You Will Fail. And It’s Okay.
Everyone fucks up sooner or later. It’s not the end of the world.
I know this sounds like the same advice that entrepreneurs, creatives and freelancers hear every day. We’re told that we can’t give up. We can never stop trying. Quitting is for the weak. You only truly fail when you walk away.
But there’s a reason we repeat this advice.
The reality is, every now and then you are going to fail. Because every now and then, you will reach a point of objective failure, where to continue, to keep trying, to just *believe* would feel like a mistake, and it’s at those points that you cannot give in.
There’s a point where you have to accept that the path you have been on, and the product you’ve been building, and the profession that has taken centre stage in your dreams, are not the right fit.
But that’s not the end of the world.
There is no shame in resetting.
I think there’s a real problem with how we view failure. When you’re a multi-billionaire, you’re praised for all the times you missed a shot, fucked up and fell through. It’s admirable.
When you’re not yet at that level, when you’re still going through those failures without a glimmer of success and without a big break, it feels like something to be totally ashamed of.
But admitting you’ve failed when you’ve made a decent, thoughtful, carefully balanced call that you need to try a new idea, a new strategy, a new solution? That’s a good thing. It means you won’t waste any more time on a project that is going nowhere.
Throwing in the towel doesn’t mean you’re a loser, or you’ve given up on anything. It means you’ve reset your priorities and your workload and your dreams, and you are about to get the fuck over it and find a brand new challenge. Or a brand new way to take on the old challenge.
There are some problems that cannot be solved.
You are going to come up against some moments in your life, both professional and personal, where you can’t win. They’re true Kobayashi Maru situations, where no action you can take (beyond cheating…) will lead to a positive outcome.
No matter how much you believe, or how focused you are, or how productive you can be, there are always things that cannot be done. Or that simply cannot be done by you.
When you reach these situations, being able to identify the futility is incredibly important. Because if you can’t do that, you could waste the rest of your life tilting at a windmill and telling everyone it’s a giant. Nobody will be fooled.
It might even be that your product is right, you’re right, but the timing is wrong. The company is wrong. The strategy was wrong. Any of those things could mean that you’ve hit a wall, and you need to burn everything and walk away and come back with something new.
You’ve got to be a big enough person to see through your own reality distortion field.
Iteration isn’t losing.
When we idolise the failures of billionaire founders and successful artists, we tend to only focus on their iterative process. What we call fuck ups were really tests, hypotheses and early versions of future successes.
I think we’ve reached a misunderstanding of what losing is. It’s not missing your target market, making the wrong product or focusing on a bad solution. Those are all learning opportunities, not the end of the road.
Losing is when you have reached a point at which there is no going forward and no going back.
In fact, losing is when there is nothing left that you can do to save your ass. And you have to walk away. That’s not the same thing as failure.
When you fail, and you can’t see a way out, there could be a chance to make some changes and take another shot. You can make a clean break and start again.
Failing is only bad, if it’s the last shot you take.
I almost drowned once. I was surfing on a secluded beach in Sydney, and there were no people around. No surf life savers, no other surfers. It was early in the morning, and I’d headed out to catch some waves before I hit the office.
I was dumped by one particularly large wave, and suddenly everything went wrong. I can remember my leg rope’s velcro breaking, and the rope becoming wrapped around my neck, dragging me under the board.
I couldn’t come up for air, because the board was on top of me, and the leg rope had me frozen with fear. I was starting to choke.
To this day, I still don’t know how I managed to disentangle myself, but I know I passed out and ended up on the beach.
And that was the last time I ever went surfing. I came to, looked at the ocean, and felt so utterly terrified that I never took another shot. I failed once, and I gave it up completely. I couldn’t even skateboard after that.
To me, that’s what losing is. Losing isn’t failure. It’s not having the raw fucking guts to get back on the board and go for it again.
When you fail, when you go through that shitty process, when you’re so incredibly terrified that taking another try with something new feels impossible, you have to do it. Because if you don’t get back in the water then, you might never manage it.
If you enjoyed this article, please click that little green heart below. That would be incredible.
You can also read this. It’s a list of quotes that guide my life. And I believe in all of them.
Thanks for reading — I’m Jon Westenberg. I’m a writer, critic, creative & digital evangelist. Since 2013, I’ve been helping people make things and find an audience. You can ask me to work with you, invite me to speak at your event, or set up a conversation on your podcast. I’m excited to hear from you!