Failing Up? 7 Practical Ways To Make Failing Your Friend

Not to brag, but I’m kind of an expert at failing.

I know, I know, these days everyone’s an expert. But, for real, I know a lot about failing. And not because I made it the focus of years of academic study — though I’m sure many a dissertation has been written about failing, and I did spend rather more than my fair share of years in higher education.

Instead, I’m an expert on failing because I’ve failed, a lot. You’re probably thinking “Well, then I’m an expert at failing, too, Clare, I missed my train this morning and spilled coffee on my new tie.” However, not only do I fail a lot, I actually used to teach people how to do it.

In a former life as part of my graduate studies at the University of Montana, I taught Introduction to Acting. And if you had the dubious honor of finding yourself in one of my classes you can probably still hear my voice echoing in your memory, enthusiastically shouting:

“Yay for Failing!”

Yes, this inspirational phrase was a key motto of my classes. It’s sort of a simpler version of what Samuel Beckett (arguably the greatest playwright of the 20th century) said:


Used with permission, Artist: Arturo Espinosa, changes were made

What I was constantly challenging my students (and myself) to do, was to make failing our friend, to celebrate failing, and to fail better.

Nothing innovative, creative, or original can be made without a willingness to fail on the part of the person attempting the creation. If you are going to improve, you have to try something new, and trying something new means you might (heck, probably will) fail.

Back in my teaching days I had a whole semester to teach my kickass students how to embrace and celebrate failing, but I’ve probably only got you for another few minutes, if I’ve been lucky enough to keep your attention with my pithy prose up to this point (and if not, ‘Yay for failing’, right?!).

I’ve broken it down into seven practical steps.

Step 1: Understand What Failing Is

If we want to get super basic with it, let’s check out what the dictionary has to say on the matter.

Here are a few ways Merriam-Webster defines the word ‘fail’:

  • To fall short
  • To be or become absent or inadequate
  • To be unsuccessful
  • To disappoint the expectations or trust of
  • To miss performing an expected service or function for
  • To be deficient in
  • To leave undone

But what else is failing?

Failing is human. It’s an essential part of the human experience. So much so that philosopher St. Augustine asserted fallor ergo sum. Translation:

I err, therefore I am.

This 4th century theologian was onto something. Trying and failing are part of the shared human experience.

Failing is also subjective. Can you remember a time when you thought you had really messed something up only to find out you were #winning ? This happens to artists all the time. They write a song, choreograph a dance, paint a picture and think, “Dang, this is the worst thing I’ve ever done, this is garbage.” And then someone else sees/hears/experiences it and thinks, “Dang, this is the best thing I’ve ever heard/seen/experienced.” Of course, there are times when failing is less subjective, the meeting started at 4 and I arrived at 4:30, the ceramic mug I made doesn’t hold water, etc. But oftentimes we view our failings as much more absolute and detrimental than they seem to others.

Perfection is an illusion. It is often our perception that anything short of perfect is a failure that leads us to weight our failings more strongly than someone else might.

Step 2: Understanding What Failing Isn’t

This one is really important, and was often the crux of what I taught my students about failing. Failing isn’t not trying. Can I say this one again for the cheap seats in the back?

Failing isn’t not trying.

Turns out, when you tell a bunch of college freshman that you celebrate their failing, this gives some of them the idea that they can just show up to class unprepared. Yay for failing, right?

Nope. Here’s an important distinction: Failing to try is not the same as failing.

One of our assignments in Intro to Acting was to learn how to juggle. Confession: I am a terrible juggler, and would only practice when this time of the semester came ‘round again. When the day came for everyone to get up in front of the class, one by one, and try to get ten successful catches of their juggle-able objects, without fail, every semester someone would walk up in front of the class and petulantly throw their balled-up socks in the air and let them fall to the ground. Yay for failing?

No! F for not trying.

Everyone’s favorite muggle, J.K. Rowling once said, “It is impossible to live without failing at something, unless you live so cautiously that you might as well not have lived at all, in which case, you fail by default.” So yes, throwing the socks up in the air was a fail, of sorts, but it wasn’t constructive failing. And this is a distinction I want to make here. If you haven’t actually put in an effort, risked anything, or tried, then you haven’t really failed. Constructive failing happens when you really put in an effort, take a risk, and learn something from the outcome of your swing and miss.

Another important distinction needs to be made before we move on to Step Three.

Failing doesn’t mean you’re a failure.

Failing just means you failed. It’s a simple as that. You tried, you failed. Be like Beckett: fail again, fail better.

Step 3. Increase Your Opportunities to Fail

Failing doesn’t feel great. Actually, it usually feels pretty terrible. But you’ve probably guessed it, if you’re gonna get comfy with failing, you’ve gotta do it more often.

I do have some words of comfort here though: this really does work. I’m not going to lie to you and say I’m completely and totally, make-up off, wearing my sweats, morning-breath comfortable with failing; especially not when it comes to things that are really important to me. But I can confidently state that the more often I fail, the easier it gets to embrace.

Discipline is born from adversity and failure. Resilience is built from hearing no, missing the shot, and not making the cut.

