Taking the Scenic Route: On Failing, Learning, and Knowing Yourself
I was a bookish child. I read during recess, lunch, and, occasionally, dinner. I would even read while walking, a habit that my parents were convinced would eventually cause my death.
For the most part, I read science fiction — with a smattering of Austen and Wilde for good measure. Asimov, however, was my true love. In particular, I enjoyed his delving into the edge cases testing his Three Laws of Robotics. Dr. Susan Calvin, a recurring character in his robot stories, became a role model of sorts. Plain, effective, and brilliant, she blazed a (fictional) path for geeky girls who relied on their brains to navigate the world.
But where Calvin was largely a misanthrope, I loved people. Driven by a desire to understand others — what makes them tick, why they make the decisions they do—and to make a positive impact on the world, I harbored childhood fantasies of a career in politics.
I dreamed about becoming the Chief Executive of Hong Kong or a diplomat for the United Nations. In one of my application essays for Penn’s Management and Technology program, I wrote a fictional page of my autobiography describing how I would bring a human touch to technology-enabled diplomacy, choosing to learn and speak a foreign language rather than rely on instantaneous translation devices.
In college, I realized that politics was probably too dirty of a game for me to play. My temperament — earnest, cerebral, principled — was wholly unsuited for trading in my ideals for power. I recall a negotiation class where the vast majority of my classmates identified their negotiation style as pragmatic idealism; I forcefully made the argument that the very phrase was an oxymoron. Idealism is a pure state. The moment you taint it with pragmatism, you enter the gray zone, at which point you are merely debating the degree, not the fact. A pragmatic idealist is one who wants to feel good, rather than face the reality of their pragmatism. Some people seemed to take that declaration rather personally, but my professor congratulated me for the intellectual honesty.
Upon graduation, compromising between my parents’ wishes and my personal interests, I joined an exciting team at Capital One that was led by a Penn M&T alum I admired. However, shortly afterwards, he left for PayPal. Stuck in an industry I had no particular affinity for and deciding that I would make my next career move based on industry, not personality, I was fortunate to receive a referral from a former Capital One VP to his current employer — Google.
I thrived at Google, both professionally and personally. I won awards, worked on products used by millions, and led initiatives that were near and dear to my heart. And yet, I wanted more. After a few years, I found my initial enthusiasm waning, no longer certain whether I was having the kind of impact I wanted to have on the world. I felt like a cog in the machine, easily replaced by any other reasonably intelligent person. It was getting harder to drag myself to work each morning. I may have been depressed.
You could call it a quarter-life crisis.
Clean tech, ed tech, you name it, I probably looked at it. Nothing seemed worth leaving Google for until I came across this crazy opportunity to join a social enterprise startup accelerator based on a ship traveling through Southeast Asia with the Archbishop Desmond Tutu, winner of the Nobel Peace Prize, along with amazing mentors such as Megan Smith (then Google VP, now United States CTO).
My course was set. I would travel down the path of social entrepreneurship, enabling technology-driven startups that would better the lives of others. It would be a grand adventure. The idea captured my imagination. My then-girlfriend (now wife) expressed misgivings about the distance but was otherwise supportive of my following my heart.
What ensued can only be described as a tragicomedy of errors. Without naming names, I can only say that I learned two very important lessons:
- Not everyone in social entrepreneurship is a Nelson Mandela, by which I simply mean that you will find every kind of person in every industry. Working in social enterprise does not automatically mean that motivations are pure or that characters are principled. Fawning magazine profiles are the worst.
- Social entrepreneurs are not necessarily great entrepreneurs. This is probably even more obvious than the first lesson, but having good intentions does not automatically confer upon the individual the ability to run a thriving business.
By the time I disembarked the ship, I found myself jaded and cynical. I met up with my partner in Germany for one of her robotics conferences and we traveled across Scandinavia. I continued my journey in Asia, spending some time on a commune in India, visiting family in Hong Kong, and hiking through Bhutan. To cap off my soul-searching as a living, walking, breathing cliché, I returned to Burning Man before coming back to San Francisco.
