I hate making mistakes. I always have. All my life I’ve worked to have the right answer, to be safe, to work in the space that I knew I could be good and right and effective.
Until I decided to start a start-up.
Now I’m making mistakes left and right. Because I don’t know what I’m doing. Every day I’m figuring it out anew. Our whole team is.
But I’ve also learned that there are 2 types of mistakes: 1) the strategic kind and 2) the dumb kind.
Strategic mistakes are part of the job.
If you’re not making these mistakes, you’re not pushing hard enough, not trying new things.
Emmett Shear from Twitch spoke at one of our YC dinners and he put it best when he said:
“You don’t know where the line is until you’ve pushed past it.”
That really resonated with me because what is a start-up if not a constant exploration of boundaries? Of seeing what’s possible.
Playing it safe is a certain recipe for death in this line of work.
So we work to test and try. And there will be mistakes. But the key here is to make sure they’re not devastating and irrevocable. That they’re the two way doors, as Amazon puts it.
These mistakes I have to lean into and get comfortable with. They’re the key to our success.
Dumb mistakes haunt me.
I hate these ones. The ones that in retrospect seem so obvious. The ones that you can’t stop thinking about because they were so simple but still you messed up royally.
And it’s usually because I was moving too fast and just didn’t take the extra 5 seconds to think it through. We’re doing so many things on so many fronts that it’s impossible to fully work out the implications of every action until I hit send or I get an angry email or worse, a hurt one.
These ones hit me the hardest. Because I can’t chalk them up to experimenting or testing or trying. This is just me not being diligent enough. This is me failing me. Because I know I’m better than that.
It’s not the action, it’s the reaction that matters.
While both of these types of mistakes are vastly different, they have one thing in common — how to react to them.
We’re human so there is always the instinct to “feel bad”, feel remorse, embarrassment and more.
But we need to feel resolve.
To quickly fix it, to never make that mistake again, to learn, to be better the next time.
We need to channel all of those feelings not in a passive feeling of regret, but an active feeling of anger. Because you know you’re better than that and tomorrow you will be.
So make the mistakes. We all know we will. But then don’t feel bad. Get mad.
Then fix them.