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“This is how you innovate; you fail your way to an answer.”  — Ainissa Ramirez

You’ll learn more from your screw-ups than your successes.

I heard that sentence echoed by coaches, parents and professors my whole life, but only kind-of believed it until failure finally found me.

I’ve screwed up, over and over, in grand fashion, and I’m not done yet.


These aren’t little screw-ups we’re talking about either, like losing a game.

Here’s a snapshot of my hottest fail streak. During a one-month span during senior year of college I was first fired from an internship I wasn’t even paid for, then canned from the waiter job I was barely paid for because I went home to fix my car, which broke down because I didn’t take care of it. A week later I caused a house fire trying to barbecue a steak on a windy day . These events all occurred in the wake of my student organization, a very large fraternity I was president of, being kicked off campus by the Vice Chancellor of Student Affairs only months after I spent more than a year failing to lead its members.

But let me ask you something.

Do you want to be on the table when your surgeon deals with an emergency for the first time?

Do you want to be a stockholder when a company gets their first taste of losing money?

Or even on a sappy personal level, do you want to be the first one to break someone’s heart?

Systematically avoiding failure is far more toxic than failing itself. There’s an extremely vital lesson learned in losing that we tend to chronically avoid out of fear. And the prices we pay — infinite boredom and feeling stuck, just to name a few — are a silent plague.

Ever feel like something’s missing, but you can’t quite put your finger on it? You got your bills paid, a good dog, a decent job and food in the fridge, but something’s just off?

Go fail at something.

Failure isn’t just the ugly stepchild of success, it’s the beating heart that gives it a chance.

Nobody feels failure more explicitly than investors who fund startup companies. And their experience in predicting which crops will rot and which will ripen rebounds my message above.

Writer, developer and entrepreneur Paul Graham said the best metric he’s found to predict a start-up’s success is looking at whether or not their founder has failed at an attempt before. If a startup founder has only succeeded, then it’s far more likely they’ll fail here. But if they’ve failed admirably, their chances at success grow exponentially because they’ll have a clue what to do when they feel things start to slip.

But you’re probably not a venture capitalist or surgeon, so here’s how I think this concept applies to you and me.

Roll the dice. Buy the domain name. Write a ranty blog that nobody reads (hi!). Ask her out. Join the startup. Coach a little league team. By all means, get out of your cubicle and do something you care about. Follow an idea out of passion instead of ration.

Because the only thing that hurts more than losing is being on the bench when time runs out.


I practice permission marketing, the subtle art of never sending annoying bullshit. This way we can stick to the art.
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Reflecting on Robert McKee’s ‘Story’ Seminar.

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