When do you finally decide your piece is good enough to send out? After all those rewrites and what not, I do a quick reread just before sending it out and I still find something I’m not happy about. Then, I don’t send it out at all. So, any tips on getting over your fear?
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Ah, the eternal internal debate. My feeling is that this fear comes up in three kinds of situations:

1. You’re new to freelancing, so haven’t yet proven to yourself that you have what it takes and need someone to give you that reassurance (or tell you that you suck and give you pointers on how to improve).

2. You’re a constant worrier and a perfectionist and no matter how many times you’ve revised it, you’ll find flaws with your work.

3. There’s that odd piece of writing that’s giving you grief, and you’re too close to it to make an accurate judgment about whether or not it’s any good.

I’ll tackle Situation No. 3 first because that’s where I’m at career-wise. I’m mostly confident in my ability to write a good article, but there might be that beast of a piece that’s a little tougher than most and I need help with. Like I mentioned yesterday, my own critique group and personal network have been extremely valuable to me. When I’m struggling with something, I’ll usually send it to them if I have the time. I’ve been part of my networks for several years now, and trust their judgment.

When struggling with pieces on very short deadlines, I’ve been known to ask my photographers for their feedback (who better to judge than someone who was on assignment with you?) and I’ll also typically just turn to any of my close journalist friends and ask them to take a look.

But you don’t need to be best friends with another journalist to feel confident about your work. If you’re in Situation No. 1, consult the list of critique groups I posted yesterday, join a few and see which ones feel like they’re going to be most useful. As a new writer, the right critique group can be such a great resource– members might be able to not only help point out flaws you didn’t know you had, but look at your writing as a whole and see if there are any holes in your logic, etc.

Situation No. 2 is tricky, and the only solution to that is to assign yourself a finite amount of time per piece and then just let it go. Of course you’re going to keep finding flaws with your writing the more you look at it– that’s what we do! Hell, I can’t even look at some of my past work without wanting to take a red pen to it, but that’s part of growing and improving. At some point though, you’ve done the best you can at this moment in time, and one comma here and another modifier there won’t change that. When you start making changes that no one but you would notice, it’s time to let that work out into the world.

That said, I should make clear, that I’ve never sent out something I’m not happy with. If a piece doesn’t feel right, or has clear structural problems, or is missing something, I will do the best I can to fix it. What I don’t obsess about is small tweaks, but overall, I have to be confident that I’ve done the best I can before I submit it to my editors. After all, that’s exactly what I’m paid to do.