Why You Should Fail At Things A Lot

My little brother didn’t get a summer job he interviewed for. He really wanted it. He kicked butt in his cover letter, and he was at his best in the interview, too. Afterwards, he didn’t want to talk about it, and I didn’t know what to say. It’s a weird thing, when you’re like, “give me more responsibility. I want to work all day instead of being a kid,” and the world is like, “Too bad. You have to stay a kid.”

I was worried he’d blame himself.

I’d really wanted him to get the job, because I really didn’t want him to learn to stop trying. That’s what happens sometimes after you get turned down enough. You throw up your hands and you say, “Whatever!” and whatever you decide to do next after that “whatever” is usually not anything worth remembering. It usually involves a lot of TV shows that you’ve already seen and weren’t totally crazy about the first time but this time they feel a little more nuanced. Unless you have incredible fortitude of spirit, and honestly, I’m not even sure what that is. I may have just made it up.

I felt called to say something. The way that I feel called to write to A.O. Scott and tell him that his review of Snow White and the Huntsman was really, really wrong. She is not a feminist symbol. She barely even talks. But maybe even more than that. So I sat my brother down, the way I thought a good big sister would, and I said, “Um, so, I thought that—well, I wanted to talk to you about something,” in my confident, charismatic way. He looked at me blankly. I said, “I want to talk to you about failing.”

And then I told him about how I didn’t get this internship that I applied for in grad school, even though my competition was probably nineteen-years-old and the position was basically that of an unpaid secretary. I did three rounds. To not be paid. And then I got rejected. But that wasn’t really a big deal. That was just the warm-up. I told him about how, for over a year, when I started writing almost fulltime (although with two part time jobs to keep me making some money and feeling some legitimacy), I did nothing except for fail. I mean, in addition to working. I received a constant string of rejection letters, and that was when I was lucky. Most people I pitched ignored me completely. Even the bloggers I tried to form connections with often ignored me. I wasn’t big enough, and I had no idea how to get there.

When I decided to be a writer, you know, as a real thing, I was about to enter a very dark period of total failure. I didn’t know it then, but it would last for well over a year. Which is a long time to be totally failing. (Although, if you want to get technical, I’m probably still failing now, in plenty of ways.)

But there’s a hopeful message here, I told my little brother, who was laughing at me a little, looking slightly confused.

That whole time, that I was failing and being depressed and stuff, I kept on going, doing the thing that I knew I loved. I chose my thing. And I did it in my own way. And I kept doing it, with my teeth gritted and my fingers stuck to the keyboard. I kept writing until people read me. Until they told their friends. Until someone finally wanted to publish something I’d written. Until someone else did. It was not luck or magic or great/any connections, for what felt like forever. It was just me, doing it anyway. Resolute and miserable and fiercely determined and totally unprepared and earnest and helpless and tiny.

And if I can do it, Gabe, so can you. For sure. With all of your talent and your quick brain, and your brilliant wit and your natural ease with people. You can do it even better. I am this awkward, anxious, uncertain person. You make people laugh uproariously with one sentence.

If I can do it, it is definitely doable.

But I think it’s better, when you begin, to know that you will fail. Not just a little, but constantly.

And I think that if you have even the smallest opportunity to do what you love anyway, you should take it. Because that’s what makes it worthwhile. Doing something that you love for itself, and not for the things that it might or should or someday probably will get you.

So don’t wait for someone to accept you. Do something you love anyway. I mean, keep sending in those applications, of course, but at the same time, if you possibly can, try to find a thing that you can work on just because you like the way it feels to get better at it. Just because you feel that you know yourself a little better the more you do it. Just because you are already pretty good at it. Chances are, it relates to your dream job anyway. Think of it as an investment in your future. And then, when you fail, keep going. That is absolutely the only way to get to success. And actually, I think it’s a kind of success itself.

I told my little brother that when I think back over the things I’ve done (in my long and almost certainly esteemed twenty-six years of life), I am mostly proud of one thing: not giving up.

It’s a pretty typical thing to be proud of. I’m not claiming to be original here.

But I will say this for myself: I have gotten a lot better at failing. I am no longer crushed by a rejection letter. I knock them back like tequila shots. Ooh, it burns for a second. Ahh.

(No, but really: I can’t do shots, I’m a baby about them.)

I am thankful for little steps forward.

But most of all, I know something really important about myself: I am the kind of person who won’t go away. Who won’t shrug and leave. Who isn’t going to shut up. Who ultimately believes that she has something to offer. Who is on this private mission to write things she finds worth writing, and who can’t be stopped from writing them. Who, though tremblingly insecure at times, must still have this secret fortitude of spirit, because otherwise, why keep going?

That sounds like a person I’d like. Which is cool.

So that’s what I wanted to say about failing. It’s a great feeling, to know that you can fail and keep going. It’s worth a lot of failing to get there. So go ahead and fail! Do it some more! Do it lavishly! Try everything you want to try! Put yourself on a path with a view you really like, and start walking and then– just walk some more.