Deciding Whether to Leave Google/Apple/Facebook? Here’s the One Question to Ask Yourself.

Having spent 9+ years at Google/YouTube before leaving to raise our Homebrew seed fund, I know a little bit about ‘golden handcuffs.’ And the truth is, if you’re a high performer focused on maximizing wealth, you’d be unlikely to ever quit Google, Facebook, Apple, etc (unless you want to roll the dice and found a company. side note: if you do, pls email me). Even if you prize intellectual challenge in addition to your handsome paycheck, these companies (decide if you want to add Twitter, Amazon, etc to the mix) will always have a new opportunity for you which magically appears just as you’re about to quit. “Oh, before you accept that job at Square, how’d you like to work on Google X?” I see this happen all the time – a valued employee prepares to leave and a very attractive comp bump and/or new role makes it easy for them to stay.

BUT WAIT, there’s one question to ask yourself periodically, especially when considering a new assignment over an external opportunity, and that question is:

Imagine you were at a different job you loved and a recruiter from [Google/Apple/Facebook] called you to offer you your current job at [Google/Apple/Facebook], would you chase it? Or in other words, would you re-apply today for the job you currently have?

It’s a rather simplistic question but one which I believe gets to the heart of whether you’re just comfortable, well-compensated, doing something familiar or really pursuing something personally meaningful. The reality is, there’s nothing wrong with not leaving, just don’t play this game with yourself or other companies about “ooh maybe I want to leave, maybe I don’t.”

But if you do answer “no, I wouldn’t fight hard for the job I have” then you owe it to yourself to find something that you can be excited about. This was one of the fundamental questions I asked myself when leaving Google/YouTube. There were several other really compelling opportunities being presented to me within the company and that vesting schedule was nice, but it would have meant professional cardiac arrest. No heartbeat. Not passionate. And I needed to create something that got me pumping 200 bpm.