Take a Risk on the Road Less Traveled

In May 2018, I joined AutoGravity as its first general counsel. Starting this new position was one of the biggest career risks I have ever taken.

As a second-generation, Gen-X, Japanese-American raised in middle-class Gardena, California, it was ingrained in me that success and stature were synonymous with attaining a high-level job at a name-brand company. I worked hard to get there, earning degrees from prominent universities and working at companies with established names.

Then, I found myself at a crossroads. It came in the form of two job offers—one, from an established, global company, and another, from a fintech startup named AutoGravity.

I paused and thought to myself: Should I take the safe, stable route, or the road less traveled—at least by me?

“What ifs” swam through my head. What if I weren’t the right lawyer for a startup? What if I didn’t have the flexibility and adaptability to handle it? What if I couldn’t excel at this job, while still being an available parent to my daughter, as well as a supportive spouse?

I called upon my lifelines, including a trusted mentor. She advised me to find what made me uncomfortable, and to run, not walk, toward it. So, I shook off the “imposter syndrome” voice in my head and looked back at career moments that made me feel the most energized. They were the ones in which I guided a company through moments of crisis, overcoming my own occasional doubts and reservations, realizing I’d made a small improvement in my journey toward inspirational leadership or helped others make progress.

Rather than being set back by thoughts of failure—whether my own or the company’s—I considered all the incredible opportunities that an exciting startup like AutoGravity would provide me. Sure, things may not turn out ideally, or in a way that I might expect. But, along the way, I would have gained invaluable experience, greater resiliency, and maybe thicker skin. And, I would never have to look back at my career and say, “If only…”