Why do you want to be a writer? No offense, seriously. But for me, I want to write because stories come to me and need to be written. It's not "I want to be writer" so then I have to struggle with how to be a writer and then struggle with what I want to say (since writers have to say something) and then struggle with story ideas, all so I can be a 'writer'.
For me it's more just going through my day, watching and participating in life, something happens, or I reflect on something, and suddenly the idea for a story pops into my head. I spend some time thinking about it and it grows, then I have to write it down.
Do you want to write, or be a 'writer'? They're different. Here, let's look at your questions.
Do you have any advice for
overcoming the fear of failure/being
Do you have any thoughts on how to craft a plan for becoming a writer and
actually getting things done beyond
brainstorming? (What should "step one"
How do you read masters of the genre (I started reading John Le Carre
today) that interests you in a way
that doesn't lead to the reaction,
"I'll never be this good, so why try?"
1) You shouldn't worry about pleasing anonymous strangers. Try to write stuff that you think is good. Then show it to people and listen to feedback. Some will be good and some will be bad. Learn to distinguish. If you write based on 'fear of failure' you will base your writing on trying to figure out what will be popular. That's the surest way to fail that there is. You're an artist. An artist is one mind, one vision. Listen to yourself. The key to being a writer is trusting your own judgment about what is good. If you keep looking to other people to tell you about your own writing, you'll fail.
2) Plan for becoming a writer? Ok, here: Write a book, get it published. That's it. At that point, you're a professional writer. If you mean a plan on how to write, here it is: you sit down at your computer and write. If you don't know what to write, then you need to think about it. There's no substitute for thinking. If you want to write thrillers, then think of a cool thriller plot.
Here, I'll give you one I thunk up 10 seconds ago: A woman wakes up to discover she's undergone a sex change operation and is now a man. More, her whole family has been murdered. She discovers that she is part of a UN experiment on gender meant to unify the sexes into one unisex type and relegate all reproduction to the authority of the UN, part of their evil plan to take over the world.
Could you take that, or some idea you thunk up, and turn it into a book? If not, why not. What I just wrote is the kernel of a thriller story that you, as a thriller writer, will think up, fill out, and turn into a book. When you get an idea for a book, it will take that form. That's what an idea for a story looks like.
3) No, I never think "I'll never be this good." because I never think that writing has only one measure, one dimension. Le Carre has his strengths and weaknesses. So does any writer. Personally, I think Le Carre's characterization is weak. I don't find his people worth knowing. Again, I keep coming back to one thing: what do you want to say? What do you want people to feel when they put down your book? Do you have any idea?
Why do you want to be a writer?