Any suggestions for building an easy-to-follow invoicing system that helps with unpaid invoices?

Freelancing has been a journey, but keeping track of invoices is a struggle. I often miss following up on overdue payments for too long.

I’m aiming to create a straightforward system that I can actually use—simple yet effective in tracking those clients who overlook their debts.

Build a system that runs on autopilot. Here’s what works:

  • Invoice the same week monthly (I use first Tuesday)
  • Write follow-up dates in red pen on your copy
  • Check overdue accounts every Monday with your coffee

Make it boring and predictable. I used to stress about follow-ups, now I just send: “Hi [name], checking on invoice #123 from [date]. Questions?”

No apologies or long explanations. Most people just forgot or lost the invoice. A quick nudge works.

Charge late fees. Even $25 gets attention. Put it in your contract upfront - no surprises.

Lost track of a $3k invoice for three months - learned that lesson fast.

Now I mark two dates on my calendar for every invoice: due date and follow-up date (5 days later). When follow-up day comes, I shoot them a quick email asking if they need anything to process payment.

Make it automatic so you don’t have to think about it. I also set payment terms upfront now instead of hoping clients pay on time. Most people are fine with a clear 15 or 30 day window.

Once you fall behind on follow-ups, it gets awkward to suddenly call about old invoices. Stay on top of it from the start.

I send out three copies of each invoice. Keep one for my files, client gets one, and the third goes in a folder sorted by due date. Every Friday I check what’s due in two weeks and shoot a quick reminder email. Payment comes in? Toss that third copy. Anything left in the folder gets a phone call the day after it’s late. No fancy software needed.

Use a simple spreadsheet to track invoices and due dates. Set calendar reminders for a week after a payment is due.

If 30 days pass without payment, call the client instead of relying on email. You’ll likely get a quicker response.

I keep it basic with a notepad and checklists.