Metaphors exert a powerful influence on our daily decisions. For example, many of us strive to climb the “career ladder,” each step taking us closer to the top. But what if some steps represent smaller leaps than others? What if we slip off a rung or take a step backward?
Silicon Valley CEO and entrepreneur Sukhinder Singh Cassidy challenges us to reframe how we look at careers in her new book, Choose Possibility. I recently spoke to Sukhinder about her novel approach to designing a career, a tactic she adopts from design principles that have fueled the growth of famous tech companies.
Iteration is the key.
The iterative process is a well-known system that designers and developers apply to build products. In the iterative process, you create a prototype, test it, and learn from failures. Each iteration brings you closer to a product that customers will love.
Similarly, a dream career is built after taking many risks—often small and iterative. “Success comes from choosing repeatedly, not choosing once,” says Sing Cassidy. “Many people subscribe to what I call the Myth of the Single Choice. They think people are successful because they take one mighty risk. The opposite is true. A career is built over many, many choices.
Sing Cassidy advises ambitious professionals to value progress over perfection.
“Perfection is an illusion,” she says. “When people put pressure on themselves to make one perfect career decision, they move in the opposite direction of how reward really happens. The biggest risk is inaction.”
Over a nearly 30-year career, Sukhinder has remarkable results to show for the series of choices she made—not all of which were successful.
For nine months after graduating from college, Sukhinder failed in landing a job. One day, she learned about a private investment firm seeking to hire an MBA student. Although she didn’t have an MBA and very little work experience to show, she left a voice message for the hiring manager. The company invited her to participate in a rigorous six-week vetting process alongside MBA grads with more experience.
Ultimately, Sing Cassidy didn’t get the job. But what she learned was invaluable.
Recruiters were impressed with her communication skills which sparked a decades-long dedication to sharpening the way she presents herself. The small risk that Sing Cassidy took by applying for a stretch job resulted in “failure” in one sense, but a success in another. The fact that she nearly won the position gave Singh Cassidy “a sorely needed boost of confidence,” which she soon parlayed into a job at Merrill Lynch where she worked as an analyst for four years.
Fast forward nearly thirty years later. Singh Cassidy has started three companies, taken one public, served as CEO of two others, and advised some of the largest tech companies (Google, Amazon, and others). Most recently, she served as president of StubHub, which she led to a multibillion-dollar sale.
Singh Cassidy estimates that she has made 23 career choices over three decades. Some worked out. Others didn’t. But she learned to stay in motion.
“If you scrutinize the careers of successful people, you discover that success usually unfolds progressively as a result of many risks of different sizes,” says Singh Cassidy. You will also find that a person’s overall success usually arises out of multiple failures as well as wins along the way.”
Think of your career as the product of an iterative design process. While you can’t predict how any single choice will work out, if you learn something from the outcome, you’ll continue to make progress toward your ultimate destination. Above all, says Singh Cassidy, use the hard-won wisdom from your last choice to inform your next one.
Choose progress over perfection and risk over inaction. That’s the Silicon Valley formula to building the career of your dreams.