A writer who wishes to remain nameless sent this: “I hate talking money when it comes to my writing. I wanted to do this for the art, not the paycheck! How can I get over my reluctance to talk dollars?”
I realize some authors are reluctant to talk about money issues, but it’s necessary if you’re going to get to know the business. When I was a free-lance writer, I noticed that publishers (both magazine and book publishers) tended to put me on the bottom of the pay ladder because I was a small free-lancer. I once called a publisher to complain that I hadn't been paid, and the response was, "Oh. Yeah. Sorry. Guess we'll get you next quarter." To them, it was a measley $1500 they owed me. But to me, it was MY HOUSE PAYMENT that month. So, yeah, I eventually got over my reluctance to talk money with publishers.
That means you have to know what you're worth (in terms of money-per-page or money-per-hour), and you have to be able to share that with others. The good news is that it gets easier to talk about when you have a pretty good feeling of your value. I mean, if you know you should be making $3000 per month, and the publisher asks you to work on a freelance project that will take two months, it's much easier to say, "I'll need to make about $6000 for that project" than to take a wild stab at a number.
So let me suggest something... Figure out what you'd like to make from your writing in a year. (You need to be reasonable. Don't say, "A million dollars" unless your name is James Patterson, Suzanne Collins, or George R.R. Martin.) Let's say you think it's reasonable for you to make $18,000 this year from writing. That means you need to make, on average, $1500 per month, or about $375 per week. If you start looking for ways to generate some income with your writing, that may not be so far-fetched. And if you land one book contract that pays an advance ten or twelve thousand, the goal becomes much easier. But start by figuring out what "financial success" is to you, as a writer.
Often writers act like they can't talk about the money they make ("I signed a confidentiality agreement!") -- which may be true, but only in terms of sharing the wording or the deal you received. It may not be a violation to talk honestly with friends about how much money you're making with your work. That's one of the reasons I encourage writers to make friends in the industry, attend conferences, and learn from other writers. It's so much better to have some friends who understand how tough this industry can be, and talk with you openly about what they're doing to earn income. (And by the way, when I was a freelance writer, I found one excellent way to feel better about my income: Exaggerate. You just feel better when you can look at someone at a conference and say, "Oh, yeah, I made $50,000 via my writing last year." Just a thought...)
Let's face facts: If you're uncomfortable talking about money, or you can't be bothered nagging that publisher who keeps forgetting to pay you (and there are a some publishers who struggle with this), then you need to find an agent you're comfortable with, who is competent with both numbers and negotiation, and talk to him or her about handling this for you. You'll find it's worth it to you.
But back to your question: If you're uncomfortable talking about money, you probably either need to give that concern over to someone who isn't, or you need to find a way to get comfortable with the topic by introducing it to other writers and starting to share your stories.