This is a letter I just got from a reader and since it might address some of your own concerns I thought I’d use it as a post and include my answers (in bold type). My thanks to Debra Moini for letting me post it.
Here is my writer's dilemma: I thrive in a setting of structure, assignments and hanging on to every word of a respected instructor, but left to myself, I don't finish anything. If I don't finish anything, I will not send anything out and I will be 56 when I revisit this issue next year.
I would like to know what you tell your students after they've taken several writing classes but still feel like they're just beginning? I tell them that they, like all writers, will always feel like a beginner when they sit down to write and face a blank page or screen. I feel like a beginner every single time I try to write a first draft of anything.
Or, for whatever reason, they feel like they can't produce anything on their own? That “for whatever reason” might be explored and addressed. I do believe in writer’s block, but you need a lot of soul searching to move beyond it. Also, try to find a writing buddy. Maybe someone you were in class with. Someone whose writing you respect, someone you don’t have any personal baggage with. Arrange to meet once a week (or via e-mail) and give each other five minute writing exercises. Read each other’s work and offer positive and honest feedback. Give each other deadlines.
What does it take to push someone out of the writing nest after they've been safely tucked under an instructor's red pen and numerous rewrites?
(See above.) But ultimately if they’re serious about writing, they simply have to set goals and learn to fly on their own.
How does one find the courage to believe in themselves enough to go forward with or without the encouragement of others? Being stubborn is the key. You don’t need to believe in yourself or even have encouragement, all you have to do is write everyday. Maybe just ten or twenty minutes. Make it a ritual and don’t give yourself a choice. Right now I'm trying to write the last chapter of a novel I've been working on for years. A book that was turned down twice by my agent already (she hasn't seen this latest version.) I am convinced it's an impossible chapter to write. And the first attempts I've made are truly awful. Plus no one really, really cares if I write it or not. Sometimes only sheer stubborness keeps you going.
When did you first realize that you wanted to be a writer? When I was six years old and wrote my first story.
What were the steps you took to get where you are today? I read and I wrote. A lot.
Who looks over your shoulder to help you through the writing process? All the authors whose books sit on the shelves surrounding me. I also have five people I show my work to before I send it to my agent. I respect them all (they’re worth their weight in gold and rubies), and they won’t hesitate to tell me when I’ve veered off in the wrong direction.
I've written to you before and hope you don't mind me writing to you again. I know you're a busy person. And you don't know me. But I love your work, I look forward to Writing Time and I enjoy the blog. And since I don't, as yet, have a writing community, I will appreciate any guidance that you are able to give. Those authors up on the shelf are your real writing community. Also the people you’ve been in classes with and the people who are reading this on the blog right now.