My Life Is 90% Failure, and I'm NOT Cool With That

6.17.15

From the outside, my life looks like a picnic at a theme park on a mid-70-degree day, sometimes with free beer. This is due to a few reasons.

1) My life is actually pretty good.
2) I don't like drama.
3) I've learned to live with massive, heart-wrenching, gut-punching failure.

Look, everything you ever read about entrepreneurship and success starts and ends with failure. It's necessary. It's part of the process. Fall nine times and get up 10. You'll never be anything unless you've failed more than you've succeeded.

But I'm not talking about that easily-digestible, hypothetical, well-we-gave-it-a-whirl failure. I'm not talking about someone giving you a lot of money and it didn't go the way everyone wanted failure. I'm not even talking do all this work and have it perform miserably failure.

I'm talking about wanting something really, really important, really, really bad, and making huge personal and professional sacrifices at your own expense and at the expense of people you care about to inch and claw and struggle and scratch to get so close that you've already started celebrating (even though you know better) and then crazy, coincidental circumstances conspire to snatch it away.

This happens to me. A lot.

It's the worst kind of pain. It's the loved-and-lost pain, and don't believe those rainbow-chasers, it's definitely much easier to have never loved at all. It's failure like Russell Wilson in the last few seconds of Superbowl 49 without all the endorsement money and getting to be a professional quarterback again in six months.

But I've learned to live with it. Because you have to.

What's more is I don't have a secret cure for it. It happened to me again very recently, when something I wanted for one of my kids was right there, I knew exactly what I had to do to make it happen, I did precisely what I thought I needed to do, and it failed. Hard.

And worse, I got a dozen or so reminders over the next week of how awesome it would have been. Every new bit of information came up on the most painful option possible.

I'M STILL GETTING MAD THINKING ABOUT IT NOW.

Sometimes I wonder if I'm being tested. Other times I just write it off as intervention — like if I landed X it would have required me to go to Y and I would have gotten hit by a car or something. But in all cases, I let it go and move on, because there is no other option.

Well, revenge is pretty good.

The worst is when it happens live, when the news doesn't come via email or voicemail, but face-to-face, and you have to sit there and smile and pretend like your guts aren't squirming while you figure out what to think about so that your face doesn't get too red.

Sound familiar?

But yeah, this is something you have to go through. My character is one of those gym rats with the enormous pecs and steroid-looking biceps. It's done so many push-ups and sit-ups and chin-ups that it's strong enough now to withstand almost anything.

That doesn't make it easier, it just means I'll keep getting up.




Let me know what you thought about this article, good or bad.

Your Email Address

Leave it blank to be anonymous



Your Thoughts?





Here's Everything You Should Know About Startup
Over the course of 20 years and 10 startups, I've built up enough stories and scenarios to be able to talk definitively about startup.

Automating Digital Video
Automation can use the unstructured data produced by video to quickly and efficiently tell us what's in that video.

Chasing Money, Trading On Your Name
So this is the last episode with NFL Quarterback, entrepreneur, and all-around great dude Thad Lewis.

Athletes and Entrepreneurs, Confidence is Everything
The Teaching Startup crew definitely got rolling with this episode and it produced some of our most entertaining and interesting content.

10 Minutes on NPR to Understand Automated News
So I gave a radio interview to NPR last week on the future of news and automated journalism.