How do we increase our opportunities to fail without triggering a mental breakdown or sending our lives into total chaos? That brings me to Step Four.

Step 4: Fail Small

Try some new things, and get more and more friendly with the feeling of failing.

Remember that juggling I mentioned in Step Two? Grab some tennis balls and take to YouTube!

Borrow Grandma’s knitting needles and drop a stitch or twenty on your way to your first very knobbly scarf. Round up some friends and head to your local ice rink and rent some skates.

Caveat: If you’re an expert juggler, a wiz at knitting, and a professional figure skater, these things do not apply! This is about finding small activities that you may not be great at yet, but where your failing at them is of little consequence.

Ask yourself: What are are a few things that I could try, that it wouldn’t matter if I fail?

Ask out that cute barista? Take a stab at the Sunday NYTimes crossword puzzle? Challenge your mom to a game of Boggle? If you’d like some hilarious inspiration for daily fails check out Jia Jiang’s vlog 100 Days of Rejection.

You can also fail small on your way to proficiency in something. Try out that song at a small open mic. Invest $5 or $10 in a conservative investment. You knew I’d have to bring up investing eventually, right? You are reading this on Stash’s website/app. But my point stands, learning any new skill involves trying a few things out and not beating yourself up when you get it wrong. You sing the song at an open mic and you forget your lyrics. So what? It was only your friends and a sassy bartender watching, anyway. You bought an investment and it lost value.  Don’t panic. It’s part of learning how the market works.

Small fails help us get more comfortable with failing. However, this isn’t to say you should never fail big.

Step 5: Fail Big

I know, the fail small section was a lot more fun. Skating, knitting, crossword puzzles…and apparently very nostalgic, too.

But now we are on to Step 5, and if you are really gonna make failing your best bud, or even a solid acquaintance, you’re gonna need to take a few risks.

A former director and teacher of mine in London had a fantastic shirt that simply read:

Risk and You Shall Receive

Sometimes you need to take the risk, because without it, you will rarely receive the reward. After all, if you don’t ask the question, the answer is almost always ‘no’ by default. Sometimes we need to take that risk. Ask him to marry you. Request the raise you deserve. Register for that crazy marathon obstacle course that intimidates the crap out of you.* And you know what, he might say no. And you might not make it through the race. But sometimes you need to take the risk. Your comfy factor with failing needs to be put to a real test occasionally, and it might hurt, but you’ll (probably) survive.

* Important note: The author is not liable for any failed proposals, salary stagnations, or obstacle course bruises, but is more than happy to celebrate those failings with you in spirit!

Step 6: Celebrate Small Wins

You probably have more wins in your day than you realize. Just moved to a new city and got on the right train or off at the right exit on the 405? Small wins! Spending spring break in another country and successfully remembered which coin is worth the amount you needed? Small win! Increased your Auto-Stash from $5 to $10 a week? Small win!

Recommended reading: The Simple Money Challenge You Should Start Right Now 

Let’s get personal for a moment.

Another reason embracing failing is so key to my life is that I am a Type 1 Diabetic. This means that I try, and continually fail, to keep my blood sugar at an optimal level. However, sometimes I get it right! And when I do, I try to celebrate those moments. Just not with a donut.

With such a small margin of error, it can be really hard not to beat myself up when I fail and get it wrong, which is almost every day. So I’ve learned that it is incredibly important to celebrate the moments when I get it right. This doesn’t mean I throw a party every time my blood sugar is in ideal range (though that sounds kinda fun, and I might consider that); usually it is as simple as pausing for a moment and giving myself some credit.

This strategy can be particularly useful when you feel like you are drowning in fails and the “Yay for Failing!” mentality isn’t really doing its trick anymore. Take a moment, breathe, and think about what small wins have happened in your day, or week, or year.

Celebrating these small moments can also be a key to forgiving yourself for the perceived failings you weren’t able to embrace.

Step 7: Know You’re in Good Company

Finally, know you aren’t alone. Failing is part of being human. It can be inspiring to read about the failings that came before the successes of some of our favorite people. We’ve all heard about Edison’s assertions about all the ways he found not to make a lightbulb,  Harrison Ford’s years as a carpenter, and Michael Jordan being cut from his high school basketball team. Research these failings. How did some of your idols fail? How do they continue to fail?

It can also help to share your failings with those close to you. Vulnerability can be powerful, and can inspire others to share their fears and failings as well. We often try to hide or minimize our failings, while experiencing them incredibly deeply ourselves.

A few of us also feel we need permission to fail. I know I have experienced this throughout my life. Not all of us work at X (Google’s ‘semi-secret research and development facility) where Astro Teller, their “Captain of Moonshots” asserts that failed projects are actually monetarily rewarded. (Check out more about this in his TED Talk found in the link below). And not all of you were lucky enough to find yourself in my classroom shouting “Yay for Failing” every Tuesday and Thursday for a semester.

If you’ve ever felt you needed encouragement, or even permission, to fail, here you go:

As an expert at failing, I give you permission to fail. Use it often, and well.

I’m not the only one who is a super-fan of failing. Turns out there are lots of super smart people who have given TED Talks on the subject. 

Check out: 8 TED Talks that Help Us Embrace The Epic Fail 

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