Well, if you write the way I do, which means that you start something and you rewrite it, especially the beginning part, you rewrite it time and time and time again, at some point you feel, not that it’s beyond repair, but that there’s nothing more you can do to fix it. In other words, as far as you’re concerned, that’s what you were going to write.

I move back and forth. The Tribe book is easier. I have a proposal and a plan for that, so it’s easier to know when that’s done because there’s a hard end. There’s a certain amount of chapters, and that whole thing. But poetry books, at least in my experience, those tell you when they’re done. My first book told me when it was done. It told me when I had mined everything I could out of the emotional landscape I was trying to create, and it pointed me to an exit strategy. With poetry books, I have been lucky to have my poems do that. My poems tell me how they want to live in the world, when they want to live in the world, and when they’re done being played with… Sometimes, it’s over the course of a month with one poem, or sometimes it takes a little longer than that. I think the hard work is knowing when to pull yourself back so you don’t overextend or let your projects blend together.

You just have to call it eventually. [For example,] technically speaking, yes, our September Issue is done. It has shipped. But do I feel finished with it? Never. We were ambitious with this issue—we decided we couldn’t platform just one, “face of fashion” and instead went with three exciting covers who each have added something unique to the conversation about style. Having one solid image for a magazine cover is one thing, but it’s another to say something through three rich stories. It was an exciting challenge, and I give my incredible team a lot of credit for their dedication and endless hours. I can’t wait for you to see it.

That’s a really good question. I don’t think you ever know; you just have to make a call. Finishing is acknowledging that there’s no further progress to be made at the current juncture. If you sit on a song for 20 years and come back to it with all the wisdom of your life, you could probably write a better song, but objectively, you have to get it out into the world in order to continue to live as an artist. So, there’s a sense of: “well, this is as good as it’s gonna get for me at my level right now.” Sometimes you realize that early, but it can take a long time. I think deadlines were invented by God to make art possible. I don’t think I could finish anything without a deadline, self-imposed or external. With the book, it was just: these people at Penguin, they don’t know me. They have no idea that I can’t do this. I have to do it because otherwise they’ll know that I can’t do it.