How to Fail Spectacularly, Over and Over Again (& Keep Going)

I am writing 100 How-To essays. It is a big project. Here is why I am doing it. This is essay 15 of 100.

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I have lately done a lot of internet bragging.

Sometimes I feel okay about doing it. Sometimes I’m like, “Well yes, thank you, I do deserve all these accolades and successes, and the reason for my great deservedness has to do with how incredibly I failed at middle school.”

By which I mean: I am RELATIVELY SURE that of all the hated people at my middle school, I was actually the MOST hated. I know, I know: middle school sucked for everyone and everyone had a bad time. My bad time was surely no worse than anyone else’s bad time. 

But here are things that ACTUALLY HAPPENED TO ME in middle school:

- People lined up and threw popcorn at me as I walked down a corridor. Kind of like in Carrie, but with popcorn. Which I will concede is not as bad.

- A girl peed on my shoes while I was in gym and told me she had done me a favor. (True, technically. They were faux-suede clogs.) 

- A boy I had a crush on asked me to literally write papers for him, which I did, frequently. Then when it was summer we were at the pool and I saw him and I was like, “HEY!” And he was like, “I’m sorry, I don’t think I know you. You look a little lost.”

- I tried to make a new (only) friend in the boy who seemed to be teased slightly more than I was teased. I asked him if I could have lunch with him and he told me I repulsed him and he would never marry me. Then he climbed on the batting cages where he always ate his lunch. 

And I could go on, but I will not. People were mean to me because it affected me in an obvious way, and that was probably amusing. To be transparent: I was totally intolerable at the time. Just, a real difficult kid. It’s not like I was getting straight A’s, beloved by at least my teachers. I was a moderate-at-best student with impossible ambitions and not a single peer confidant. (Until I finally met Jessica, who changed that, but this is a sad-sack story, and not a happy Jessica story.) I cried loudly and openly, and I wrote in my diary every single night, detailing the injustices of my particular life. In that very diary, I would repeatedly write a trope-y sad kid line: “Someday I’ll be great, and they’ll all be janitors, or whatever.”

They are not all janitors, but this is what I mean when I say that sometimes I feel that I deserve this seeming greatness. It just goes with the plot of the story, you know?

So there are these gleaming, small moments, where I feel really proud and really good and really deserving and all is right in the world.

The fraction of these moments relative to all the other moments in my everyday experience, however, is about 0.03 percent. That’s not a very high percent.

You may be wondering what I am doing the rest of the time. Here is a list. (It seems that this post is going to be pretty list-y).

- Feeling like good things are happening to me and I do NOT deserve them and I should tell everyone in my life to stop being nice to me because I am a cheat, a fraud, and a loser.

- Feeling like good things are NOT happening to me.

- Feeling like, objectively speaking, good things are happening to me and I need to be appreciating them more, and why can’t I just be present like that skinny yoga teacher from last week? And why does she get to be so skinny and I don’t? Fine, I’ll eat a bagel to feel better. 

- Watching television / reading trash.

The internet is a place to brag about all the successes in one’s life, and that’s a well-documented fact. If you believed social media, you would hate yourself all the time for all your inadequacies and failures. If you are a person posting your success, you check back on your post, hoping to experience the high of more success in the form of Likes or Hearts or Retweets or Flying Doves. (Whatever, I don’t know. It's such a cliche, but there truly are social media platforms that kids today are using that I have literally never heard of. Ughahgdasdjfas, aging.)

Sometimes you can go to the internet when you are extremely sad, but it has to be EXTREME, and you kind of have to be the victim of something. Maybe you are depressed, which isn’t your fault, because chemicals. Or maybe someone or someTHING or some institution was horrible to you. Or maybe you (like me!) need to tell everyone how much you hate yourself. People do NOT go to the internet to talk about failing. It’s just not what it’s for.

Hey, internet! Here are some of my most recent failures:

- I got an email from an editor of an article I was sure I had already locked down saying they were going in another direction with a different writer. 

- Three! Separate! Rejections! From! Lit journals! (In one day. That’s always how it is, like they plan it that way to discourage the bad writers all at once with their collective power.)

- I was told I was not a good enough journalist to do journalism, and I should stick to bloggy stuff. (Sure, ok.)

- I am constantly — CONSTANTLY — OBSESSIVELY!!!! — trying to lose weight, and I do not ever lose weight. We (we as in, like, society) don’t talk about this anymore, so it’s pretty controversial to even bring it up here. You, the reader, are thinking that I do not need to lose weight. Or maybe you think I do, but you still want to tell me that I don’t need to lose it. I don’t need to hear this. I will still constantly and obsessively want to lose weight because female programming has BROKEN ME FOREVER. 

