I Love To Fail

I Love To Fail – Here’s Why You Should, Too.


Featuring five reasons why failure ain’t all that bad, y’all.

I Love To Fail
posted May 21, 2024

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This post is all about why I love to fail – here's why you should, too.

I love to fail. This very blog – arguably my greatest failure to date – serves as very public evidence of that. And although I may not love failure in that immediate FML moment, in general, there's a lot of good to those moments where you fall short.

You see, over the course my thirty-one years and hundreds thousands millions of failures, I've learned a thing or two about the good things that happen when you fail.  Among these "good things", failure forces you to be brutally honest with yourself. Failure is exceptionally humbling. And as you fail more and more, you'll slowly become one resilient motherfucker.

So now, let's break down why I love to fail. And I bet by the time you finish reading this post, you'll want to actively seek out opportunities to fail, too. (Well, maybe.)

This post is all about why I love to fail – here's why you should, too.


1. First and foremost, failure forces you to be brutally honest with yourself.

We're starting off with a real whammy here – and here's the cold, hard truth, friend. You can attribute 99% of your failures to the person you see when you look in the mirror (i.e. you, yourself, and you).

So when – not if – you fail, you might as well just not even waste your energy making excuses or looking for other people to blame. Instead, your energy would be much better spent figuring out what you did wrong so you can avoid doing whatever you did wrong again.

(The only time this doesn't ring true – the 1% – is when you fail at something because of very uncontrollable and unpredictable external factors. For example, if you fail being on time to work because a literal asteroid falls on your car, that one's not on you. That's on the asteroid. You're acquitted of blame in that scenario.)

For example, I've failed (very publicly!) for a year now to generate really any kind of traction whatsoever on this blog. Like, no matter what I do or what I try, I just cannot seem to build a readership. 

And, sure, I could try to blame friends and family for not reading and checking the website religiously enough. Or I could blame Google and Pinterest for "not pushing my content" enough.

But really, it's my fault. Clearly, I'm the one doing something wrong here. Obviously, my content is shit.

And that's called for a lot of brutal honesty with myself as I try to determine WTF went wrong each time. (Mental breakdowns and identity crises, included!) Because as a team of one here, there's literally no one else I can blame for the many flops this blog has produced.

And although I haven't quite figured out the secret sauce yet, I can tell each iteration is bringing me a little bit closer to whatever vision I have.

So the brutal honesty? Pretty effective consequence from my chronic failure.

2. Failure pushes you to explore new routes and opportunities.

When everything is going right, there's no need to reevaluate or adjust course. So you just continue on your merry, little, winning way. Unbothered and undisturbed.

But when you finally fail at whatever you're doing, you suddenly need to find a new way forward – because clearly whatever you were just doing wasn't working. In turn, this failure pushes you to explore new routes and opportunities. Maybe even ones you never considered.

Ones that, you later discover, are actually way better routes than the one you originally envisioned.

This is something I learned when I completely changed careers in my thirties.

Because back in 2014, when I first graduated college and began my teaching career, I never even considered that one day I'd pivot to a career in international tech sales – and yet ten years later, here we are. 

And I have failure to thank for this one. 

Because let's be honest. It's no secret that teachers everywhere earn astronomically shit pay, and everyone knows it. So for that reason, I failed to achieve any kind of financial goals I set for myself while trying to accomplish them on a public educator's salary. This eventually pushed me to explore new routes – and career opportunities – which is how I landed my current role in a whole 'nother industry.

And I'll tell ya what. Salary aside, tech sales is a way better career fit for me, anyway. But it's one I would've never explored had I not failed to achieve my financial goals as a teacher.

3. Failure will turn you into one resilient motherfucker (i.e. failure teaches you how to pull your shit together).

When you fail at something, you realistically have two options. You can either straight-up give up altogether. Or you can pull your shit together and figure it out – and that's exactly where resilience (the ability to pull your shit together after facing a setback) comes from.

And for those of us who fail all the freakin' time, we have learned how to pull our shit together in just about any situation. Even though at first it sometimes feels totally impossible to pull our shit the necessary amount of together.

But somehow, someway, we resilient, chronically-failing motherfuckers always figure our shit out.

For example, over the past few months, I've learned that there's a lot of failure – and a lot of pulling your shit together – involved when it comes dog training.

Because if you don't, and you straight-up give up, what's the alternative? You just have a wild dog?

I don't know about you. But for me... Heck to the no. That was never an option.

Sure, there have been plenty – PLENTY – of moments where I've just wanted to say "fuck it" and let my shit pull apart. But each time I wanted to throw in the towel, I remembered something critical. There was no way in hell I wanted to have a feral dog shitting in the house for the next fifteen years.

So no matter how defeated by the untrained dog I felt at times – no matter how many I thought to myself "I can't fucking do this," as I scooped poop off the floor at 2 AM – I always figured my shit out. And now, we have a dog that won't shit all over everything for the rest of her life.

4. The more you fail, the less scary failure feels.

You know what's scary? The unknown. And if you're someone who doesn't fail frequently, failure probably feels really fuckin' scary.

But for those of us who fail all time, we know failure won't kill us. After all, if past failures didn't kill you, it's quite unlikely that future ones will. It's almost like the more you fail, the more desensitized you become to it.

Take online dating in the Tinder era, for instance. If you want to talk about doomed experiences filled with failure, there's no better topic.

And thanks to that absolutely joyous decade-long experience of mine, I knew more failed relationships (for a lack of better words) than I care to count.  But with every failed fling came another match. And with each new match came a renewed sense of resolve.  

A sense of, Well, the last forty-four failures didn't kill me, so this one probably won't kill me, either, when it inevitably fails. Unless he's a serial killer. (Which was always a very valid concern. Thanks, Netflix crime docs.)

So although those first few failures sucked the most ass possibleit became less scary to put myself out there, fully knowing I'd likely just end up getting ghosted by another internet stranger.

But you know what? After a while, it felt less scary/disheartening and more, "Fuck it. Let's give [insert name here] a go."

Talk about liberating.

5. Finally, failure keeps you from becoming an arrogant jackass.

Or, in more politically-correct words, failure keeps you humble.  Because unless you've got all the unfaltering confidence in the world, it's a little hard to be a little jackass when you're a little busy licking your little wounds, isn't it?

Over my thirty-one years, I've had the absolute pleasure of enduring a whole slew of humbling moments – many of which I touched upon, or at least alluded to, in the previous sections. 

These humbling moments included things like failed job interviews and promotion passovers. Failed entrepreneurial endeavors. Being ghosted and dumped alike by enough fuck boys to populate a small village. Throwing health and fitness to the wind and gaining 50+ pounds over the course of my early- to mid-20s.

The list goes on and on. But I can confirm that each failure was just as humbling and character-building as the last. 

So those are some of the reasons why I love to fail

But now, I'm wondering: How has failure impacted you positively? What about failure do you love? Let me know in the comments below. I'd love to hear from you.

This post was all about why I love to fail – and why you should, too.

John Denn

Your New Internet GBF

On this blog, we chat about all the things related to everyday life in your thirties. From crafting the perfect first Tinder message, to bitching about the price of groceries, to sharing some brutal truths you probably need to hear, we're in this together – and I've got your back, bestie.

John Denn

Your New Internet GBF

On this blog, we chat about all the things related to everyday life in your thirties. From crafting the perfect first Tinder message, to bitching about the price of groceries, to sharing some brutal truths you probably need to hear, we're in this together – and I've got your back, bestie.

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