When I began freelance writing, a very sage mentor told me, “Just find a client. The rest of your business will work itself out.” And she was totally right. I had been spending way too much time gathering my writing samples, collecting testimonials, and perfecting my website, but none of that was doing me any good until I actually convinced a client to pay me for writing.

When it came time to invoice, I dug up a Microsoft Word template, modified it to suit my needs and emailed that to him. Pretty soon a check for $100 bucks arrived. Yay! I was doing something right.

But after awhile – when jobs started coming in and invoicing started flying out of my inbox – I realized that I wasn’t doing the greatest job keeping track of who owed me money, how much I could expect to come in by rent time, and who was taking the money and running.

I realized that my business was growing and I couldn’t get by on just winging it anymore. Here’s what I learned.

Keep it Simple

When a client receives your invoice, a few simple things should be readily apparent: who you are, how much they owe you, when it’s due and why they owe you this much (i.e. what you did for them). Be especially diligent about the latter – if problems ever arise you should both be able to refer back to your invoice and know why it was sent. Keep these four things in mind and you should never have any trouble with angry clients.

Keep Track of Who Owes You What

When you’re young and starving this isn’t hard – you notice when the money from those first few writing gigs hasn’t hit your pocket yet because you have unpaid invoices. But as your business grows and you have more and more invoices sitting out there in accounts payable departments sprouting mold, things can get trickier. Make sure you know who has paid you, who owes you but is getting to it, and who needs a gentle reminder.

Specify Your Late Fee on Every Invoice

If I recall correctly, my very first freelance agreement specified a late fee of 1.5% for every 30 days the invoice wasn’t paid.  But it wasn’t until I decided to revamp my invoicing system that I realized I’d never actually specified this late fee on my invoices. Remember, the person who actually pays you is often different from the person who signed your freelance agreement in the first place. Make sure they know there will be penalties for failing to pay so you don’t end up in the “when I get to it” pile.

Ask Clients How they Want You To Invoice

As I mentioned before, my very first invoices were ugly Microsoft Word templates. Well guess what? I still use those templates for one client to this very day. When I tried to update him to electronic invoices he resisted. The first time I sprang a new style invoice on this client, he wrote back a simple, “Let’s please go back to the old invoices.” And so we did. It may take me an extra minute or two to write up this old school invoice, but better me taking a little more time to invoice him than him taking a lot more time to pay me because I send him invoices in a way that’s unnatural to him.

Invoice Electronically

Most online invoicing services take care of #’s 1-4 above. They keep track of when you sent invoices to whom. They look professional. They allow you to add in a late penalty, and they offer a one-stop-dashboard where you can login and see the state of your business’s financial health. Better yet, they save a lot of time manually filling out invoices in your old school Microsoft Word template.

I’m curious – what was your very first invoice like?