- And, on that note, I would like to be able to do a pull-up, but I cannot do a pull-up.

- Nor can I draw a convincing owl, even given a full fucking week to pull it off.

- Nor can I make friends when at adult summer camp. Seriously: the summer camp adults look at me the same disdain as the seventh graders in previous parts of this post. 

THAT’S JUST SOME OF THEM. I can’t even BRING myself to LIST the more excruciating ones, because I don’t want you to know. Partially, I don’t want you to think I even TRIED. Success is supposed to be kind of flung at you. People should believe that you are so naturally talented that the deciders of the world are banging at your door ALL THE TIME, demanding that you do a thing for them.

I am published “in” the New Yorker (online only, folks). My pieces are “in” the Shouts & Murmurs section (Daily Shouts, an online-only daily publication.) This was my life dream, and I was excited to brag about it. I did. If you are reading this blog post, you probably heard me brag about it.

I need you to know that I had, like, twenty things rejected before the editor finally said yes. This also happened with McSweeney’s Internet Tendency. Just, rejection after rejection after rejection. I feel like with the New Yorker, the editor was simply tired of hearing from me at some point. 

It’s not cool to tell people that part, but PEOPLE SHOULD KNOW! Because I have a hunch that it is true for even the most successful among us: rejection after rejection after rejection. This is how the world works. It requires DEEP bravery to try to do something, and invariably, you will fail. And failure does not ever (EVER!) feel good. 

Early-on, I tried this Pinterest-y writing challenge where a person attempts to get 100 rejections from publications in one year. The people who came up with this idea SWEAR that it will get you to feel excited to get rejected; or at the very least, it’ll numb you out. This is ridiculous and it is a lie. Rejection always feels horrible, and it never gets easier. I may be more sensitive than others, but it is possible that so are you, and you are looking for a little company. At least there’s the two of us in this club, friend.

Like, earlier today, I went to the office at this adult summer camp and asked if I got a free t-shirt. Because there is a sign up in the dining hall that says that fellows and staff get free t-shirts. I am a TA, and I had to go to a staff training, so I thought that maybe I would be included as “staff." So I asked at the front desk, and the lady talked to me like I was an injured lamb — an unusually stupid but nevertheless injured lamb — and she said that no, TAs were not staff. TAs would need to pay for their t-shirts. That was all she really said. And I went into my bedroom and CRIED, because I hated the thought that this woman was sitting there thinking, “Oh, poor wounded lamb fake teacher. She just doesn’t know any better. She is so low on the food chain, but she cannot see her place.” That is how low-level the rejection has to be for me to ACTUALLY CRY WET TEARS OUT OF MY EYES.

I tell you all this because it INFURIATES me that I am so reactive when I fail. Because there are so many things I do not fail at! And there are lots of wonderful things that happen to me all the time. And at the end of the day, I don’t think I would want to trade places with anyone, not even a celebrity. This is because I get to love the people I love (and I love them!), and I am basically living my truth, and no one in my life is incredibly sick, and things are objectively good. (Once I was rejected by a pub who told me to “scale back on the adverbs.” They were definitely right, but fuck that.) So how come I can have these horrible feelings of despair and self-loathing at the drop of a proverbial hat?

I’m not sure. It is what Buddhists call the “second arrow.” First, you feel bad. Then, you’re mad at yourself for feeling bad. It is hard for me to eliminate the second arrow. I think I’m secretly sort of fond of it; it makes me feel safer. At least if I hate myself for this terrible behavior, then you know that I know that the behavior is terrible. 

I said all this to Luke earlier today, while crying about ANOTHER REJECTION, and Luke said what I knew he’d say: “You’re having a feeling. Your feelings are always valid.”

See what I mean about getting to love the people I love? (If you feel lonely, you can love Luke too. He seems to have space for a lot of love.)

But I wished, just then, that I did not feel like such an idiot, or so alone. And my experience is that when you think you are alone in something, you really aren’t. The internet should be for that. It should be for connections that heal us; not ones that make us feel like nothing we do will ever be good enough. 

So, in conclusion, to fail and keep going you must:

- Fail

- Feel like shit

- Honor your shitty feeling, because you’re feeling it, and that’s fine

- Talk to someone about it if you want. If they’re a halfway decent person, they won’t think less of you.

- Try again

- Fail again

- Repeat some of the steps above

- Know that even people who brag tirelessly about their accomplishments fail constantly. You’re not alone in it.

- Cry, maybe.

- Sleep. Sleep can really help.

- Don't end essays or pieces of writing with "in conclusion" anymore; also do not end them with lists. Pieces that do this will always be rejected.