How I navigated my biggest career transition

One year after exiting my role as Google’s Chief Decision Scientist

Exactly one year ago today, I left my position as Google’s Chief Decision Scientist to venture out into the Great Unknown on my own. (Here’s the blog post I wrote about it last year.)

Since we love simple narratives, most people won’t tell you the truth about their leaps. You only get the tweet-length scrubbed down version that’s all squeaky clean with hindsight bias and survivorship bias.

• Hindsight bias: the “I knew it all along” effect. Hindsight is 20/20.
• Survivorship bias: you’ll learn the wrong lessons when the loudest voices are the success stories and you rarely hear from the failures.

So, here’s an attempt at a more truthful update.

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First of all, did I have a plan as I was leaving Google? Absolutely! Are you kidding? Of course I had a plan. I had plans within plans. I’d been planning my exit for over a year.

Is having a plan the same as knowing where you’re going? Not always.

Is having a plan the same as knowing where you’re going? Not always. And certainly not in my case.

Having watched close friends exit high-powered corporate positions, I’d noticed some patterns and bits of advice that I’ll share with you here since they turned out to be spot on in my case.

#1—Start preparing well in advance

I started preparing for my exit more a year before I actually left. Depending on how you keep score, you might even say it was closer to two years. I’m no advocate of the abrupt exit. Don’t let yourself hit a wall and collapse meekly out of whatever role you’re in. Instead, start preparing your next move well in advance of needing to make it. There’s no disloyalty in planning your future. I’m especially not a fan of the rage-quit-with-no-plan exit style. Do yourself a favor and allow your mind to hold multiple possibilities.

Allow your mind to hold multiple possibilities.