When I was 19 years old I dropped out of college. I had no savings. The most I’d ever earned was $14 an hour from a programming internship at a startup, Stamps.com, the summer before. I felt horrible about it at the time, and so one day I decided I would solve the problem. I called my parents up, and told them I was going to quit college. I explained: So that October, making less than $10 an hour and still living in the dorms, I decided to quit The University of Michigan. I soon found a job with a startup, Xtime, in California. They were looking for a junior engineer to help build and run cloud infrastructure — it was perfect. I might have taken the job for free, to learn, as an intern. They offered close to $80,000 full-time. I accepted on the spot. During the height of the dot com boom I moved out to Silicon Valley — and at 19 years old experienced two years of startup highs and lows. I was living the dream, learning new skills faster than ever, and packing away knowledge that’d be invaluable down the road. When I was 26 I started my first startup. I’d been at Microsoft just over 2 years, a former classmate and I’d been kicking around ideas for some time and we’d decided to make a go of it. So I quit my job over the summer, and by early the following year. I’d failed miserably. When all was said and done I’d gone 8 months without a salary, spent all the cash I’d put into the business — and we had no customers, no product, no vision we could clearly articulate, and no clear path to getting on-track. To make matters worse, my friend & I had been living and working together in close quarters on a shoestring budget, and by the end we were just barely on speaking terms. I felt angry. I felt ashamed. I was a bit broken. I took some time to recover. So was it worth it? Still in recovery and not yet ready to start from zero on another startup, I wasn’t sure what to do next. I made a commitment to myself not to go backward or stagnate in my career. I wanted a new challenge. I wanted to learn new skills. It led me to a phone call with a former colleague back at Microsoft who’d been looking for help building a team… half way around the world in Shanghai, China. When interviewing for the job, I vividly remember the recruiter asking: “So did you just decide you liked big company life a bit better?” Six weeks later I was on a plane. I spent nearly 3 years in China — learning new skills, growing as a person and a leader, and having amazing life experiences along the way. I’d failed at starting my first startup… but came back stronger and more experienced than ever before. Earlier this year I started a new adventure at Google. What happened last year with the recent startup? In short, after the better part of a year working to get a second startup off the ground, I began to realize how deeply I enjoy creating new products and new technology — moreso than so many other challenging aspects of keeping a new business afloat. Where in past roles I’d spent nearly 100% of my hours creating and designing new products or leading teams doing the same, in my new role the time split was rapidly evolving away from this — and quite unexpectedly I wasn’t finding nearly as much joy, meaning, or satisfaction as I originally imagined. My co-founders, of whom I can’t speak highly enough, were similarly facing struggles, and together we agreed weren’t positive enough on the journey thus far to want to embark on the next 3–5 years — a period of asking investors for funding and recruiting team members to follow us. It was an incredibly difficult decision, but one I’m glad we made early on. Out of this whole experience came a realization — of how fortunate I am and so many of us are to work in an industry that’s thriving, how many opportunities there are out there to find joy in one’s trade. At Google, I’ve been able to return to my Product core, working in a space that’s new and exciting, rapidly evolving, and creating a steep learning curve and fun challenge. As 2015 came to an end, I found myself thinking back on my career to the many points where I might’ve taken the “safe”, linear path — avoiding fear or chance of failure. I wonder where I’d be, or wouldn’t be, today — what experiences or opportunities I might’ve missed, what regrets I might have had. These days, when people still early in their careers reach out for advice, there are 3 quick reads I often share:
It was the start of my sophomore year at the University of Michigan, and like the year before I was skipping class, wasting away my parents’ hard earned savings on expensive out-of-state tuition.
A crash course in failure
I answered honestly: “I tried something and it didn’t work out. But I’m looking forward to the challenge ahead.”
2015 — Meaningful work, re-visited
Home Success Stories Case Studies - Successful People From a college drop-out, to working at Google: A story of my...
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