From Dropout to Google and Career Choices In-Between
Eighteen months ago I left a pretty stellar job.
I wrote about it and bared all — my salary, thought process, and story of breaking the news to my boss.
After I hit publish, half a million people read it — and within minutes began leaving comments, reaching out, sharing their own stories with me, and even asking for advice, often on whether to pursue their own change.
There was Aaron, recently out of undergrad and considering an MBA:
“I can relate to a lot of what you’re saying in the post. I feel the same way. I feel lost, uninspired, and that my work is not making a difference in the world. I’m seeking something more meaningful.“
And Molly, thinking about leaving her corporate job:
“I’ve been thinking about leaving my corporate job a lot lately and your article has inspired me. Keep up with doing what you believe in. Thanks for sharing your story. I think a lot of people think about doing what you did but could never go through with it.“
And finally there was Mark, a few years into his career, with an epic question… one that led me to reflect and share so much more of my own journey today:
“I’m 25 years old. I have start-up dreams as well, but my plan is to take your path. Rise through the ranks, save the money, and sail into entrepreneurship waters on a well stocked ship. I’m wondering if you were my age… would you have the same plan?“
The irony is, that was never my plan — nor was it my journey — not quite.
A plan to head West
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.
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.
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.
- They were paying to send me to college because society expected it, not because I wanted, or needed it at the time.
- I had a 2.7 GPA (there went the respectable, big company job!). It was a mix of A’s in classes I’d enjoyed and continued attending — the computer science variety — and D’s in everything else. This couldn’t go on.
- Instead of going to class I was working on a web hosting business I’d started in high school, or working hours at the University’s engineering department. I loved to work. I was learning skills. I was getting paid.
- Quitting wouldn’t be irreversible! I could always decide to make another run at school (and when the dot com economy later crashed, I did just that — gave up my job, went back motivated and with renewed purpose — and that miserable GPA shot up to a 3.8).
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.
A crash course in failure
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?
- Startup failure taught me more than corporate success ever did about my character strengths and weaknesses. It opened my eyes, and might have been the first moment where I truly internalized how and why tenacity, above all else, is critical to entrepreneurship.
- Startup failure gave me a very first taste of the struggle, of what to expect and how to be mindful, of managing through extreme circumstances and emotions.
- Startup failure opened my eyes to the breadth of skills I lacked and set me on a journey to learn them, or meet others who excelled at them.
- Startup failure made me aware of, and tested, my personal values in starting a business. I now feel comfortable speaking openly about them.
- Startup failure taught me that while the goal is success, there is no shame in learning from failure. Nikki Durkin writes beautifully on the subject — and in retrospect I wish I’d failed more gracefully, with more transparency and mindfulness, and more kindness to those around me at the time.
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?”
I answered honestly:
“I tried something and it didn’t work out. But I’m looking forward to the challenge ahead.”
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.
2015 — Meaningful work, re-visited
Google Venice Beach – where my journey continues
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 comes to an end, I find 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:
- The days are long but the decades are short by Sam Altman — so much life+work advice in here worth passing on, some of it non-obvious or often ignored
- Climbing the wrong hill by Chris Dixon — I believe many people can relate, this was certainly me at one point, and to this day describes some of the smartest, most ambitious people I know
- Regret minimization framework via Jeff Bezos — on risk, regret, and principles with which to make good long term career+life decisions
What do you think? What was the most difficult career decision you’ve made? Which path did you take, and what helped you decide?
I’d love to hear your thoughts in the comments. I’ll plan to write and share more as my journey continues.