Etiquette is important when you want to establish yourself as a professional but it should not be at the sacrifice of your business.
Don't be afraid to ask about money early in the negotiations with a client or potential client. It's to your advantage to approach the subject with confidence and without apology. You both know the score and that you are a freelance writer who writes to earn.
I often see opportunities that are paid with byline or that are a little low paying but offer a lot of good for your career but too often, I think freelance writers are afraid of hurting their image by asking about money. Most freelance writers do it for money despite their love for the craft so it's important to take the right approach on the subject to minimise your exposure for loss.
When you negotiate a writing project, you need to have clear expectations of what is expected of you and when you'll be paid. It's much easier to do the job you're being paid to do if you know up front what to expect. Here are a few money related tips for you:
New Clients And Writing Project Deposits
If it's a new client, ask for a deposit and don't start the job until the deposit clears. If they are frightened off, either they are new to the industry and not convinced you won't rip them off or they are not to be trusted anyway. If you establish yourself as a professional and treat the negotiations as such, new clients won't be suspicious of your motives. However, you must be sure you deliver on time when you have been paid a deposit or you probably won't have repeat business.
Milestone or Interim Payments
It's ok to arrange interim payments if it is a long project that eats up a significant amount of your time. You won't know if it's possible unless you ask. It can be difficult to write for several weeks without money coming in and frankly when it's a new client, it's easier to chase for a week's pay than four weeks of pay so it's something to consider. Milestones are also a great idea for ensuring that you are on target to meet the client's expectations. Better to do a rewrite on a week's work than a month's!
Invoice as soon as you send the job. If I'm being paid by PayPal, my invoice is a PayPal invoice. The minute my assignment is in, I'm making arrangements to be paid.
I like the PayPal invoice as it tells them immediately, "The work is in, now pay for it!" I also like to initiate the payment myself with the PayPal request instead of waiting patiently for the client to manually pay me. They don't have to look up my e-mail address or ask me for my PayPal e-mail account and the clients have the ability to pay me with the click of a button instead of manually paying me and if I need to, with the click of a button I can send a 'reminder' notice. I rarely simply use the reminder notice on PayPal, mind you. I'd rather ask the question and give the client an opportunity to answer me.
Following Up On Past Due Invoices and Understanding the Details of Payment
If the buyer is not meeting their agreed commitment, it's ok to follow up. Don't stew and worry about your money, find out what's happening as soon as they're late. If a client falls outside their normal habits for payment, I send a quick and polite follow up e-mail. There's nothing wrong with this and it's not bad manners. As freelancers, we don't necessarily have a weekly paycheque so we live by the ETA our client gives us for our payment.
My last suggestion is that you find out how they will pay you up front. This is something I've struggled with a few times with clients. If they're sending a cheque, you know your own bank's policies and to account for snail mail but if you are expecting a PayPal payment and you get an e-check instead of a live payment, it's a lousy feeling when you weren't expecting it. Depending on the country you're in and the country the client is in it can take weeks for it to clear so when it's indicated that you'll be paid by PayPal, there's nothing rude about asking if it'll be a live payment or an e-check.
Talking about money isn't rude when you are a freelancer and on the contrary it's a detriment to your livelihood so approach the subject confidently and professionally.