Note: This is the question. Check out the answer.
Failure sucks.
It’s frustrating, often gut-wrenching, potentially embarrassing and always disappointing.
If you’re alive, you’ve probably failed.
You probably didn’t like it.
It probably seemed like a pretty shitty experience at the time.
You probably felt like a loser.
Welcome to the club.
You’ve no doubt heard well intentioned rhetoric about failure as a stepping stone. Sadly, it’s become a cheap cliché. Easy to pay lip service to, but much harder to actually live when it means being scared or humbled all over again.
Admitting failure can be tough too. It’s scary to lay it all out, plain as day, how much and how often you’ve fallen short. How thoroughly inept or inadequate you’ve felt. Intellectually we know (or are told) it’s part of a process, but it can still land a pretty devastating blow on your self esteem.
Of course the devastation is self-inflicted. In order to judge ourselves inadequate we’ve first got to have some preconceived notion of what adequacy looks like. It’s the preconceptions which are faulty not our capabilities. It’s the expectations we should question, not our innate worthiness as human beings.
I know the preconceptions are faulty because it turns out there’s actually a very strong correlation between suckage and awesomeness. I was genuinely awed, and even comforted this week to learn how much failure Derek Sivers had weathered in a single year. Is it any coincidence that his successes are equally epic?
Makes sense. Anything worth doing means stretching well beyond your present capability, and that means—for a time at least—you’re going to suck at it. That’s okay. And it has to be, because it’s pretty much a law of the universe.
Earlier Emilie asked me to contribute a story to her compilation of spectacular, life-shattering failures. And, ironically, I kind of failed at it. I contributed some abstract, general thoughts on failure while cleverly avoiding telling a personal story. Thought I’d rectify that.
So, here’s my glorious (if somewhat abridged) history of humiliating failures. Don’t judge em, celebrate em.












