Many are drawn to the world of freelancing because they don't care for the oppressive structure of the workplace. Freelancing bids you to forget the nine-to-five schedule, the commute, and everything else that goes along with it.
It also means that you're on your own for many of the operational responsibilities of a business. You're Creative, Accounting, Management, HR, and Facilities, all rolled into one.
Invoicing, in general, is already the worst part of freelancing. You've done stellar work, and now you have to chase down your money. It can be nearly impossible if you don't like invoicing in the first place.
Here's how to make it work without too much work:
Pick 2-4 Days per month to invoice
If I had to invoice each project on a different day, I'd go crazy (and I'd never get paid). Look at the billing cycles of your clients and how often you need to get paid (if one client pays weekly, it may be worth it to set a day each week to submit that invoice).
Otherwise, clients usually want invoices on the 1st and the 15th of every month. Set those days aside as "invoicing days." You're more likely to get the invoices done when you're not trying to squeeze them between "real work." Plus, this sets up Invoice Day as your own personal office holiday, when you get to take a break from your regular work load.
In order to enjoy Invoice Day to the fullest, you want to eliminate redundancies. There are a few ways to do that, depending on what type of accounting software your running for your business. Quickbooks is great because it automatically generates invoices for you, once you have entered information about the job (it will also help you chase money that is owed to you).
If you're not ready to invest in accounting software, you can also eliminate a lot of busy work by using autofill spreadsheets in Excel. Like many tasks in excel, it may seem daunting in theory, but once you break down the steps, it's pretty easy. Directions on putting together an autofill spreadsheet can be found HERE.
Prioritize clients who pay on time
Don't break your back for clients who pay you late. Comcast doesn't accept excuses for late payments and neither should you. Invoicing becomes more of a chore if you know you're going to have to chase down money, so make it less daunting by picking clients who pay on time.
Know where your money is
When it comes time to invoice, you don't want to find yourself asking, "So what money am I owed?" Again, if you're using Quickbooks, or similar accounting software, they will keep track of your money for you. If you're using Excel, add a column that says, "Date Paid," so that you can keep track of outstanding payments.