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10 writing hacks to overcome perfectionism and just start spitting it out


Last week, I hosted a writers workshop for the whole company. It was something I’d been talking about with Kyle (one of the Keen founders) for a while, but it had been hard to get started. I felt performance anxiety to make it amazing and shower everyone with genius words of wisdom about how to be totally awesome as a writer. That kind of pressure is tough, but it’s so hard to get around it when you’re in charge of something and supposedly an expert.

But then Kyle said something that made it all feel okay: “Don’t worry about it. Just make it a prototype.”

A prototype, I thought. That’s genius. So it doesn’t even count! It’s just for practice. Suddenly I was excited instead of scared. And I realized I had just found inspiration for the theme of the workshop: Perfection Is Poison.

I latched onto this theme because I’d noticed I wasn’t the only one in the company who got tripped up by perfectionism, especially when it came time to write something. Impostor Syndrome, Writers Block, Generalized Creative Anxiety, they’re all close cousins on the neurotic freakout spectrum (NFS).

The question for the writers workshop was: how best to overcome them? Could inspirational ideals be helpful? I guess, maybe. But what about cheap tricks and gimmicks? Could they help, too? I was pretty sure the answer was yes.

So here they are: the top ten writing hacks to overcome perfectionism and just start spitting it out.

1) Call it a prototype. Whatever you’re writing, decide from the start that it’s just for practice. It doesn’t count. No one even has to see it. You have no plans for it. It has no title. It barely exists. So just dive in and type around and see what happens.

2) Pretend it’s an email. You know how it’s so much easier to write in your own voice when you’re just sending an email? Okay, open your email, pick a friend to put in the To: box, start Dear so-and-so, I’m writing up this thing and I just want to make it sound natural, so you’re my secret guinea pig/muse/recipient/conspirator. And you don’t even know it! Then keep going.

3) Have a conversation instead. Kind of like emails, conversations have that way of being so damn conversational. They just can’t help it. Jot down some notes about your idea and get someone to listen and ask you questions. Have them write down the phrases they like best. Or just record it.

4) Break it down. 1,000 words too much to ask? Try just answering a few questions, ideally in pen. (Hand-written always feels lower stakes, especially if your handwriting is horrible like mine.) Who are you talking to? What is the one thing you want them to know? What are three examples/variations/anecdotes about that thing? Get that down and now you have something to aim for. (You don’t have to call it an outline. That’s too formal and confining. Feels too much like middle school.)

5) Share it too soon! Yes, before it’s ready, when it’s still obviously rough, before you’ve had a chance to edit out the best phrase because you decide it’s stupid, and before you’ve worked on it long enough to have any reasonable expectation of “quality,” let alone “perfection.” Chances are your reader will find something great in there to organize around. Worst case, you’ll be able to say, “I only spent an hour on this. What do you expect?”

6) Get a buddy. I know, it’s not the gym and we’re not doing squats or jerks (or whatever athletes do at the gym. I’m a writer; I have no idea). Point is, it’s easier to share something too soon if you’ve got someone else doing the same thing. Mutual vulnerability and accountability.

7) Do a reality check. What’s the thing you’re most afraid of? Name it. Ask someone if it’s rational. For me with my writing, my biggest fear is that I’ll write something lame and everyone who previously admired my writing will suddenly say to themselves, “Oh my god, we were so wrong! You have no talent at all! We were giving you credit you don’t deserve! In fact, you are completely worthless! Not just as a writer. As a human being!” At our workshop, I asked my colleagues if that is how they would respond in the event that I wrote something that wasn’t my best work. They laughed and said, “Of course not!” (but half of them acknowledged they had the exact same fear).

Note: I’m not saying I won’t write something lame. In fact, this might be that very thing. But it’s not reasonable to think that your whole reputation as a writer and human being is on the line every time you write a new sentence.

8) Specify what feedback you want. You know what’s dangerous? Showing writing to someone and saying, “Well, what do you think?” In the absence of any guidance, that reviewer may have a field day on a worm can you didn’t even know was in the pantry. (Triple-mixed-metaphor: 10 points.) If you’re mostly curious how they react to the topic, ask for feedback on that. If you’re definitely sold on the topic but curious about the flow, ask how they think it flows. If you plan to publish this afternoon and want a set of eyes to look for typos or glaring errors, ask for that. Help the reviewer be helpful.

Not sure what feedback to ask for? Try these two questions: 1) What do you like about the piece? 2) What is unclear or unnecessary? (Feel uncomfortable asking those questions? Say you got them from a blog post.)

9) Ignore all this advice. If you’ve got a system that works, fine, do that instead. But then why did you click on a post with this title?

10) Don’t have 10 things in a list. It’s very tempting to go with ten, but it feels inauthentic and forced. Avoid it.

I hope some of this was helpful to you. Full disclosure, this is my fourth attempt to write something to share the most valuable takeaways from our workshop (second attempt written entirely inside a Yahoo mail window). I’m going to send it to the friend I put in the To: column now because it’s still too soon to share it. I’d have to be crazy to send it now.

If you have any sneaky tricks to share, please add them in the comments (assuming I go ahead and post this later). And if you feel like attacking me as a human being, go right ahead. I can take it.

Now please fire up your email and start working on a prototype. It doesn’t count and no one will even know.