Willingness to Fail
You can rarely learn from praise. A lesson I wasn’t expecting to taught that morning.
In February 2009, I was a junior software engineer at Amazon. We had just come off another record-breaking holiday season, and the stock price was soaring. At the quarterly all-hands, the anticipation was electric as we waited to hear just how remarkable the numbers were.
Jeff Bezos quietly walked on stage and started with a slide showing the latest cover of Barron’s magazine.
“This magazine actually says Amazon is the best retailer in the world.”
Ah, yes. Time for us to all pat ourselves on the back.
He paused. Then he put up a different slide.
The new slide featured the same publication but 10 years earlier when Barron’s wrote an entire cover story on how Amazon was doomed.
“I wanted to leave this one on while I talk, because this one makes me more comfortable.”
Surely he was going to gloat how wrong this magazine got it 10 yerars ago.
Yet, he continued, instead, addressing the overconfidence we all walked in with.
“When the stock is up 30% don’t feel 30% smarter, because when the stock is 30% down, you’re going to have to feel 30% dumber.”
Wow, a scolding was not what I expected after a record quarter.
Jeff continuied “One of our greatest attributes is a willingness to be misunderstood for long periods of time if we think we are doing the right thing. If you get addicted to the first cover, all the sudden you can’t do that. Willingness to be misunderstood is what allows us to invest and what allows us to fail. You can’t do experiments if you are unwilling to fail.”
The logic is simple: If you are unwilling to fail, you cannot experiment and take risks. And if you cannot experiment, you cannot innovate.
It’s not that you should strive to fail but rather the willingness to fail and take risks is what will allow you to succeed.
This wasn’t performative. He genuinely preferred the article that critcized us. He looked concerned we were going to overfit to the praise coming in.
Jeff added “You can’t learn much from praise. It’s not that useful. It’s often repeating some success or detail you already know. I’m much more comfortable reading critique because there might be something there we can learn from. It doesn’t mean to listen to all criticism. But, in critique, there may be some truth, something there we haven’t considered”
That morning changed how I thought about reception from others. Praise feels nice, but it rarely teaches, it is rarely productive. The real lessons come from critique, discomfort, and feedback since that builds and sharpens your willingness to fail.