How to Fail Well

This is what I feel like when I fail — but not everyone sees it the same way. (Photo: paymycollegedebt/

Recently, I failed. Not in a way that others could see; it was at something that probably nobody else noticed. It was, to put it succinctly, a personal failure. That is, one that made me feel like I had failed a self-defined goal. For me, those are the worst kind of fumbles — when I have disappointed myself it's much worse than anything else. (This may be a basic personality trait, I've been this way for as long as I can remember; I was always much harder on myself than my grandmother, who raised me, could ever be.) The goals that other people — society at large — set have never moved me because those that I set for myself are intangible and incredibly lofty. Too high, too weird, too out-there maybe, but they are mine.

What I've realized while I've been nursing my own (self-inflicted) wounds is that it doesn't matter how you fail — whether you are a self-directed, introverted only child like I am, or a courageous, extroverted individual who thrives on community. When you fail at something, it feels absolutely terrible. Gut-wrenching, nauseating and resulting in a reach-for-the-vodka mentality that makes you wake up with a headache and a just-deferred heartbreak. We see so many examples of triumph, of winning, but precious few of failing — but the two go hand-in-hand, right?

So I've been doing some reading and apparently, there's a way to "fail well;" people like Steve Jobs and Einstein and Beethoven did it. Sir James Dyson practically prosthelytizes about it: "The most important thing you need when redesigning something is perseverance and a willingness to fail ... Failure is the best medicine — as long as you learn something." So now I need to figure out how to take this uncomfortable feeling and make it work for me. Failing well entails using your defeats as stepping stones to your triumphs.

It is a newish concept that goes against what many of us have been taught over the years — that it's not only OK to mess up, but it's a good thing. In this way of thinking failure means you are pushing your limits, going outside your comfort zone, and doing that which you feel that you are ill-prepared for. And so, when you crash and burn after pushing your limits, you must pick yourself up again and keep going, having gained from what you have lost.

But how?

Because Steve Jobs failed so much — and ultimately became so successful — he is the current go-to guy with respect to "failing well." In this article, Jobs's old friend, Nolan Bushnell, reveals how he did it so well. "While leading Apple, Jobs learned a thing or two about failure. In the early 1980s, dismal sales of the Apple III and its follow-up — a computer Jobs pushed for called LISA — caused Apple to lose nearly half its market to rival IBM. Sometimes the market, the people [and] the idea aren't right but you have to move on, [and] try again," Bushnell says. "If you lose a game of chess, you still set up the game and go at it again." And if Steve Jobs can do it, so can you.

Another famous failer was Edison, who famously performed 9,000 experiments before figuring out the light bulb. Then there's Stephen King, who details the number of rejections he received in his memoir, "On Writing" before his first, second and third short stories were published. J.K. Rowling was another writer who hit "rock bottom" and used that energy: “Failure meant a stripping away of the inessential. I stopped pretending to myself that I was anything other than I was and began diverting all my energy into finishing the only work that mattered to me.”

Failing is now a technique that's commonly taught in business schools: "Students of entrepreneurship talk about the J-curve of returns: the failures come early and often and the successes take time. America has proved to be more entrepreneurial than Europe in large part because it has embraced a culture of “failing forward” as a common tech-industry phrase puts it: "In Germany, bankruptcy can end your business career whereas in Silicon Valley, it is almost a badge of honour."

Teaching kids how to fail is now an actual thing, and there's even a blog called The Art of Failing Well: This blogger's advice about failure is a bit dark, but useful; if you look at how many days you have left to live (he has a death clock), you will be continually motivated to pick yourself up after you fail. "for me, the death clock is a tangible link to the first step of failing well. Knowing that your time is limited and to deciding how to spend it."

Seeing all the examples and quotes out there about failure has heartened me, and also made my own situation seem less fraught. It's also helped me genuinely shrug my shoulders and say "I failed. So what?" knowing that there are legions of smart, talented people (including some of the smartest and most talented in the world) who messed up and moved on. Being in such good company really is a buoy to negative feelings.

And being OK with failing means I'm more likely to take a risk next time — and those actions make it more likely that I'll succeed in the long run.