How to Quit Your High Paying Job

In 2011, I left the highest paying job I've ever had. It was so much money that I'm still ashamed to tell my parents what I left on the table.To set the stage, I was leading frontend engineering AdMob and Google acquired us. We were a pure mobile ad company that mobilized AdWords and AdSense. My job was to incorporate our mobile functionality with their multi-billion dollar run rate products. It was not an easy task to convince teams responsible for Google's cash cow that mobile was different and they needed more than an "is mobile" checkbox.My days were spent persuading teams that this mobile thing would be big someday. I had to prove that if AdWords added mobile targeting it would result in higher quality clicks. At the time, mobile was still a fraction of their traffic. On top of that, innovation on AdMob's platform was also at a standstill because the plan was to sunset.As the year wore on, there would be days where I felt we were running up a hill, an icy one... on roller skates... pushing a 500lb boulder.Days would pass where I would go home feeling I had done nothing productive. Mornings where I laid in bed thinking it would make no difference if I showed up that day.But I had the "golden handcuffs." I had to go to work. It was simply too much money to give up. What if I never have this chance again? I would be an idiot if I left. What would my parents say? Am I crazy?My decision to leave began because I didn't feel productive. I was unhappy because my efforts barely moved the needle. But the money! How could I give up all that money?So, I made a spreadsheet with my vesting schedule (including several projections for Google's stock price). I looked at the years to come; 2012, 2013, 2014, etc. I imagined one more year of pushing that boulder uphill and then at the column that represented my future bank balance.Was that number worth it? Was it worth another year of feeling unproductive? Was I learning and expanding my skills? What opportunities am I passing up if I only stayed for the money?The decision was easy at that point and the answer was a resounding NO!All my fears stemmed from losing the easy money. I was afraid I'd look like a fool for giving up the unvested shares. I realized more money wasn't going to make me happy. So I left.Looking back 3 years later, I couldn't be happier with my decision. I've learned and developed skills that I would have never developed at Google. I've prototyped products, founded a company, built a team, joined LinkedIn, and never looked back.