Image for post
Image for post

2. Why I let myself risk failure

When you hear stories about people who’ve done great things, these stories have a tendency to involve a lot of attempts that didn’t make it, and of people thinking that they’re crazy.

It took the Wright Brothers some time to make an airplane fly 12 seconds in 1903, and they were — to put it mildly — ridiculed quite a bit for even trying such an audacious thing. Until they succeeded, of course. People who succeed have this magical ability to change minds. But before they succeeded, they failed. A lot.

Often, were not in a position where we can risk failure, though. If I send my tax returns to an accountant, I’d rather that she didn’t experiment with a completely new way of doing accountancy that just MIGHT give me more money, but also involved a solid chance of failure. I’d much rather have her do the safe and reliable thing and save me some money.

Take cleaning, as an example

What would we say then? Would we say “Sure! Go ahead. Cleaning robots for our office may sound completely bonkers, but we’ll gladly pay you for six months for the chance of reducing our costs by 70% if they work.” or would we say “Very nice idea. How about no?”

The answer is that of course we would go for the robots. It’s freakin’ cleaning robots after all! But we’d probably also hire a different cleaning person on the side, while enjoying our new life as robot investors. We might even write it on our business cards and joke with our friends that we were now in robotics, but we’d still hire a guy to clean.

The reason is simple. At the end of the day (or week), what we want is somebody who cleans the office. Not somebody who sometimes cleans the office, or who maybe cleans the office, or who cleans them extra-well when the stars are right.

What does this have to do with taking risk?

That’s true. If you work for Google X, which tries to come up with wild solutions for the most wild ideas and rewards failing fast and moving on, then hurray! If you’re going to provide balloon-driven internet (which is one of their projects), then you’re probably going to fail, and if you by hard work and miracles don’t, then you’ve revolutionised something, and that’s awesome.

Sadly, most of us don’t work for Google X, or something similar. Most of us work in jobs where it’s best not to fail too often, or things will get messy. Because like it or not, most of us are hired to do something and do it well and reliably, not to try out wild and exciting new stuff and fail fast.

This is where volunteer work comes in.

First off, it should be said that I’m a huge fan of volunteer work, for a ton of reasons I won’t go into right here. One of these reasons, I will mention, though, since it’s important for the discussion here. Doing volunteer work means that you get to do things nobody in their right mind would let you near as a paid employee. Why? Because the chance of failure is high.

If you’re not getting paid, fewer people will stop you

I also missed deadlines and produced stuff that had to be changed. If I’d been a paid layouter, I would have been kicked out within the first week, but since I was doing it voluntarily (like everyone else involved in the project) there was a quite high tolerance of failure. So I persevered.

A few laters I was part of a bigger larp project, and we wanted to layout several hundred pages of game materials. Naturally, I said that I was up for doing it, since none of the others had any experience at all. This time, I got some tips and tricks from a professional, and the ambitions were much higher. The results were also better, even though there were some really horrible mistakes that I didn’t catch. In the text about the elves, “spirit” (ånd) became “duck” (and) because of a formatting error I didn’t notice.

“Under every stone there lives a duck.”

That wasn’t really what we’d tried to say, though it was funny.

Since then, I’ve layouted and published more than a hundred books, magazines, and other publications, and though I’ve made tons of mistakes along the way, I’ve also become better at it than I was back when I was 17. Sometimes I even get paid to do layout, because I’m now at the level where I can provide solid, reliable quality work with a low risk of failure.

But what does this have to do with risking failure?

I used the layout example because it’s a relatively simple one. When doing more complex stuff like events of your own, the risk of failure rises to truly epic proportions. Will people understand what you’re trying to do? Will they want to participate? Will they want to pay? Will something completely outside your control fuck it all up? How will it be remembered?

Running an event of any kind can easily get to a ridiculous stage of complexity, and if you’re trying to do something new/different/challenging, it gets even worse. Of course, creating a new kind of music festival or organising an unusual sort of conference isn’t the same as building the first functioning airplane, but it can feel like you’re up against the same odds.

The amount of people who will tell you that you should do something less risky/crazy/wild/ambitious/etc is huge. Challenging the status quo requires a lot of ice in the stomach, even if it’s for something as relatively harmless as running a meeting differently or throwing a party without alcohol. Yeah, in Denmark where I live, the last one would be a major thing to try in most circles.

The key thing is that if you want to shake things up, there’s a chance you might fail. And that failure can be costly. Especially if you don’t allow yourself to even take the risk of failure. That’s one of the reasons that many people choose to do what they’re good at, instead of trying out things that might just go wrong. Coincidentally, it’s also one of the reasons we (as adults) have a tendency to not want to learn new stuff. We’ll just be bad at it, and no one likes being bad at stuff.

But that willingness to risk failure is critical

For those who want to break new ground, the acceptance of risk and the possibility of failure is a must, though. That’s true in any facet of life, but it’s doubly true when it comes to doing events that challenge the status quo. It doesn’t really matter if you’re doing a golf tournament on a frozen lake, a math class where numbers are forbidden or trying to do communal cooking in a new and interesting way. If it’s new and untested, it might fail.

That’s also where there’s a chance of breaking some new ground.

And even though I’d love to work for Google X, I am more than happy to break some of that new and risky ground doing volunteer projects. Here, I get to fail more (and more spectacularly) and I get to risk failing often. Sure, there’s still a price to be paid when something goes down the drain, but not only is it often not that high (compared to losing one’s job/partner/security/etc), but just getting to take the chance means a lot.

That’s why I let myself risk failure. Not all the time — I’ve got bills to pay as well , and crowds to please—but as often as I can get away with it. And while that has led to a lot of failures, it’s also led to some amazing successes that I wouldn’t be without for anything.

This blog post is a good example. There’s a chance it will completely fail to communicate what I wanted. But there’s a better chance that it will succeed if I try than if I choose not to try at all because it might fail. And if someone had paid for this blog post, they might have fired me if they weren’t satisfied with the outcome. Since I’m doing it voluntarily and on my own time, the worst likely consequence is that people will think it’s a bad blog post.

And that’s a risk of failure I can live with.

Written by

Director, The College of Extraordinary Experiences & Coach at McKinsey

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store