How to be more critical of my own work?

I’ve gotten to where I’m better about being critical of my music, but I’m really bad about picking apart my writing unless it’s coming from someone else. Bad part is, that someone isn’t always there. I’m becoming more and more interested in political speech writing, but it’s hard for be to see if this is obviously bad or hacky writing or if it’s something that’s actually passable. I’m trying to develop good analytical skills but, often, when I’ve finally gotten it written down, it stays. It makes sense in my head and flows but my best work has usually come after a revision or as a random late addition. Only a few times have a gotten a perfect draft out in one big rush of writing.

Does anyone have any help on how to pick apart your own writing? I already read it out loud an hour or so later, but I haven’t developed anything past that.

One classic suggestion is to read it aloud.

This has an amazing effect of clarifying run-on sentences, awkward dialogue, ambiguous grammar, and so on. Every so often, you might find yourself stumbling over how to read a given sentence. That’s a pretty good sign it’s grammatically awkward.

An audience helps – a patient friend or family member. But just read it to your cat, and you’ll benefit.

Also: time. Wait a bit between writing and self-critiquing. Let the heat of creativity cool off, so you can appraise the work more objectively.

Be cold and analytical. Keep asking sharp questions. “Does this advance the plot?” “Will a typical reader find this interesting?” You end up having to be a bit brutal with yourself, and you’ll find yourself deleting a lot of text you really like. Writers refer to this as “Killing your children.” Not fun!

And, finally, read a lot. Study what you read. Pay attention to how other writers handle paragraphs, dialogue, grammar, punctuation, etc. Beginning writers often serve an “apprenticeship” of this sort, consciously mimicking another writer’s basic style (not to the point of plagiarism, obviously!) When I first started trying to write, I wrote after the style of Poul Anderson. One could choose a lot worse!

(ETA: most of this applies to prose fiction, which is what I write. Speech-writing is something I’ve never tried.)

The best advice for me has been to let it sit for at least three months. Put it in a drawer or file. Don’t look at it, don’t touch it, don’t think about it if you can manage it.

Then go back and read it critically - like someone else wrote it. If it’s still familiar and personal, back in the drawer for another three months.

Now, for this to really work, you have to have multiple projects going so you have other stuff to keep you busy while that work is ‘resting’ for a while, but that’s good too.

It also really helps to have someone else to give feedback - not a friend or family-member, but a writing buddy or writers group or beta-reader or a mentor or an actual paid agent or editor. I’ve used all of those except an agent, and they’ve been way more useful than any self-editing passes I’ve ever done. At a certain point, you just need an outside perspective to help hone your craft.

Good luck!

I agree, read it aloud in a Sarcastic Bystander voice.

Tom Waits (and previous replies in this thread) have your best answer: it’s time, time, time that you need, and it’s time, time, time. The longer the better. All first drafts are crap. Everything needs to be re-written. Extensively.

For doing small edits, I find it enormously helpful to throw manuscripts into Calibre so I can read them on my Kindle, like “real” books. That kicks my critical reading up a notch, from reading on the word processor.

My main problem is developing the internal proofreading methods since when I start speechwriting, it’ll end up being something that’s due very soon and I might be working on it myself.

I advanced by miles in critiquing my own writing when I started writing the same thing in multiple voices. For example, if you’re writing fiction, trying writing it once as if it came from Mark Twain and again as if from Ernest Hemingway. Or write it once using an educated narrator and again using a childish narrator.

This exercise helped me to recognize and analyze the underlying voice in my writing. Once I recognized it, I could analyze whether it was helping or hurting any particular piece and now it’s pretty much second nature. I’ll get a few paragraphs into something and think “Right information, wrong voice.”

You seem to think that needing multiple drafts is a bad thing. I wouldn’t expect everything to come all at once. The more professional you are about writing, the more likely you see it as a mechanical process rather than a creative one. (In other words, Stephen King doesn’t sit around waiting for his muse to deliver perfection. He sets a clock and starts typing. When he has ten pages done, he can take a break.) A lot of writing is about organization, discipline and the not-fun tasks of doing things like editing and re-writing.

If you are finding success through multiple writing sessions and multiple revisions then I would recommend working on how to make those more successful. Don’t try to force yourself into some other mold.