks playing it safe at work. Let’s face it—fear of judgment is the loudest blocker.
Q: Is this the perfect time to throw caution to the wind?
A: COVID forced us to tighten our belts, but it also taught us how slick we can be at moving fast. When calamity hits, we’ve proven we’re good at pivoting—so why not rinse and repeat during the good times?
Q: Risk is like a muscle—tell us why.
A: The myth? Some people are born to risk. Reality? Anyone can flex this muscle. Keep adding tiny reps—small risks every day—and you’ll learn what works. Even if things mess up, you’ll have shrugged off that scary “failure” spell.
Q: Why go for several risks at once?
A: We’re wired to chase one goal after another, which stalls progress. Pulling in multiple risks diversifies your chances and opens up a toolbox of options. If you’re clueless about what you want, the only way to figure it out is to try a bunch of stuff.
Q: Isn’t staying risk‑averse safer?
A: That’s a career hazard. Your skills can evaporate 50% every five years. Sticking still is like missing the escalator. If everyone else’s moving, the abyss of stagnation grows.
Q: Working moms feel the heat—what’s your advice?
A: The big gamble is asking for what you need. Back when I was running an international team at Google and got pregnant, I spoke up for a nanny and travel reimbursement. The company obliged. Winning starts with credible track record—ask confidently.
Q: Silicon Valley’s “tech bro” vibe—any words for women?
A: Find a crew that vibes with your values. Bias is real; some folks feel it more than others. Company culture matters. When you feel secure, you’ll speak up and negotiate the support you deserve.
Q: Is failure part of the playbook?
A: Tick yes. Calculated risk‑taking means riding failure and success alike. Careful choices over time create a high win rate, letting you reap the sweet spot between risk and reward.
Author’s Takeaway
“Choose Possibility” reminds us that risky moves keep us honest, agile, and alive. Strap in, take a bite, and—if you’re lucky—it’s a flavorful journey.
