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How can you ever start writing something that's extraordinary if you never start writing at all? Do you really think Mark Twain started out writing Huckleberry Finn and Tom Sawyer? It is a skill that requires effort to become good at.

Oh, I agree. You're absolutely right. I know that the perfect is the enemy of the good, but just knowing that doesn't make it easy to get over the psychological hurdle.

The same hangup keeps me from trying many of my software ideas. It's a feeling that I'm constantly learning to fight.

This is basically EXACTLY how I feel. I sometimes think about starting a blog, to showcase things I've worked on, or interesting things I've read about, or new things I've learned, but I often think that it wouldn't be original enough to warrant doing. The thing is, you don't know until you try...

You should read Natalie Goldberg's Writing Down the Bones. She describes exercises to help get over these feelings, and gives you permission to suck. Or rather, convinces you to give yourself that permission.

I can totally relate to that. That's EXACTLY why you should start immediately. To overcome perfectionism.