You’ve done the work, and you deserve to be paid. But sometimes asking a client to actually pony up and send you the cash can be uncomfortable. Worse, you may find that while you’re confidently sending out invoices, they’re not getting paid nearly as quickly as you’d like – and sometimes not at all.

If you’re just getting started freelancing or you’re finding yourself buried in unpaid invoices, this can become a critical situation.

Take a closer look at these tips about when you should ask your clients to pay for your work.

Ask According to the Contract

Before you ever begin doing work for a client, you both need to sign a contract that makes invoicing and payment terms clear. This should include when you’ll be sending them invoices, how many days they’ll have to pay, when payments will be considered late, and what penalties they’ll incur when they don’t pay on time. This protects you, but it’s also convenient for your client.

The client will then be able to make a much better projection of how much money they need to have available (and when) in order to pay you what you’re due on time. This means no awkwardness or hurt feelings; any disputes can be settled by referencing the contract.

Ask as Often as You Can

There’s no reason not to invoice weekly. If it seems like a hassle, you’re probably doing it wrong. With hundreds of online invoicing services to choose from, you can automate your invoicing so that it’s far easier than ever before. Invoices can be generated automatically so that all you have to do is click send.

It’s easier for a client to ignore a bill that only comes once a month; when an invoice comes every week, getting you paid is fresh on your client’s mind and they won’t easily forget that you’re waiting on them.

Ask on the Weekends, Ask on the 1st

Studies of more than 30,000 invoices suggest that the ones sent closer to the beginning of the month (say the 1st) and on weekends are paid far more promptly than those sent at the end of the month or on weekdays.

If cash flow is ever an issue for you, every single day counts; here’s we’re talking about differences of more than a week. While it might seem insignificant, choosing the time of month and day of the week to send a bill can actually make a huge difference in how promptly your clients pay.

Ask in Advance

In some industries, especially service industries, you don’t actually have to wait until the work has been completed. You may want to consider asking for 50 percent of the total fee up front (a retainer) and 50 percent once the job is completed. If this is a big problem for your client and they balk, they may be sending you a clear signal that they’re not actually planning on paying you at all (or, even if they have good intentions, that they’re unlikely to come up with the money any time soon). You’re running a business, and unless you’re doing pro bono work for someone, your clients need to pay you in the manner you request.

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