Shoutout to the worst week of my freelance billing life

Honestly, last Monday I sent out 12 invoices for my small bookkeeping side gig and by Friday, 9 of them bounced back or got 'delayed'. One client literally said 'oh I thought you were joking about the $175 fee for that report.' I spent like 4 hours on the phone with PayPal and my bank trying to sort out why payments weren't clearing. Then on Thursday, I realized I forgot to bill a recurring $220 monthly retainer for 3 months straight because I got lazy with my spreadsheet. It was a total mess that made me question if I even know how to run a business. Has anyone else had a week where your billing system just completely failed you?

3 comments

3 Comments

janarivera1mo ago

12 invoices and only 3 cleared by Friday? I gotta say I see it differently than Jenny. Automatic recurring invoices sound good on paper but in my experience they just make it easier to ignore the fact that clients aren't paying. I had a similar week last year where I set up auto-invoices for 5 clients and by month 3 I had $800 in unpaid invoices because I never checked if they actually went through. One client told me their spam filter ate all the auto-generated emails for 2 months. Now I send every invoice manually with a specific subject line and a separate text message reminder. It takes more time per invoice but I catch issues on Tuesday instead of Friday.

lopez.quinn1mo ago

Right there with you. Manual invoicing catches way more problems automatically.

jenny_hall1mo ago

Hey have you tried setting up automatic recurring invoices? That saved me after a similar mess with my monthly retainers.