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Why You Should Fail More This Year

Failure is horrifying. It is literally defined as the inability to get what you want, or to get what you don’t want.

So why do I think you should try to fail more this year?

Because failures are crucial to meaningful achievement and self-discovery. And when you can see them this way, failures won’t feel like disaster, they’ll be challenges that help you bring your best to the table. Let me explain.

Failures have two great qualities:

1. Failure Will Teach You Your Limits

You could not learn as much about yourself from a laundry list of successes as you would from one well-timed, well-analyzed failure.

You’ll learn more about your alcohol tolerance from one blackout than a lifetime of moderate drinking.

You’ll learn more about the limits of your emotional tolerance from one broken relationship than dozens of “safe” friendships.

You’ll learn more about what drives you from one burnout than decades spent avoiding over-commitment. 

Failure is a crucial educational tool. In any aspect of your life, until you fail, you can never be certain where your boundaries are. And if you don’t know where your boundaries are, then you can’t push when you can, and pause when you must.

Of course, this comes with a rider. Fail safely. Jumping without a parachute isn’t the way to learn the limits of your improvisation skills, taking an improvisation class is. Failure as an educational tool only works when you fail in ways that you can learn without causing long-term damage to yourself. Use your discretion. Don’t blackout.

2. The Peak is Only as Enjoyable as the Climb is Difficult

But I’m not just advocating failure to you just because it is educational. I’m advocating failure because the possibility of failure makes the eventual achievement meaningful.

For any pursuit in life, if there was no possibility that you might have failed then you didn’t aim high enough. You sat out the adventure.

In fact, there is a well-documented psychological idea called effort justification that backs this. The idea is that people tend to value an eventual outcome more if they had to struggle to get it. 

But we don’t need  a psych study to accept the point. Its obvious that the goals that are really worth pursuing are the ones that make you stretch. And this means there’s a chance you won’t succeed. But now you know: this possibility of failure is necessary for the eventual achievement to be worth it.

So that’s why should fail. But, what about how  you should fail?

How to Fail Right

First, here are the kinds of failures you should be seeking:

If you’ve always wanted to be a writer it’s time to fail at it. Set yourself a specific goal that will actually get you writing; one you could possibly fail. Say, “Write 15 articles in the next six months”. Challenge yourself to write all 15 regardless of the reception you get. You’ll find out exactly how much you care about writing, how hard it is to actually write, and whether you’re ready to put more time into the pursuit.

If you’ve wanted to meet more people, set another goal; start reaching out. Reach out to two new people every week—from work, the park, or anywhere else—and invite them to share a meal. Whether or not you manage to go through with it, you’ll about yourself, about the kind of relationships you want to have and those you’d rather live without.

If you’ve considered being a comic, do an open-mic (or five). Make sure you show up. Most of your jokes are going to bomb. You’ll realize that other comics bomb a lot too. All comics bomb from time to time. The experience will teach you more about your passion to do comedy (and how comedy actually works) than any number of funny dinner-stories you’ve told close friends or times you’ve spent fantasizing about a comedy career.

You can set these kinds of goals for any aspiration in your life: to exercise more, complete a creative project or anything else. The idea is to verbalize your vague aspiration into something specific and achievable in a particular time-frame. Something you can fail quickly.

This is an activity you’re going to resist because it’s much easier to let your dreams fizzle out slowly than to actually take the leap and see how far you land. But the moment you set this goal and open yourself up for failure, you do two things:

First, you set yourself up for the possibility of success. Second, by simply starting, you guaranteed yourself dramatic learning. Even if you fail, whatever causes your failure will teach you something more about yourself and your goal.

Of course, truly failing well requires that you then pursue these goals with due diligence, and eventually, it requires you to reflect deeply on why you failed or succeeded. But it all starts when you set an intention and embrace the possibility of failure. And that’s something you can do right this moment. 

The Main Point

I guess what I’m really saying here is that there are two kind of failures. There’s failure in the narrow sense, which is the failure to get a specific result. Then there’s failure in the broad sense, which is the sense that your life as a whole is a failure. 

All I’m saying is that to live a full, rich and successful life in the broad sense, you have to welcome failure in the narrow sense.

And seeking narrow failures in this way is the opposite of seeing your life as a whole as failure. Narrow failures should not come with disappointment in the same way that narrow achievements do not come with lasting satisfaction. Satisfaction is something you live in now, not something you can achieve later. So being satisfied and grateful is a skill you must practice in your present regardless of whether you accomplish your goals or not.

But goals still have an important place in your life. Because life is change. So even if you’re satisfied with your present in general, you can’t be static. You’re not exempt from the movement of life.

Goals just help you move with purpose rather than by accident.

And to move with purpose you aim directly at the things you want. Which, I’ll warn you, is going to be scary because if you try, you might fail.

But because you might fail, you know that your endeavors will be worth it.