It’s OK to Make Mistakes

The only real mistakes are the ones from which we learn nothing.

I’m 65 now, so I’ve made plenty of cringeworthy mistakes over the years. I’m fine with that, because in my line of work, making an ass of oneself is an occupational hazard.  

Despite all the times my parents admonished me to: “think before you act,” I’ve learned that for an entrepreneur, the opposite is true. When you are doing something that hasn’t been done before, no amount of thinking is going to tell you how to do it.  You’ve got to try something, see what happens, and learn from it.

The best entrepreneurs think less and do more.  Making mistakes is part of the job.  Whenever I’m asked “what was your biggest mistake?” I’m unable to come up with anything because I no-longer think of my failed experiments as mistakes.  They are just “learning opportunities.”

It’s why I rarely regret making a mistake.  I almost always learn something from it.  And I won’t make that same mistake again.

That said . . . there are some mistakes I do regret.  Usually, it’s when I made a mistake but failed to realize it at the time, and therefore missed the opportunity to learn from it.

But the mistakes I regret most are the ones that may have hurt people.

Let me share two of them:

• At a Netflix retreat in 2000, I jumped in the pool wearing a large temporary tattoo of a “buxom bikini babe” because I thought it would be funny.  I didn’t think much of it at the time, but looking back, I can only imagine how our female employees must have felt seeing this – probably hurt and disappointed. They had just watched a leader at their company wearing something depicting women as sex objects, solely because he thought it was funny. 

• At that same retreat, in a skit satirizing the movie “Bring it On,” another exec and I dressed up as the East Compton cheerleading team in do-rags, oversize jerseys, baggy shorts, and a lot of gold chains. This was cultural appropriation, and racist as well.  

What’s even more appalling is that when I wrote about these incidents in my book – just four years ago – I positioned them as positive, fun stories that I remembered fondly. 

The retreat, I explained, was about culture-building. But that certainly wasn’t the culture I intended to build.  Moments like these don’t just hurt people, they actively work against efforts to build strong, coherent teams.

I do my best to be realistic about who I am.  A large part of that is constantly reminding myself how much of my success I owe to luck.  Not just being in the right place at the right time, but having been born a white male, to affluent parents in a comfortable community.  

But it’s equally important to recognize the other things that shape who you are – especially the traits that can subconsciously undo the good you are trying to do in the world.  I’ve worked to stay humble about my success, but I need to work at identifying my blind spots as well.

Looking back at my behavior – no matter how far in the past it took place – is about more than just apologizing for my missteps.  It’s also about learning to recognize my own biases and continuing to work at overcoming them.  It’s about using what little influence I have in the entrepreneurial community to help others avoid those mistakes.

 But mostly, it’s about remembering that no matter how old we are, we should never stop learning from our mistakes.  Because that’s the only way to avoid making those mistakes again.

Many ideas in this post were first discussed in the Neverland entrepreneurial community. Join us there!

Don’t miss another word. Sign up here to get these posts in your inbox