The siren call of Silicon Valley still beckoned.
I explored my options at VCs, corporate accelerators, and fledgling startups. Trying to make a final decision, I exchanged emails with a former colleague who landed in VC:
I went with my gut and chose to work with Drew Patterson, a serial entrepreneur with deep industry expertise and a couple of successful exits under his belt. It was a good ride while it lasted (the startup was acquired earlier this year) and I learned some valuable lessons:
- Startups are hard. Past performance does not guarantee future success. Current performance does not guarantee future success.
- One bad hire can throw you way off course. And you might not find out until a year too late. Check references thoroughly.
- Cash is king. Keep burn low. Revenue is useless if you can’t collect it.
- Enjoying the act of traveling does not mean you should work in the industry. Margins are pretty low. To everyone who thinks their love of travel qualifies them to launch a successful startup in the space: you’re most likely wrong.
- Find your tribe. Look at who your friends are (mine mostly consist of engineers and STEM PhDs, as well as a select group of fine dining nerds) and see if your coworkers fit the mold.
After the startup, I started working on a little Android app for my wife, an award-winning roboticist who forgets to keep in touch with her friends. Writing code again — for the first time since college—was humbling and intellectually invigorating. It was also frustrating: I didn’t know what I didn’t know and, as a result, I made a number of rookie mistakes that caused me to have to rewrite my code from scratch. But it was also deeply satisfying to work on a technical challenge that I found personally meaningful.
Perhaps most importantly, I discovered that time heals all wounds. Slowly, but surely, my return to San Francisco after leaving the ship infused me with a renewed sense of optimism. There are still good people doing great work on hard problems that concretely impact the lives of millions—and I’m not talking about mobile apps that complete chores your mother used to do for you. Sure, there will always be the youth-celebrating vanity lists (it’s good for page views!) and the self-congratulatory conference circuit, but if I dig beneath the surface, there is so much potential. So much hope (albeit tempered with some hard-earned wisdom). And if I could just find that perfect intersection of what I love, what I’m good at, and what the world needs and will pay me to do…
I’ve always had trouble reconciling my brain with my heart.
During one period of confusion many years ago, I found myself looking at brochures for divinity school. I briefly flirted with the idea of becoming a religious thought leader until I realized how patently ridiculous the idea would be, given my agnosticism. I occasionally joke about how I would be a great missionary if I were actually religious. If I had something to believe in.
Well, now I do.
With the time, space, and freedom to introspect — a rare privilege, I know—I gathered all the disparate threads of my life. My love of science fiction and fascination with cutting-edge technology. My desire to meaningfully impact the life of another human being, ideally at scale. My yearning to be part of something new, where the answer is still unknown and I am in the vanguard of discovery. My tendency to surround myself with engineers and scientists. My politics, my ethics, my values.
So this is the culmination of my experience to date, an amalgamation of the opportunities I have been given and the people who have touched my life:
I believe that robots will fundamentally change the fabric of society — economically, socially, and politically (also an essay for another time). I believe that robots can positively impact the human condition, but that we must thoughtfully consider where and how to deploy them. I believe that robots are still in their infancy, in many ways, but they are an inevitable part of our future.
And so, I have officially joined SoftBank Robotics, which launched the first commercially-available social robot, to lead platform and serve as a robot evangelist. I’m thrilled to join the team and be part of this story.
My pen is ready. The next chapter should be fun to write.
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Cynthia Yeung has criss-crossed the globe working for Google (where she won an OC award along the way), a social enterprise startup accelerator on a ship (which counted the Archbishop Desmond Tutu and US CTO Megan Smith as mentors), and a travel startup (led by a member of the KAYAK founding team). She was invited to the White House LGBT Tech & Innovation Summit and, as an INFJ, she spends a lot of time thinking about interpersonal relationships.
She currently works for SoftBank Robotics, is married to a roboticist, and occasionally finds herself editing robotics research papers (for love).
