[I wrote this post for my writing students on a separate blog, but the same principles apply to other endeavors--like photography and fashion--so I thought I'd repost it here with an addendum.]
One of the many challenges of writing is learning to let yourself write badly. This doesn't mean that you should write badly and leave it that way; it doesn't mean that writing badly should be a goal in itself. It does, however, mean that there is a stage in any writing project where it is okay to just write without worrying about it being perfect or even good.
For many writers, this is really hard. You may feel like you have to start from nothing, from just the wisp of an idea in your head, and somehow leap from that to a polished essay that you can turn in (and hopefully get a good grade on). Or you may feel like you should be fixing things as you write your first draft and making sure to organize everything neatly when it first hits the page; you may be planning to turn this draft in and therefore are trying to do everything at once.
But a leap from nothing to something is not the most effective way to write. In order to wind up with the desired final product (a polished, well-written essay), you have to start with something less than polished and well-written: the rough draft.
It is at this stage that it is okay to write without worrying about how well you're writing. It's okay to suck. All you need to do at this stage is get your ideas down. You will have time (because you have made time by starting before the night before it's due) to fix things. My early drafts are fragmentary and repetitive. I use words that I know won't really work in a final draft just to fill the space so I can keep going. I'll come back and change them out later. I insert reminders like [examples] or [transition] to tell myself that this is a place that will require a specific kind of work, but I don't try to do that work immediately. I'll come back and write those bits later. I ask myself questions and argue with myself. I will make decisions and smooth those inconsistencies out later. This process is vital to my writing, no matter how ugly it looks; it gives me a chance to record my ideas, to see where they already look kind of good and where they don't, and to build a foundation for the stages that will come later (rereading, reorganizing, rewriting).
The best ideas and writing don't just appear fully fledged, after all, but require development. And the people who are most skilled at whatever they choose to do (not just writing, but art, sports, etc.) got that way by working through not knowing what to do, not being able to do it well, and, sometimes, just generally sucking. So if your writing is great to start with (or if you think it's great to start with), where is there to go? What is there to learn? You may find, if this is the case, that you aren't really challenging yourself, that you aren't really growing as a thinker and writer, and that your work will suffer as a result.
So dare to suck. Dare to write what you really think--even if it's confusing. Dare to write badly and chaotically. The beginning is for getting ideas out of your head and down on paper in some form. It isn't for great writing. That comes later.
Fashion and photography have worked the same way for me. I try things and they may not work. I take note and try something different next time. I have lots of old outfit pictures that I'm not terribly proud of but that are a necessary part of my fashion development. I look back at the early pictures I took and posted on flickr, even the early stages of my Project 365, which was just over a year ago, and I see how much I have grown as a photographer. A big part of that growth is wrapped up in not just doing what I'm already comfortable with but trying new things at which I might suck.
I am, therefore, a huge proponent of daring to suck. It can be scary to try something that might not work, but there's really no other way to learn.